This is redundant now

* Changelog v3.3.1 - GHA

* Update changelog for paperless-ngx 3.3.1

Removed MARIADB_HOST documentation from MariaDB compose files.

---------

Co-authored-by: github-actions <41898282+github-actions[bot]@users.noreply.github.com>
Co-authored-by: shamoon <4887959+shamoon@users.noreply.github.com>

.github/ISSUE_TEMPLATE/bug-report.yml

@@ -31,9 +31,19 @@ body:
       value: |
         #### 🤖 Use of AI tools
 
-        If this report was generated, in whole or in part, by an AI tool or agent you **must** clearly say so in the description below. Failing to clearly disclose this is a violation of our [Code of Conduct](https://github.com/paperless-ngx/paperless-ngx/blob/main/CODE_OF_CONDUCT.md).
+        If this report was generated, in whole or in part, by an AI tool or agent you **must** say so using the field below. Failing to clearly disclose this is a violation of our [Code of Conduct](https://github.com/paperless-ngx/paperless-ngx/blob/main/CODE_OF_CONDUCT.md).
 
         Reports written by an AI agent must describe the _observed behavior only_: what happened, how to reproduce it, logs etc. Do **not** include code analysis, speculation about the root cause, or suggest code fixes.
+  - type: dropdown
+    id: ai-usage
+    attributes:
+      label: AI usage
+      description: Was any part of this report written by an AI tool or agent?
+      options:
+        - No AI tools were used
+        - Yes, AI tools helped write this report
+    validations:
+      required: true
   - type: textarea
     id: description
     attributes:

.github/workflows/issue-bot.yml

@@ -43,6 +43,12 @@ jobs:
             const haystack = `${issue.title}\n${issue.body ?? ''}`;
             const honeypot = haystack.toUpperCase().includes('ASLOP-PR-VERIFY');
 
+            // The form's required "AI usage" dropdown renders as a `### AI usage` section. An agent
+            // that follows the template trips the honeypot even when it discloses, so only treat
+            // the honeypot as undisclosed AI use when the reporter did not answer "Yes" here.
+            const aiUsage = (issue.body ?? '').match(/^###\s+AI usage\s*\n+\s*(.+?)\s*$/m)?.[1] ?? '';
+            const disclosedAI = aiUsage.toLowerCase().startsWith('yes');
+
             // Issues opened through the form always get the template's default labels. GitHub
             // applies them a second or two *after* creation, so re-read them instead of trusting
             // the webhook payload, and retry before concluding that there are none.
@@ -55,19 +61,29 @@ jobs:
               if (labels.some((label) => templateLabels.includes(label))) break;
             }
             const bypassedTemplate = !labels.some((label) => templateLabels.includes(label));
-            core.info(`Labels: [${labels.join(', ')}], honeypot: ${honeypot}, bypassed template: ${bypassedTemplate}`);
+            core.info(
+              `Labels: [${labels.join(', ')}], honeypot: ${honeypot}, AI usage: "${aiUsage}", ` +
+                `bypassed template: ${bypassedTemplate}`
+            );
 
-            if (!honeypot && !bypassedTemplate) {
+            if (!bypassedTemplate && (disclosedAI || !honeypot)) {
+              if (disclosedAI) {
+                core.info('AI use disclosed, labeling only');
+                await github.rest.issues.addLabels({ ...common, labels: ['ai'] });
+              } else {
                 core.info('No slop signals found');
+              }
               return;
             }
 
-            // The honeypot is only ever tripped deliberately, so that message can name the cause.
+            // Reaching here with the honeypot means AI usage was not disclosed in the form, so that
+            // message can name the cause.
             // A missing template label only tells us the issue did not come from the form, which
             // is reason enough to close it, but not proof of how it was written.
             const body = honeypot
               ? 'This issue was automatically closed because it contains a marker that is only visible to ' +
-                'automated tools, which indicates it was generated by an AI agent without being disclosed as such.\n\n' +
+                'automated tools, which indicates it was generated by an AI agent, but the "AI usage" field does not ' +
+                'disclose this.\n\n' +
                 `Please see our [contributing guidelines](${contributing}) and [Code of Conduct](${codeOfConduct}). ` +
                 'You are welcome to open a new issue that describes the problem you observed in your own words.'
               : 'This issue was automatically closed because it was not opened using our bug report form. ' +

.mypy-baseline.txt

@@ -38,7 +38,6 @@ src/documents/bulk_edit.py:0: error: Incompatible types in assignment (expressio
 src/documents/bulk_edit.py:0: error: Invalid index type "str" for "dict[FieldDataType, str]"; expected type "FieldDataType"  [index]
 src/documents/bulk_edit.py:0: error: List comprehension has incompatible type List[tuple[int, Any]]; expected List[int]  [misc]
 src/documents/bulk_edit.py:0: error: List comprehension has incompatible type List[tuple[int, None]]; expected List[int]  [misc]
-src/documents/bulk_edit.py:0: error: Missing named argument "p" for "remove" of "PageList"  [call-arg]
 src/documents/bulk_edit.py:0: error: Missing type arguments for generic type "dict"  [type-arg]
 src/documents/bulk_edit.py:0: error: Missing type arguments for generic type "dict"  [type-arg]
 src/documents/bulk_edit.py:0: error: Need type annotation for "to_create" (hint: "to_create: list[<type>] = ...")  [var-annotated]

.pyrefly-baseline.json

@@ -91,13 +91,6 @@
       "concise_description": "Argument `list[int]` is not assignable to parameter `args` with type `tuple[Any, ...] | None` in function `celery.app.task.Task.apply_async`",
       "severity": "error"
     },
-    {
-      "column": 33,
-      "path": "src/documents/bulk_edit.py",
-      "name": "missing-argument",
-      "concise_description": "Missing argument `p` in function `pikepdf._core.PageList.remove`",
-      "severity": "error"
-    },
     {
       "column": 25,
       "path": "src/documents/caching.py",

docs/changelog.md

@@ -1,5 +1,54 @@
 # Changelog
 
+## paperless-ngx 3.3.1
+
+### Bug Fixes
+
+- Fix: use a root document's effective content for the LLM index and pr… [@stumpylog](https://github.com/stumpylog) ([#14423](https://github.com/paperless-ngx/paperless-ngx/pull/14423))
+- Fix: index document versions as their root document [@stumpylog](https://github.com/stumpylog) ([#14422](https://github.com/paperless-ngx/paperless-ngx/pull/14422))
+- Fix: authorize document versions by their root in the single-object permission check [@stumpylog](https://github.com/stumpylog) ([#14421](https://github.com/paperless-ngx/paperless-ngx/pull/14421))
+- Fix: Provide better error messages to users for invalid JSON [@stumpylog](https://github.com/stumpylog) ([#14419](https://github.com/paperless-ngx/paperless-ngx/pull/14419))
+- Fix: authorize document versions by their root and speed up permission id sets [@stumpylog](https://github.com/stumpylog) ([#14396](https://github.com/paperless-ngx/paperless-ngx/pull/14396))
+- Chore: update the db options warning [@shamoon](https://github.com/shamoon) ([#14398](https://github.com/paperless-ngx/paperless-ngx/pull/14398))
+- Fix: bulk reprocess latest version for root documents [@shamoon](https://github.com/shamoon) ([#14385](https://github.com/paperless-ngx/paperless-ngx/pull/14385))
+- Fix: consistently use root doc for version action permissions [@shamoon](https://github.com/shamoon) ([#14384](https://github.com/paperless-ngx/paperless-ngx/pull/14384))
+- Fix: Don't attempt to index created dates which are not representable in the FTS index [@stumpylog](https://github.com/stumpylog) ([#14390](https://github.com/paperless-ngx/paperless-ngx/pull/14390))
+- Fix: retry a search index rebuild that was interrupted [@stumpylog](https://github.com/stumpylog) ([#14379](https://github.com/paperless-ngx/paperless-ngx/pull/14379))
+
+### Documentation
+
+- Chore: silence gotenberg startup warning [@slankes](https://github.com/slankes) ([#14405](https://github.com/paperless-ngx/paperless-ngx/pull/14405))
+- Documentation: remove MARIADB\_HOST from MariaDB compose files [@shamoon](https://github.com/shamoon) ([#14378](https://github.com/paperless-ngx/paperless-ngx/pull/14378))
+- Documentation: Updates the troubleshooting with 2 common database collation issues [@stumpylog](https://github.com/stumpylog) ([#14370](https://github.com/paperless-ngx/paperless-ngx/pull/14370))
+
+### Maintenance
+
+- Chore: Upgrade runners to Ubuntu 26.04 [@stumpylog](https://github.com/stumpylog) ([#14347](https://github.com/paperless-ngx/paperless-ngx/pull/14347))
+
+### Dependencies
+
+- Chore(deps): Bump the npm\_and\_yarn group across 1 directory with 2 updates @[dependabot[bot]](https://github.com/apps/dependabot) ([#14417](https://github.com/paperless-ngx/paperless-ngx/pull/14417))
+
+### All App Changes
+
+<details>
+<summary>12 changes</summary>
+
+- Chore: share the authorizing owner rule between the id sets and the trash filter [@stumpylog](https://github.com/stumpylog) ([#14425](https://github.com/paperless-ngx/paperless-ngx/pull/14425))
+- Fix: use a root document's effective content for the LLM index and pr… [@stumpylog](https://github.com/stumpylog) ([#14423](https://github.com/paperless-ngx/paperless-ngx/pull/14423))
+- Fix: index document versions as their root document [@stumpylog](https://github.com/stumpylog) ([#14422](https://github.com/paperless-ngx/paperless-ngx/pull/14422))
+- Fix: authorize document versions by their root in the single-object permission check [@stumpylog](https://github.com/stumpylog) ([#14421](https://github.com/paperless-ngx/paperless-ngx/pull/14421))
+- Fix: Provide better error messages to users for invalid JSON [@stumpylog](https://github.com/stumpylog) ([#14419](https://github.com/paperless-ngx/paperless-ngx/pull/14419))
+- Chore(deps): Bump the npm\_and\_yarn group across 1 directory with 2 updates @[dependabot[bot]](https://github.com/apps/dependabot) ([#14417](https://github.com/paperless-ngx/paperless-ngx/pull/14417))
+- Fix: authorize document versions by their root and speed up permission id sets [@stumpylog](https://github.com/stumpylog) ([#14396](https://github.com/paperless-ngx/paperless-ngx/pull/14396))
+- Chore: update the db options warning [@shamoon](https://github.com/shamoon) ([#14398](https://github.com/paperless-ngx/paperless-ngx/pull/14398))
+- Fix: bulk reprocess latest version for root documents [@shamoon](https://github.com/shamoon) ([#14385](https://github.com/paperless-ngx/paperless-ngx/pull/14385))
+- Fix: consistently use root doc for version action permissions [@shamoon](https://github.com/shamoon) ([#14384](https://github.com/paperless-ngx/paperless-ngx/pull/14384))
+- Fix: Don't attempt to index created dates which are not representable in the FTS index [@stumpylog](https://github.com/stumpylog) ([#14390](https://github.com/paperless-ngx/paperless-ngx/pull/14390))
+- Fix: retry a search index rebuild that was interrupted [@stumpylog](https://github.com/stumpylog) ([#14379](https://github.com/paperless-ngx/paperless-ngx/pull/14379))
+
+</details>
+
 ## paperless-ngx 3.3.0
 
 ### Features / Enhancements

src/documents/bulk_edit.py

@@ -3,6 +3,7 @@ from __future__ import annotations
 import logging
 import tempfile
 import uuid
+from functools import partial
 from pathlib import Path
 from typing import TYPE_CHECKING
 from typing import Literal
@@ -23,6 +24,7 @@ from django.db.models import When
 from django.db.models.functions import Coalesce
 from django.utils import timezone
 
+from documents import pdf_ops
 from documents.data_models import ConsumableDocument
 from documents.data_models import DocumentMetadataOverrides
 from documents.data_models import DocumentSource
@@ -123,6 +125,11 @@ def _resolve_root_and_source_doc(
     )
 
 
+def _scratch_path(name: str) -> Path:
+    """A path inside a fresh directory under SCRATCH_DIR."""
+    return Path(tempfile.mkdtemp(dir=settings.SCRATCH_DIR)) / name
+
+
 def set_correspondent(
     doc_ids: list[int],
     correspondent: Correspondent,
@@ -499,8 +506,6 @@ def rotate(
         pair = _resolve_root_and_source_doc(doc, source_mode=source_mode)
         docs_by_root_id.setdefault(pair.root_doc.id, pair)
 
-    import pikepdf
-
     for pair in docs_by_root_id.values():
         if pair.source_doc.mime_type != "application/pdf":
             logger.warning(
@@ -513,11 +518,7 @@ def rotate(
                 Path(tempfile.mkdtemp(dir=settings.SCRATCH_DIR))
                 / f"{pair.root_doc.id}_rotated.pdf"
             )
-            with pikepdf.open(pair.source_doc.source_path) as pdf:
+            pdf_ops.rotate_pdf(pair.source_doc.source_path, filepath, degrees)
-                for page in pdf.pages:
-                    page.rotate(degrees, relative=True)
-                pdf.remove_unreferenced_resources()
-                pdf.save(filepath)
 
             # Preserve metadata/permissions via overrides; mark as new version
             overrides = DocumentMetadataOverrides().from_document(pair.root_doc)
@@ -560,11 +561,8 @@ def merge(
     qs = Document.objects.select_related("root_document").filter(id__in=doc_ids)
     docs_by_id = {doc.id: doc for doc in qs}
     affected_docs: list[int] = []
-    import pikepdf
-
-    merged_pdf = pikepdf.new()
-    version: str = merged_pdf.pdf_version
     handoff_asn: int | None = None
+    with pdf_ops.PdfMerger() as merger:
         # use doc_ids to preserve order
         for doc_id in doc_ids:
             doc = docs_by_id.get(doc_id)
@@ -572,16 +570,18 @@ def merge(
                 continue
             pair = _resolve_root_and_source_doc(doc, source_mode=source_mode)
             try:
-            doc_path = (
+                # archive_path is None when there is no archive version
+                archive_path = (
                     pair.source_doc.archive_path
                     if archive_fallback
                     and pair.source_doc.mime_type != "application/pdf"
-                and pair.source_doc.has_archive_version
+                    else None
-                else pair.source_doc.source_path
+                )
+                merger.add(
+                    archive_path
+                    if archive_path is not None
+                    else pair.source_doc.source_path,
                 )
-            with pikepdf.open(str(doc_path)) as pdf:
-                version = max(version, pdf.pdf_version)
-                merged_pdf.pages.extend(pdf.pages)
                 affected_docs.append(doc.id)
                 if handoff_asn is None and doc.archive_serial_number is not None:
                     handoff_asn = doc.archive_serial_number
@@ -599,9 +599,7 @@ def merge(
             )
             / f"{'_'.join([str(doc_id) for doc_id in affected_docs])[:100]}_merged.pdf"
         )
-    merged_pdf.remove_unreferenced_resources()
+        merger.save(filepath)
-    merged_pdf.save(filepath, min_version=version)
-    merged_pdf.close()
 
     if metadata_document_id:
         metadata_document = qs.get(id=metadata_document_id)
@@ -777,26 +775,22 @@ def split(
     )
     doc = Document.objects.select_related("root_document").get(id=doc_ids[0])
     pair = _resolve_root_and_source_doc(doc, source_mode=source_mode)
-    import pikepdf
 
     consume_tasks = []
 
     try:
-        with pikepdf.open(pair.source_doc.source_path) as pdf:
+        outputs = [
-            for idx, split_doc in enumerate(pages):
+            (
-                dst: pikepdf.Pdf = pikepdf.new()
+                [pdf_ops.PageSpec(page) for page in split_doc],
-                for page in split_doc:
+                partial(_scratch_path, f"{doc.id}_{split_doc[0]}-{split_doc[-1]}.pdf"),
-                    dst.pages.append(pdf.pages[page - 1])
-                filepath: Path = (
-                    Path(
-                        tempfile.mkdtemp(dir=settings.SCRATCH_DIR),
             )
-                    / f"{doc.id}_{split_doc[0]}-{split_doc[-1]}.pdf"
+            for split_doc in pages
-                )
+        ]
-                dst.remove_unreferenced_resources()
+        filepaths = pdf_ops.build_pdfs(pair.source_doc.source_path, outputs)
-                dst.save(filepath)
-                dst.close()
 
+        for idx, (split_doc, filepath) in enumerate(
+            zip(pages, filepaths, strict=True),
+        ):
             overrides: DocumentMetadataOverrides = (
                 DocumentMetadataOverrides().from_document(doc)
             )
@@ -855,8 +849,6 @@ def delete_pages(
     )
     doc = Document.objects.select_related("root_document").get(id=doc_ids[0])
     pair = _resolve_root_and_source_doc(doc, source_mode=source_mode)
-    pages = sorted(pages)  # sort pages to avoid index issues
-    import pikepdf
 
     try:
         # Produce edited PDF to a temp file and create a new version
@@ -864,13 +856,7 @@ def delete_pages(
             Path(tempfile.mkdtemp(dir=settings.SCRATCH_DIR))
             / f"{pair.root_doc.id}_pages_deleted.pdf"
         )
-        with pikepdf.open(pair.source_doc.source_path) as pdf:
+        pdf_ops.remove_pages(pair.source_doc.source_path, filepath, pages)
-            offset = 1  # pages are 1-indexed
-            for page_num in pages:
-                pdf.pages.remove(pdf.pages[page_num - offset])
-                offset += 1  # remove() changes the index of the pages
-            pdf.remove_unreferenced_resources()
-            pdf.save(filepath)
 
         overrides = DocumentMetadataOverrides().from_document(pair.root_doc)
         if user is not None:
@@ -919,47 +905,28 @@ def edit_pdf(
     )
     doc = Document.objects.select_related("root_document").get(id=doc_ids[0])
     pair = _resolve_root_and_source_doc(doc, source_mode=source_mode)
-    import pikepdf
-
-    pdf_docs: list[pikepdf.Pdf] = []
-
     try:
-        if not operations:
+        output_count = pdf_ops.validate_page_operations(
-            raise ValueError("Output document index is out of bounds")
+            operations,
-
+            single_output=update_document,
-        max_idx = max(op.get("doc", 0) for op in operations)
-        if update_document and max_idx > 0:
-            logger.error(
-                "Update requested but multiple output documents specified",
         )
-            raise ValueError("Multiple output documents specified")
+        page_specs: list[list[pdf_ops.PageSpec]] = [[] for _ in range(output_count)]
-
-        if any(
-            op.get("doc", 0) < 0 or op.get("doc", 0) >= len(operations)
-            for op in operations
-        ):
-            raise ValueError("Output document index is out of bounds")
-
-        with pikepdf.open(pair.source_doc.source_path) as src:
-            # prepare output documents
-            pdf_docs = [pikepdf.new() for _ in range(max_idx + 1)]
-
         for op in operations:
-                dst = pdf_docs[op.get("doc", 0)]
+            page_specs[op.get("doc", 0)].append(
-                page = src.pages[op["page"] - 1]
+                pdf_ops.PageSpec(op["page"], op.get("rotate", 0)),
-                dst.pages.append(page)
+            )
-                if op.get("rotate"):
-                    dst.pages[-1].rotate(op["rotate"], relative=True)
 
         if update_document:
             # Create a new version from the edited PDF rather than replacing in-place
-            pdf = pdf_docs[0]
+            (filepath,) = pdf_ops.build_pdfs(
-            pdf.remove_unreferenced_resources()
+                pair.source_doc.source_path,
-            filepath: Path = (
+                [
-                Path(tempfile.mkdtemp(dir=settings.SCRATCH_DIR))
+                    (
-                / f"{pair.root_doc.id}_edited.pdf"
+                        page_specs[0],
+                        partial(_scratch_path, f"{pair.root_doc.id}_edited.pdf"),
+                    ),
+                ],
             )
-            pdf.save(filepath)
             overrides = (
                 DocumentMetadataOverrides().from_document(pair.root_doc)
                 if include_metadata
@@ -980,6 +947,19 @@ def edit_pdf(
                 headers={"trigger_source": trigger_source},
             )
         else:
+            version_filepaths = pdf_ops.build_pdfs(
+                pair.source_doc.source_path,
+                [
+                    (
+                        specs,
+                        partial(
+                            _scratch_path,
+                            f"{pair.root_doc.id}_edit_{idx}.pdf",
+                        ),
+                    )
+                    for idx, specs in enumerate(page_specs, start=1)
+                ],
+            )
             consume_tasks = []
             overrides = (
                 DocumentMetadataOverrides().from_document(pair.root_doc)
@@ -991,15 +971,9 @@ def edit_pdf(
                 overrides.actor_id = user.id
             if not delete_original:
                 overrides.skip_asn_if_exists = True
-            if delete_original and len(pdf_docs) == 1:
+            if delete_original and output_count == 1:
                 overrides.asn = pair.root_doc.archive_serial_number
-            for idx, pdf in enumerate(pdf_docs, start=1):
+            for version_filepath in version_filepaths:
-                version_filepath: Path = (
-                    Path(tempfile.mkdtemp(dir=settings.SCRATCH_DIR))
-                    / f"{pair.root_doc.id}_edit_{idx}.pdf"
-                )
-                pdf.remove_unreferenced_resources()
-                pdf.save(version_filepath)
                 consume_tasks.append(
                     consume_file.s(
                         input_doc=ConsumableDocument(
@@ -1049,8 +1023,6 @@ def remove_password(
     """
     Remove password protection from PDF documents.
     """
-    import pikepdf
-
     for doc_id in doc_ids:
         doc = Document.objects.select_related("root_document").get(id=doc_id)
         pair = _resolve_root_and_source_doc(doc, source_mode=source_mode)
@@ -1064,26 +1036,19 @@ def remove_password(
                 doc.id,
                 pair.source_doc.source_path,
             )
-            try:
+            if not pdf_ops.needs_decrypt(source_path):
-                with pikepdf.open(source_path) as pdf:
-                    if not pdf.is_encrypted:
                 logger.info(
                     "Skipping password removal for document %s because the "
                     "source PDF is not encrypted",
                     pair.root_doc.id,
                 )
                 continue
-            except pikepdf.PasswordError:
-                # Password-protected PDFs need the supplied password below.
-                pass
 
-            with pikepdf.open(source_path, password=password) as pdf:
+            filepath = pdf_ops.decrypt_pdf(
-                filepath: Path = (
+                source_path,
-                    Path(tempfile.mkdtemp(dir=settings.SCRATCH_DIR))
+                partial(_scratch_path, f"{pair.root_doc.id}_unprotected.pdf"),
-                    / f"{pair.root_doc.id}_unprotected.pdf"
+                password,
             )
-                pdf.remove_unreferenced_resources()
-                pdf.save(filepath)
 
             if update_document:
                 # Create a new version rather than modifying the root/original in place.

src/documents/management/commands/document_exporter.py

@@ -514,8 +514,11 @@ class Command(CryptMixin, PaperlessCommand):
             else:
                 base_name = document.get_public_filename(counter=filename_counter)
 
-            if base_name not in self.exported_files:
+            # The thumbnail and archive names are derived from the stem, so
-                self.exported_files.add(base_name)
+            # uniqueness must hold without the original's extension
+            unique_key = str(Path(base_name).with_suffix(""))
+            if unique_key not in self.exported_files:
+                self.exported_files.add(unique_key)
                 break
             else:
                 filename_counter += 1

src/documents/pdf_ops.py

@@ -0,0 +1,194 @@
+"""
+Pure PDF page operations used by documents.bulk_edit.
+
+This module deliberately knows nothing about Django, Celery or the documents
+app: callers resolve documents, choose output paths and queue work. Every
+function that writes a PDF removes unreferenced resources before saving.
+
+pikepdf is always called as ``pikepdf.open(...)`` / ``pikepdf.new()`` (never
+``from pikepdf import open``) so tests can patch those module attributes.
+"""
+
+from __future__ import annotations
+
+from typing import TYPE_CHECKING
+from typing import NamedTuple
+
+import pikepdf
+
+if TYPE_CHECKING:
+    from collections.abc import Callable
+    from collections.abc import Iterable
+    from collections.abc import Mapping
+    from collections.abc import Sequence
+    from pathlib import Path
+    from types import TracebackType
+
+
+class PageSpec(NamedTuple):
+    """One page of an output PDF: a 1-indexed source page, optionally rotated."""
+
+    page: int
+    rotate: int = 0  # relative degrees, 0 leaves the page alone
+
+
+def _require_positive(pages: Iterable[int]) -> None:
+    for page in pages:
+        if page < 1:
+            raise ValueError(f"Page numbers start at 1, got {page}")
+
+
+def rotate_pdf(src: Path, dst: Path, degrees: int) -> None:
+    """
+    Rotate every page relatively on the opened document, not a rebuild, so Info,
+    XMP and outlines are kept. ``src`` is not modified.
+    """
+    with pikepdf.open(src) as pdf:
+        for page in pdf.pages:
+            page.rotate(degrees, relative=True)
+        pdf.remove_unreferenced_resources()
+        pdf.save(dst)
+
+
+def remove_pages(src: Path, dst: Path, pages: Iterable[int]) -> None:
+    """
+    Remove 1-indexed pages from the opened document, not a rebuild, so Info, XMP
+    and outlines are kept. ``src`` is not modified.
+
+    Duplicates are ignored. Pages are removed highest first so earlier removals
+    never shift the index of later ones.
+    """
+    unique = sorted(set(pages))
+    _require_positive(unique)
+    with pikepdf.open(src) as pdf:
+        for page_num in reversed(unique):
+            del pdf.pages[page_num - 1]
+        pdf.remove_unreferenced_resources()
+        pdf.save(dst)
+
+
+def build_pdfs(
+    src: Path,
+    outputs: Sequence[tuple[Sequence[PageSpec], Callable[[], Path]]],
+) -> list[Path]:
+    """
+    Build one new PDF per output from pages of ``src``, opening ``src`` once.
+
+    Each output is ``(page_specs, make_dst)``. Every page number is checked against
+    ``src`` before any output is built, and ``make_dst`` is called after that
+    output's pages are copied and immediately before it is saved, so a bad page
+    number in any output never leaves a destination behind. Document-level data
+    (Info, XMP, outlines) is not carried over. Returns the written paths in output
+    order.
+    """
+    for specs, _ in outputs:
+        _require_positive(spec.page for spec in specs)
+
+    written: list[Path] = []
+    with pikepdf.open(src) as source:
+        page_count = len(source.pages)
+        for specs, _ in outputs:
+            for spec in specs:
+                if spec.page > page_count:
+                    raise IndexError(
+                        f"Page {spec.page} is out of range, the PDF has "
+                        f"{page_count} pages",
+                    )
+        for specs, make_dst in outputs:
+            dst = pikepdf.new()
+            for spec in specs:
+                dst.pages.append(source.pages[spec.page - 1])
+                if spec.rotate:
+                    dst.pages[-1].rotate(spec.rotate, relative=True)
+            dst.remove_unreferenced_resources()
+            path = make_dst()
+            dst.save(path)
+            dst.close()
+            written.append(path)
+    return written
+
+
+def validate_page_operations(
+    operations: Sequence[Mapping[str, int]],
+    *,
+    single_output: bool,
+) -> int:
+    """
+    Validate ``edit_pdf`` style operations and return the output document count.
+
+    Each operation has ``page`` and optionally ``rotate`` and ``doc`` (the output
+    document index, default 0). The bounds rule is kept as it was: a ``doc`` index
+    must be below the number of operations.
+    """
+    if not operations:
+        raise ValueError("Output document index is out of bounds")
+
+    max_idx = max(op.get("doc", 0) for op in operations)
+    if single_output and max_idx > 0:
+        raise ValueError("Multiple output documents specified")
+
+    if any(
+        op.get("doc", 0) < 0 or op.get("doc", 0) >= len(operations) for op in operations
+    ):
+        raise ValueError("Output document index is out of bounds")
+
+    return max_idx + 1
+
+
+def needs_decrypt(src: Path) -> bool:
+    """
+    True if ``src`` is encrypted. A PDF that needs a password to open at all
+    counts as encrypted.
+    """
+    try:
+        with pikepdf.open(src) as pdf:
+            return bool(pdf.is_encrypted)
+    except pikepdf.PasswordError:
+        return True
+
+
+def decrypt_pdf(src: Path, make_dst: Callable[[], Path], password: str) -> Path:
+    """
+    Write an unencrypted copy of ``src`` and return its path.
+
+    ``make_dst`` is only called once the password has been accepted, so a wrong
+    password never leaves a destination behind.
+    """
+    with pikepdf.open(src, password=password) as pdf:
+        pdf.remove_unreferenced_resources()
+        dst = make_dst()
+        pdf.save(dst)
+    return dst
+
+
+class PdfMerger:
+    """
+    Accumulates the pages of several PDFs into one new PDF.
+
+    ``add`` raises if a source cannot be read; deciding whether to skip it is the
+    caller's policy. Use as a context manager so the merged PDF is closed.
+    """
+
+    def __init__(self) -> None:
+        self._pdf = pikepdf.new()
+        self._version: str = self._pdf.pdf_version
+
+    def __enter__(self) -> PdfMerger:
+        return self
+
+    def __exit__(
+        self,
+        exc_type: type[BaseException] | None,
+        exc: BaseException | None,
+        tb: TracebackType | None,
+    ) -> None:
+        self._pdf.close()
+
+    def add(self, path: Path) -> None:
+        with pikepdf.open(str(path)) as pdf:
+            self._version = max(self._version, pdf.pdf_version)
+            self._pdf.pages.extend(pdf.pages)
+
+    def save(self, dst: Path) -> None:
+        self._pdf.remove_unreferenced_resources()
+        self._pdf.save(dst, min_version=self._version)

src/documents/serialisers.py

@@ -2144,6 +2144,8 @@ class BulkEditSerializer(
             raise serializers.ValidationError("pages must be a list")
         if not all(isinstance(i, int) for i in parameters["pages"]):
             raise serializers.ValidationError("pages must be a list of integers")
+        if any(i < 1 for i in parameters["pages"]):
+            raise serializers.ValidationError("pages must be positive integers")
 
     def _validate_parameters_merge(self, parameters) -> None:
         if "delete_originals" in parameters:

src/documents/tests/test_api_bulk_edit.py

@@ -1843,6 +1843,36 @@ class TestBulkEditAPI(DirectoriesMixin, APITestCase):
         m.assert_called_once()
         self.assertEqual(m.call_args.kwargs["pages"], [[1], [2, 3, 4], [5]])
 
+    @mock.patch("documents.serialisers.bulk_edit.delete_pages")
+    def test_bulk_edit_delete_pages_rejects_pages_below_one(self, m) -> None:
+        """
+        GIVEN:
+            - A legacy delete_pages bulk edit
+        WHEN:
+            - API to bulk edit is called with a page number below 1
+        THEN:
+            - API returns HTTP 400
+            - delete_pages is not called
+        """
+        self.setup_mock(m, "delete_pages")
+
+        for pages in ([0], [-1], [1, 0]):
+            with self.subTest(pages=pages):
+                response = self.client.post(
+                    "/api/documents/bulk_edit/",
+                    json.dumps(
+                        {
+                            "documents": [self.doc2.id],
+                            "method": "delete_pages",
+                            "parameters": {"pages": pages},
+                        },
+                    ),
+                    content_type="application/json",
+                )
+                self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+                self.assertIn(b"pages must be positive integers", response.content)
+        m.assert_not_called()
+
     @mock.patch("documents.views.bulk_edit.rotate")
     def test_rotate_insufficient_permissions(self, m) -> None:
         self.doc1.owner = User.objects.get(username="temp_admin")

src/documents/tests/test_bulk_edit.py

@@ -1,9 +1,9 @@
 import shutil
+from collections.abc import Callable
 from datetime import date
 from pathlib import Path
 from unittest import mock
 
-import pikepdf
 import pytest
 from django.contrib.auth.models import Group
 from django.contrib.auth.models import Permission
@@ -23,6 +23,7 @@ from documents.models import Document
 from documents.models import DocumentType
 from documents.models import StoragePath
 from documents.models import Tag
+from documents.pdf_ops import PageSpec
 from documents.permissions import set_permissions_for_objects
 from paperless_testing.dirs import DirectoriesMixin
 from paperless_testing.factories import DocumentFactory
@@ -796,16 +797,14 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         self.img_doc.save()
 
     @staticmethod
-    def mock_password_required_pdf(
+    def fake_decrypt(
-        mock_open: mock.Mock,
+        src: Path,
-        fake_pdf: mock.Mock,
+        make_dst: Callable[[], Path],
-    ) -> None:
+        password: str,
-        password_context = mock.MagicMock()
+    ) -> Path:
-        password_context.__enter__.return_value = fake_pdf
+        dst = make_dst()
-        mock_open.side_effect = [
+        dst.write_bytes(b"password removed")
-            pikepdf.PasswordError("password required"),
+        return dst
-            password_context,
-        ]
 
     @mock.patch("documents.tasks.consume_file.s")
     def test_merge(self, mock_consume_file) -> None:
@@ -850,12 +849,12 @@ class TestPDFActions(DirectoriesMixin, TestCase):
 
         self.assertEqual(result, "OK")
 
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.PdfMerger")
     @mock.patch("documents.tasks.consume_file.s")
     def test_merge_uses_latest_version_source_for_root_selection(
         self,
         mock_consume_file,
-        mock_open_pdf,
+        mock_merger,
     ) -> None:
         version_file = self.dirs.scratch_dir / "sample2_version_merge.pdf"
         shutil.copy(self.doc2.source_path, version_file)
@@ -866,16 +865,14 @@ class TestPDFActions(DirectoriesMixin, TestCase):
             filename=version_file,
             mime_type="application/pdf",
         )
-        fake_pdf = mock.MagicMock()
+        merger = mock_merger.return_value.__enter__.return_value
-        fake_pdf.pdf_version = "1.7"
+        merger.save.side_effect = lambda dst: shutil.copy(version.source_path, dst)
-        fake_pdf.pages = [mock.Mock()]
-        mock_open_pdf.return_value.__enter__.return_value = fake_pdf
 
         result = bulk_edit.merge([self.doc2.id])
 
         self.assertEqual(result, "OK")
-        mock_open_pdf.assert_called_once_with(str(version.source_path))
+        merger.add.assert_called_once_with(version.source_path)
-        mock_consume_file.assert_not_called()
+        mock_consume_file.assert_called_once()
 
     @mock.patch("documents.bulk_edit.delete.si")
     @mock.patch("documents.tasks.consume_file.s")
@@ -1037,18 +1034,18 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
     @mock.patch("documents.tasks.consume_file.delay")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.PdfMerger.add")
-    def test_merge_with_errors(self, mock_open_pdf, mock_consume_file) -> None:
+    def test_merge_with_errors(self, mock_add, mock_consume_file) -> None:
         """
         GIVEN:
             - Existing documents
         WHEN:
             - Merge action is called with 2 documents
-            - Error occurs when opening both files
+            - Error occurs when adding both files
         THEN:
             - Consume file should not be called
         """
-        mock_open_pdf.side_effect = Exception("Error opening PDF")
+        mock_add.side_effect = Exception("Error opening PDF")
         doc_ids = [self.doc2.id, self.doc3.id]
 
         with self.assertLogs("paperless.bulk_edit", level="ERROR") as cm:
@@ -1085,12 +1082,12 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         self.assertEqual(result, "OK")
 
     @mock.patch("documents.bulk_edit.group")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.build_pdfs")
     @mock.patch("documents.tasks.consume_file.s")
     def test_split_uses_latest_version_source_for_root_selection(
         self,
         mock_consume_file,
-        mock_open_pdf,
+        mock_build_pdfs,
         mock_group,
     ) -> None:
         version_file = self.dirs.scratch_dir / "sample2_version_split.pdf"
@@ -1102,17 +1099,15 @@ class TestPDFActions(DirectoriesMixin, TestCase):
             filename=version_file,
             mime_type="application/pdf",
         )
-        fake_pdf = mock.MagicMock()
+        mock_build_pdfs.return_value = [version.source_path, version.source_path]
-        fake_pdf.pages = [mock.Mock(), mock.Mock()]
-        mock_open_pdf.return_value.__enter__.return_value = fake_pdf
         mock_group.return_value.delay.return_value = None
 
         result = bulk_edit.split([self.doc2.id], [[1], [2]])
 
         self.assertEqual(result, "OK")
-        mock_open_pdf.assert_called_once_with(version.source_path)
+        self.assertEqual(mock_build_pdfs.call_args.args[0], version.source_path)
-        mock_consume_file.assert_not_called()
+        self.assertEqual(mock_consume_file.call_count, 2)
-        mock_group.return_value.delay.assert_not_called()
+        mock_group.return_value.delay.assert_called_once()
 
     @mock.patch("documents.bulk_edit.delete.si")
     @mock.patch("documents.tasks.consume_file.s")
@@ -1200,18 +1195,18 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         self.assertEqual(self.doc2.archive_serial_number, 222)
 
     @mock.patch("documents.tasks.consume_file.apply_async")
-    @mock.patch("pikepdf.Pdf.save")
+    @mock.patch("documents.pdf_ops.build_pdfs")
-    def test_split_with_errors(self, mock_save_pdf, mock_consume_file) -> None:
+    def test_split_with_errors(self, mock_build_pdfs, mock_consume_file) -> None:
         """
         GIVEN:
             - Existing documents
         WHEN:
             - Split action is called with 1 document and 2 page groups
-            - Error occurs when saving the files
+            - Error occurs when building the files
         THEN:
             - Consume file should not be called
         """
-        mock_save_pdf.side_effect = Exception("Error saving PDF")
+        mock_build_pdfs.side_effect = Exception("Error building PDFs")
         doc_ids = [self.doc2.id]
         pages = [[1, 2], [3]]
 
@@ -1246,10 +1241,10 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         self.assertEqual(result, "OK")
 
     @mock.patch("documents.tasks.consume_file.apply_async")
-    @mock.patch("pikepdf.Pdf.save")
+    @mock.patch("documents.pdf_ops.rotate_pdf")
     def test_rotate_with_error(
         self,
-        mock_pdf_save,
+        mock_rotate_pdf,
         mock_consume_delay,
     ) -> None:
         """
@@ -1257,11 +1252,11 @@ class TestPDFActions(DirectoriesMixin, TestCase):
             - Existing documents
         WHEN:
             - Rotate action is called with 2 documents
-            - PikePDF raises an error
+            - Rotating the PDF raises an error
         THEN:
             - Rotate action should be called 0 times
         """
-        mock_pdf_save.side_effect = Exception("Error saving PDF")
+        mock_rotate_pdf.side_effect = Exception("Error rotating PDF")
         doc_ids = [self.doc2.id, self.doc3.id]
 
         with self.assertLogs("paperless.bulk_edit", level="ERROR") as cm:
@@ -1296,10 +1291,10 @@ class TestPDFActions(DirectoriesMixin, TestCase):
 
     @mock.patch("documents.data_models.magic.from_file", return_value="application/pdf")
     @mock.patch("documents.tasks.consume_file.apply_async")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.rotate_pdf")
     def test_rotate_explicit_selection_uses_root_source_when_root_selected(
         self,
-        mock_open,
+        mock_rotate_pdf,
         mock_consume_delay,
         mock_magic,
     ) -> None:
@@ -1308,9 +1303,6 @@ class TestPDFActions(DirectoriesMixin, TestCase):
             title="B version 1",
             root_document=self.doc2,
         )
-        fake_pdf = mock.MagicMock()
-        fake_pdf.pages = [mock.Mock()]
-        mock_open.return_value.__enter__.return_value = fake_pdf
 
         result = bulk_edit.rotate(
             [self.doc2.id],
@@ -1319,26 +1311,35 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
         self.assertEqual(result, "OK")
-        mock_open.assert_called_once_with(self.doc2.source_path)
+        self.assertEqual(mock_rotate_pdf.call_args.args[0], self.doc2.source_path)
         mock_consume_delay.assert_called_once()
 
     @mock.patch("documents.tasks.consume_file.apply_async")
-    @mock.patch("pikepdf.Pdf.save")
+    @mock.patch("documents.pdf_ops.remove_pages")
     @mock.patch("documents.data_models.magic.from_file", return_value="application/pdf")
-    def test_delete_pages(self, mock_magic, mock_pdf_save, mock_consume_delay) -> None:
+    def test_delete_pages(
+        self,
+        mock_magic,
+        mock_remove_pages,
+        mock_consume_delay,
+    ) -> None:
         """
         GIVEN:
             - Existing documents
         WHEN:
             - Delete pages action is called with 1 document and 2 pages
         THEN:
-            - Save should be called once
+            - The pages are removed from the document's source PDF
             - A new version should be enqueued via consume_file
         """
         doc_ids = [self.doc2.id]
         pages = [1, 3]
         result = bulk_edit.delete_pages(doc_ids, pages)
-        mock_pdf_save.assert_called_once()
+        mock_remove_pages.assert_called_once_with(
+            self.doc2.source_path,
+            mock.ANY,
+            [1, 3],
+        )
         mock_consume_delay.assert_called_once()
         task_kwargs = mock_consume_delay.call_args.kwargs["kwargs"]
         self.assertEqual(task_kwargs["input_doc"].root_document_id, self.doc2.id)
@@ -1350,10 +1351,10 @@ class TestPDFActions(DirectoriesMixin, TestCase):
 
     @mock.patch("documents.data_models.magic.from_file", return_value="application/pdf")
     @mock.patch("documents.tasks.consume_file.apply_async")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.remove_pages")
     def test_delete_pages_explicit_selection_uses_root_source_when_root_selected(
         self,
-        mock_open,
+        mock_remove_pages,
         mock_consume_delay,
         mock_magic,
     ) -> None:
@@ -1362,9 +1363,6 @@ class TestPDFActions(DirectoriesMixin, TestCase):
             title="B version 1",
             root_document=self.doc2,
         )
-        fake_pdf = mock.MagicMock()
-        fake_pdf.pages = [mock.Mock(), mock.Mock()]
-        mock_open.return_value.__enter__.return_value = fake_pdf
 
         result = bulk_edit.delete_pages(
             [self.doc2.id],
@@ -1373,23 +1371,26 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
         self.assertEqual(result, "OK")
-        mock_open.assert_called_once_with(self.doc2.source_path)
+        self.assertEqual(mock_remove_pages.call_args.args[0], self.doc2.source_path)
         mock_consume_delay.assert_called_once()
 
     @mock.patch("documents.tasks.consume_file.apply_async")
-    @mock.patch("pikepdf.Pdf.save")
+    @mock.patch("documents.pdf_ops.remove_pages")
-    def test_delete_pages_with_error(self, mock_pdf_save, mock_consume_delay) -> None:
+    def test_delete_pages_with_error(
+        self,
+        mock_remove_pages,
+        mock_consume_delay,
+    ) -> None:
         """
         GIVEN:
             - Existing documents
         WHEN:
             - Delete pages action is called with 1 document and 2 pages
-            - PikePDF raises an error
+            - Removing the pages raises an error
         THEN:
-            - Save should be called once
             - No new version should be enqueued
         """
-        mock_pdf_save.side_effect = Exception("Error saving PDF")
+        mock_remove_pages.side_effect = Exception("Error removing pages")
         doc_ids = [self.doc2.id]
         pages = [1, 3]
 
@@ -1419,6 +1420,41 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         self.assertEqual(result, "OK")
         mock_group.return_value.delay.assert_called_once()
 
+    @mock.patch("documents.bulk_edit.group")
+    @mock.patch("documents.pdf_ops.build_pdfs")
+    @mock.patch("documents.tasks.consume_file.s")
+    def test_edit_pdf_maps_operations_to_outputs(
+        self,
+        mock_consume_file: mock.Mock,
+        mock_build_pdfs: mock.Mock,
+        mock_group: mock.Mock,
+    ) -> None:
+        """
+        GIVEN:
+            - Existing document
+        WHEN:
+            - edit_pdf is called with operations interleaved across two outputs,
+              some of them rotated
+        THEN:
+            - Each output is built from its own operations, in operation order,
+              with the requested rotation
+        """
+        mock_build_pdfs.return_value = [self.doc2.source_path, self.doc2.source_path]
+        mock_group.return_value.delay.return_value = None
+        operations = [
+            {"page": 3, "doc": 1},
+            {"page": 1, "doc": 0, "rotate": 90},
+            {"page": 2, "doc": 1, "rotate": 180},
+        ]
+
+        bulk_edit.edit_pdf([self.doc2.id], operations)
+
+        outputs = mock_build_pdfs.call_args.args[1]
+        self.assertEqual(
+            [specs for specs, _ in outputs],
+            [[PageSpec(1, 90)], [PageSpec(3), PageSpec(2, 180)]],
+        )
+
     @mock.patch("documents.bulk_edit.group")
     @mock.patch("documents.tasks.consume_file.s")
     def test_edit_pdf_with_user_override(self, mock_consume_file, mock_group) -> None:
@@ -1534,12 +1570,10 @@ class TestPDFActions(DirectoriesMixin, TestCase):
 
     @mock.patch("documents.data_models.magic.from_file", return_value="application/pdf")
     @mock.patch("documents.tasks.consume_file.apply_async")
-    @mock.patch("pikepdf.new")
+    @mock.patch("documents.pdf_ops.build_pdfs")
-    @mock.patch("pikepdf.open")
     def test_edit_pdf_explicit_selection_uses_root_source_when_root_selected(
         self,
-        mock_open,
+        mock_build_pdfs,
-        mock_new,
         mock_consume_delay,
         mock_magic,
     ) -> None:
@@ -1548,12 +1582,7 @@ class TestPDFActions(DirectoriesMixin, TestCase):
             title="B version 1",
             root_document=self.doc2,
         )
-        fake_pdf = mock.MagicMock()
+        mock_build_pdfs.return_value = [Path("edited.pdf")]
-        fake_pdf.pages = [mock.Mock()]
-        mock_open.return_value.__enter__.return_value = fake_pdf
-        output_pdf = mock.MagicMock()
-        output_pdf.pages = []
-        mock_new.return_value = output_pdf
 
         result = bulk_edit.edit_pdf(
             [self.doc2.id],
@@ -1563,7 +1592,7 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
         self.assertEqual(result, "OK")
-        mock_open.assert_called_once_with(self.doc2.source_path)
+        self.assertEqual(mock_build_pdfs.call_args.args[0], self.doc2.source_path)
         mock_consume_delay.assert_called_once()
 
     @mock.patch("documents.bulk_edit.group")
@@ -1589,31 +1618,6 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         self.assertEqual(result, "OK")
         mock_group.return_value.delay.assert_called_once()
 
-    @mock.patch("documents.bulk_edit.group")
-    @mock.patch("documents.tasks.consume_file.s")
-    def test_edit_pdf_open_failure(
-        self,
-        mock_consume_file: mock.Mock,
-        mock_group: mock.Mock,
-    ) -> None:
-        """
-        GIVEN:
-            - Existing document
-        WHEN:
-            - edit_pdf fails to open PDF
-        THEN:
-            - Task group is not called
-        """
-        doc_ids = [self.doc2.id]
-        operations = [
-            {"page": 9999},  # invalid page, forces error during PDF load
-        ]
-        with self.assertLogs("paperless.bulk_edit", level="ERROR"):
-            with self.assertRaises(Exception):
-                bulk_edit.edit_pdf(doc_ids, operations)
-        mock_group.assert_not_called()
-        mock_consume_file.assert_not_called()
-
     @mock.patch("documents.bulk_edit.group")
     @mock.patch("documents.tasks.consume_file.s")
     def test_edit_pdf_multiple_outputs_with_update_flag_errors(
@@ -1640,23 +1644,15 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         mock_group.assert_not_called()
         mock_consume_file.assert_not_called()
 
-    @mock.patch("pikepdf.open")
-    def test_edit_pdf_rejects_invalid_operations(self, mock_open) -> None:
-        for operations in ([], [{"page": 1, "doc": 2**32}]):
-            with self.subTest(operations=operations):
-                with self.assertLogs("paperless.bulk_edit", level="ERROR"):
-                    with self.assertRaisesRegex(ValueError, "index is out of bounds"):
-                        bulk_edit.edit_pdf([self.doc2.id], operations)
-
-        mock_open.assert_not_called()
-
     @mock.patch("documents.bulk_edit.update_document_content_maybe_archive_file.delay")
     @mock.patch("documents.tasks.consume_file.apply_async")
     @mock.patch("documents.bulk_edit.tempfile.mkdtemp")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.decrypt_pdf")
+    @mock.patch("documents.pdf_ops.needs_decrypt", return_value=True)
     def test_remove_password_update_document(
         self,
-        mock_open,
+        mock_needs_decrypt,
+        mock_decrypt,
         mock_mkdtemp,
         mock_consume_delay,
         mock_update_document,
@@ -1665,16 +1661,7 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         temp_dir = self.dirs.scratch_dir / "remove-password-update"
         temp_dir.mkdir(parents=True, exist_ok=True)
         mock_mkdtemp.return_value = str(temp_dir)
-
+        mock_decrypt.side_effect = self.fake_decrypt
-        fake_pdf = mock.MagicMock()
-        fake_pdf.pages = [mock.Mock(), mock.Mock(), mock.Mock()]
-        fake_pdf.is_encrypted = True
-
-        def save_side_effect(target_path):
-            Path(target_path).write_bytes(b"new pdf content")
-
-        fake_pdf.save.side_effect = save_side_effect
-        mock_open.return_value.__enter__.return_value = fake_pdf
 
         result = bulk_edit.remove_password(
             [doc.id],
@@ -1683,14 +1670,8 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
         self.assertEqual(result, "OK")
-        self.assertEqual(
+        mock_needs_decrypt.assert_called_once_with(doc.source_path)
-            mock_open.call_args_list,
+        mock_decrypt.assert_called_once_with(doc.source_path, mock.ANY, "secret")
-            [
-                mock.call(doc.source_path),
-                mock.call(doc.source_path, password="secret"),
-            ],
-        )
-        fake_pdf.remove_unreferenced_resources.assert_called_once()
         mock_update_document.assert_not_called()
         mock_consume_delay.assert_called_once()
         task_kwargs = mock_consume_delay.call_args.kwargs["kwargs"]
@@ -1703,40 +1684,15 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         self.assertEqual(task_kwargs["input_doc"].root_document_id, doc.id)
         self.assertIsNotNone(task_kwargs["overrides"])
 
-    @mock.patch("documents.tasks.consume_file.apply_async")
-    @mock.patch("documents.bulk_edit.tempfile.mkdtemp")
-    @mock.patch("pikepdf.open")
-    def test_remove_password_update_document_skips_unencrypted_pdf(
-        self,
-        mock_open,
-        mock_mkdtemp,
-        mock_consume_delay,
-    ) -> None:
-        doc = self.doc1
-        fake_pdf = mock.MagicMock()
-        fake_pdf.is_encrypted = False
-        mock_open.return_value.__enter__.return_value = fake_pdf
-
-        result = bulk_edit.remove_password(
-            [doc.id],
-            password="secret",
-            update_document=True,
-        )
-
-        self.assertEqual(result, "OK")
-        mock_open.assert_called_once_with(doc.source_path)
-        fake_pdf.remove_unreferenced_resources.assert_not_called()
-        fake_pdf.save.assert_not_called()
-        mock_mkdtemp.assert_not_called()
-        mock_consume_delay.assert_not_called()
-
     @mock.patch("documents.bulk_edit.update_document_content_maybe_archive_file.delay")
     @mock.patch("documents.tasks.consume_file.apply_async")
     @mock.patch("documents.bulk_edit.tempfile.mkdtemp")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.decrypt_pdf")
+    @mock.patch("documents.pdf_ops.needs_decrypt", return_value=True)
     def test_remove_password_update_document_uses_source_paths(
         self,
-        mock_open,
+        mock_needs_decrypt,
+        mock_decrypt,
         mock_mkdtemp,
         mock_consume_delay,
         mock_update_document,
@@ -1747,14 +1703,7 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         temp_dir = self.dirs.scratch_dir / "remove-password-source-file"
         temp_dir.mkdir(parents=True, exist_ok=True)
         mock_mkdtemp.return_value = str(temp_dir)
-
+        mock_decrypt.side_effect = self.fake_decrypt
-        fake_pdf = mock.MagicMock()
-        self.mock_password_required_pdf(mock_open, fake_pdf)
-
-        def save_side_effect(target_path):
-            Path(target_path).write_bytes(b"new pdf content")
-
-        fake_pdf.save.side_effect = save_side_effect
 
         result = bulk_edit.remove_password(
             [doc.id],
@@ -1764,22 +1713,19 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
         self.assertEqual(result, "OK")
-        self.assertEqual(
+        mock_needs_decrypt.assert_called_once_with(source_file)
-            mock_open.call_args_list,
+        mock_decrypt.assert_called_once_with(source_file, mock.ANY, "secret")
-            [
-                mock.call(source_file),
-                mock.call(source_file, password="secret"),
-            ],
-        )
         mock_update_document.assert_not_called()
         mock_consume_delay.assert_called_once()
 
     @mock.patch("documents.data_models.magic.from_file", return_value="application/pdf")
     @mock.patch("documents.tasks.consume_file.apply_async")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.decrypt_pdf")
+    @mock.patch("documents.pdf_ops.needs_decrypt", return_value=True)
     def test_remove_password_explicit_selection_uses_root_source_when_root_selected(
         self,
-        mock_open,
+        mock_needs_decrypt,
+        mock_decrypt,
         mock_consume_delay,
         mock_magic,
     ) -> None:
@@ -1788,8 +1734,7 @@ class TestPDFActions(DirectoriesMixin, TestCase):
             title="A version 1",
             root_document=self.doc1,
         )
-        fake_pdf = mock.MagicMock()
+        mock_decrypt.return_value = Path("unprotected.pdf")
-        self.mock_password_required_pdf(mock_open, fake_pdf)
 
         result = bulk_edit.remove_password(
             [self.doc1.id],
@@ -1799,12 +1744,11 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
         self.assertEqual(result, "OK")
-        self.assertEqual(
+        mock_needs_decrypt.assert_called_once_with(self.doc1.source_path)
-            mock_open.call_args_list,
+        mock_decrypt.assert_called_once_with(
-            [
+            self.doc1.source_path,
-                mock.call(self.doc1.source_path),
+            mock.ANY,
-                mock.call(self.doc1.source_path, password="secret"),
+            "secret",
-            ],
         )
         mock_consume_delay.assert_called_once()
 
@@ -1812,10 +1756,12 @@ class TestPDFActions(DirectoriesMixin, TestCase):
     @mock.patch("documents.bulk_edit.group")
     @mock.patch("documents.tasks.consume_file.s")
     @mock.patch("documents.bulk_edit.tempfile.mkdtemp")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.decrypt_pdf")
+    @mock.patch("documents.pdf_ops.needs_decrypt", return_value=True)
     def test_remove_password_creates_consumable_document(
         self,
-        mock_open: mock.Mock,
+        mock_needs_decrypt: mock.Mock,
+        mock_decrypt: mock.Mock,
         mock_mkdtemp: mock.Mock,
         mock_consume_file: mock.Mock,
         mock_group: mock.Mock,
@@ -1825,15 +1771,7 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         temp_dir = self.dirs.scratch_dir / "remove-password"
         temp_dir.mkdir(parents=True, exist_ok=True)
         mock_mkdtemp.return_value = str(temp_dir)
-
+        mock_decrypt.side_effect = self.fake_decrypt
-        fake_pdf = mock.MagicMock()
-        fake_pdf.pages = [mock.Mock(), mock.Mock()]
-        self.mock_password_required_pdf(mock_open, fake_pdf)
-
-        def save_side_effect(target_path: Path) -> None:
-            target_path.write_bytes(b"password removed")
-
-        fake_pdf.save.side_effect = save_side_effect
         mock_group.return_value.delay.return_value = None
 
         user = User.objects.create(username="owner")
@@ -1848,13 +1786,7 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
         self.assertEqual(result, "OK")
-        self.assertEqual(
+        mock_decrypt.assert_called_once_with(doc.source_path, mock.ANY, "secret")
-            mock_open.call_args_list,
-            [
-                mock.call(doc.source_path),
-                mock.call(doc.source_path, password="secret"),
-            ],
-        )
         mock_consume_file.assert_called_once()
         call_kwargs = mock_consume_file.call_args.kwargs
         consumable_document = call_kwargs["input_doc"]
@@ -1876,21 +1808,18 @@ class TestPDFActions(DirectoriesMixin, TestCase):
     @mock.patch("documents.bulk_edit.chord")
     @mock.patch("documents.bulk_edit.group")
     @mock.patch("documents.tasks.consume_file.s")
-    @mock.patch("documents.bulk_edit.tempfile.mkdtemp")
+    @mock.patch("documents.pdf_ops.decrypt_pdf")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.needs_decrypt", return_value=False)
     def test_remove_password_skips_unencrypted_pdf_without_queueing(
         self,
-        mock_open: mock.Mock,
+        mock_needs_decrypt: mock.Mock,
-        mock_mkdtemp: mock.Mock,
+        mock_decrypt: mock.Mock,
         mock_consume_file: mock.Mock,
         mock_group: mock.Mock,
         mock_chord: mock.Mock,
         mock_delete: mock.Mock,
     ) -> None:
         doc = self.doc2
-        fake_pdf = mock.MagicMock()
-        fake_pdf.is_encrypted = False
-        mock_open.return_value.__enter__.return_value = fake_pdf
 
         result = bulk_edit.remove_password(
             [doc.id],
@@ -1900,10 +1829,8 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
         self.assertEqual(result, "OK")
-        mock_open.assert_called_once_with(doc.source_path)
+        mock_needs_decrypt.assert_called_once_with(doc.source_path)
-        fake_pdf.remove_unreferenced_resources.assert_not_called()
+        mock_decrypt.assert_not_called()
-        fake_pdf.save.assert_not_called()
-        mock_mkdtemp.assert_not_called()
         mock_consume_file.assert_not_called()
         mock_group.assert_not_called()
         mock_chord.assert_not_called()
@@ -1914,10 +1841,12 @@ class TestPDFActions(DirectoriesMixin, TestCase):
     @mock.patch("documents.bulk_edit.group")
     @mock.patch("documents.tasks.consume_file.s")
     @mock.patch("documents.bulk_edit.tempfile.mkdtemp")
-    @mock.patch("pikepdf.open")
+    @mock.patch("documents.pdf_ops.decrypt_pdf")
+    @mock.patch("documents.pdf_ops.needs_decrypt", return_value=True)
     def test_remove_password_deletes_original(
         self,
-        mock_open: mock.Mock,
+        mock_needs_decrypt: mock.Mock,
+        mock_decrypt: mock.Mock,
         mock_mkdtemp: mock.Mock,
         mock_consume_file: mock.Mock,
         mock_group: mock.Mock,
@@ -1928,15 +1857,7 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         temp_dir = self.dirs.scratch_dir / "remove-password-delete"
         temp_dir.mkdir(parents=True, exist_ok=True)
         mock_mkdtemp.return_value = str(temp_dir)
-
+        mock_decrypt.side_effect = self.fake_decrypt
-        fake_pdf = mock.MagicMock()
-        fake_pdf.pages = [mock.Mock(), mock.Mock()]
-        self.mock_password_required_pdf(mock_open, fake_pdf)
-
-        def save_side_effect(target_path: Path) -> None:
-            target_path.write_bytes(b"password removed")
-
-        fake_pdf.save.side_effect = save_side_effect
         mock_chord.return_value.delay.return_value = None
 
         result = bulk_edit.remove_password(
@@ -1948,23 +1869,23 @@ class TestPDFActions(DirectoriesMixin, TestCase):
         )
 
         self.assertEqual(result, "OK")
-        self.assertEqual(
+        mock_decrypt.assert_called_once_with(doc.source_path, mock.ANY, "secret")
-            mock_open.call_args_list,
-            [
-                mock.call(doc.source_path),
-                mock.call(doc.source_path, password="secret"),
-            ],
-        )
         mock_consume_file.assert_called_once()
         mock_group.assert_not_called()
         mock_chord.assert_called_once()
         mock_chord.return_value.delay.assert_called_once()
         mock_delete.si.assert_called_once_with([doc.id])
 
-    @mock.patch("pikepdf.open")
+    @mock.patch(
-    def test_remove_password_open_failure(self, mock_open: mock.Mock) -> None:
+        "documents.pdf_ops.decrypt_pdf",
-        mock_open.side_effect = RuntimeError("wrong password")
+        side_effect=RuntimeError("wrong password"),
-
+    )
+    @mock.patch("documents.pdf_ops.needs_decrypt", return_value=True)
+    def test_remove_password_failure_raises_value_error(
+        self,
+        mock_needs_decrypt: mock.Mock,
+        mock_decrypt: mock.Mock,
+    ) -> None:
         with self.assertLogs("paperless.bulk_edit", level="ERROR") as cm:
             with self.assertRaises(ValueError) as exc:
                 bulk_edit.remove_password([self.doc1.id], password="secret")

src/documents/tests/test_management_exporter.py

@@ -2,6 +2,7 @@ import hashlib
 import json
 import shutil
 import tempfile
+from datetime import date
 from datetime import timedelta
 from io import StringIO
 from pathlib import Path
@@ -44,14 +45,18 @@ from documents.models import Workflow
 from documents.models import WorkflowAction
 from documents.models import WorkflowTrigger
 from documents.sanity_checker import check_sanity
+from documents.settings import EXPORTER_ARCHIVE_NAME
 from documents.settings import EXPORTER_FILE_NAME
 from documents.settings import EXPORTER_SHARE_LINK_BUNDLE_NAME
+from documents.settings import EXPORTER_THUMBNAIL_NAME
 from documents.tests.utils import SampleDirMixin
 from paperless_mail.models import MailAccount
 from paperless_testing.assertions import FileSystemAssertsMixin
 from paperless_testing.dirs import DirectoriesMixin
+from paperless_testing.dirs import PaperlessDirs
 from paperless_testing.dirs import paperless_environment
 from paperless_testing.factories import DocumentBarcodeFactory
+from paperless_testing.factories import DocumentFactory
 from paperless_testing.permissions import grant_object
 
 
@@ -1462,3 +1467,73 @@ class TestCryptExportImport(
             ("No passphrase was given, sensitive fields will be in plaintext"),
             stdout.read(),
         )
+
+
+@pytest.mark.management
+@pytest.mark.django_db
+class TestExportDerivedFileNameCollisions:
+    def test_same_stem_different_extension_get_distinct_derived_files(
+        self,
+        paperless_dirs: PaperlessDirs,
+        tmp_path: Path,
+    ) -> None:
+        """
+        GIVEN:
+            - Two documents with the same title and created date
+            - One original is a PDF, the other a PNG, both with archive and thumbnail
+        WHEN:
+            - The exporter runs
+        THEN:
+            - Each document is exported under a distinct original, thumbnail and archive name
+            - Each exported file holds its own document's content
+        """
+        for pk, (filename, mime_type) in enumerate(
+            [("collide.pdf", "application/pdf"), ("collide.png", "image/png")],
+            start=1,
+        ):
+            (paperless_dirs.originals_dir / filename).write_bytes(
+                f"original {pk}".encode(),
+            )
+            (paperless_dirs.archive_dir / f"{pk:07}.pdf").write_bytes(
+                f"archive {pk}".encode(),
+            )
+            (paperless_dirs.thumbnail_dir / f"{pk:07}.webp").write_bytes(
+                f"thumbnail {pk}".encode(),
+            )
+            DocumentFactory(
+                pk=pk,
+                title="collide",
+                created=date(2026, 10, 7),
+                filename=filename,
+                archive_filename=f"{pk:07}.pdf",
+                mime_type=mime_type,
+            )
+
+        target = tmp_path / "export"
+        target.mkdir()
+        call_command(
+            "document_exporter",
+            str(target),
+            "--no-progress-bar",
+            skip_checks=True,
+        )
+
+        manifest = json.loads((target / "manifest.json").read_text())
+        records = {r["pk"]: r for r in manifest if r["model"] == "documents.document"}
+
+        for key in (
+            EXPORTER_FILE_NAME,
+            EXPORTER_THUMBNAIL_NAME,
+            EXPORTER_ARCHIVE_NAME,
+        ):
+            assert records[1][key] != records[2][key]
+
+        for pk in (1, 2):
+            record = records[pk]
+            assert (target / record[EXPORTER_FILE_NAME]).read_text() == f"original {pk}"
+            assert (
+                target / record[EXPORTER_THUMBNAIL_NAME]
+            ).read_text() == f"thumbnail {pk}"
+            assert (
+                target / record[EXPORTER_ARCHIVE_NAME]
+            ).read_text() == f"archive {pk}"

src/documents/tests/test_pdf_ops.py

@@ -0,0 +1,520 @@
+"""
+Tests for documents.pdf_ops.
+
+These use real PDFs from the sample directories. No database, Celery or mocks.
+Pages are compared by a hash of their content stream, so page identity and order
+are easy to assert.
+"""
+
+import hashlib
+from collections.abc import Callable
+from pathlib import Path
+
+import pikepdf
+import pytest
+
+from documents import pdf_ops
+from documents.pdf_ops import PageSpec
+
+SRC_ROOT = Path(__file__).parents[2]
+SAMPLES = Path(__file__).parent / "samples"
+THREE_PAGES = SAMPLES / "documents" / "originals" / "0000002.pdf"
+TWELVE_PAGES = SAMPLES / "barcodes" / "split-by-asn-2.pdf"
+ENCRYPTED = SAMPLES / "password-is-test.pdf"
+SIGNED = SRC_ROOT / "paperless" / "tests" / "samples" / "tesseract" / "signed.pdf"
+
+
+def _page_fingerprint(page: pikepdf.Page) -> str:
+    contents = page.obj.get("/Contents")
+    assert contents is not None, "sample page has no /Contents"
+    streams = list(contents) if isinstance(contents, pikepdf.Array) else [contents]
+    return hashlib.sha256(b"".join(s.read_bytes() for s in streams)).hexdigest()
+
+
+def fingerprints(path: Path) -> list[str]:
+    with pikepdf.open(path) as pdf:
+        return [_page_fingerprint(page) for page in pdf.pages]
+
+
+def rotations(path: Path) -> list[int]:
+    with pikepdf.open(path) as pdf:
+        return [int(page.obj.get("/Rotate", 0)) for page in pdf.pages]
+
+
+def docinfo_keys(path: Path) -> set[str]:
+    with pikepdf.open(path) as pdf:
+        return set(pdf.docinfo.keys())
+
+
+def constant(path: Path) -> Callable[[], Path]:
+    return lambda: path
+
+
+@pytest.fixture
+def source_fingerprints() -> list[str]:
+    fps = fingerprints(THREE_PAGES)
+    assert len(set(fps)) == 3, "sample must have three distinct pages"
+    return fps
+
+
+class TestRotatePdf:
+    def test_rotation_is_relative_and_applies_to_every_page(
+        self,
+        tmp_path: Path,
+    ) -> None:
+        """
+        GIVEN:
+            - A three page PDF
+        WHEN:
+            - It is rotated by 90 degrees, then the result is rotated by 90 again
+        THEN:
+            - Every page is rotated relative to its current rotation
+            - The page content itself is unchanged
+        """
+        once = tmp_path / "once.pdf"
+        twice = tmp_path / "twice.pdf"
+
+        pdf_ops.rotate_pdf(THREE_PAGES, once, 90)
+        pdf_ops.rotate_pdf(once, twice, 90)
+
+        assert rotations(once) == [90, 90, 90]
+        assert rotations(twice) == [180, 180, 180]
+        assert fingerprints(twice) == fingerprints(THREE_PAGES)
+
+    def test_keeps_document_info(self, tmp_path: Path) -> None:
+        """
+        GIVEN:
+            - A PDF with document info
+        WHEN:
+            - It is rotated
+        THEN:
+            - The document info is still present in the output
+        """
+        dst = tmp_path / "out.pdf"
+
+        pdf_ops.rotate_pdf(THREE_PAGES, dst, 90)
+
+        assert "/Creator" in docinfo_keys(dst)
+
+
+class TestRemovePages:
+    @pytest.mark.parametrize(
+        ("pages", "kept"),
+        [
+            pytest.param([2], [0, 2], id="single"),
+            pytest.param([3, 1], [1], id="unordered"),
+            pytest.param([2, 2], [0, 2], id="duplicates-remove-once"),
+            pytest.param([], [0, 1, 2], id="empty-keeps-everything"),
+            pytest.param([1, 2, 3], [], id="every-page"),
+        ],
+    )
+    def test_removes_only_the_requested_pages(
+        self,
+        tmp_path: Path,
+        source_fingerprints: list[str],
+        pages: list[int],
+        kept: list[int],
+    ) -> None:
+        """
+        GIVEN:
+            - A three page PDF
+        WHEN:
+            - Pages are removed, in any order and possibly repeated
+        THEN:
+            - Exactly the other pages remain, in their original order
+        """
+        dst = tmp_path / "out.pdf"
+
+        pdf_ops.remove_pages(THREE_PAGES, dst, pages)
+
+        assert fingerprints(dst) == [source_fingerprints[i] for i in kept]
+
+    def test_keeps_document_info(self, tmp_path: Path) -> None:
+        """
+        GIVEN:
+            - A PDF with document info
+        WHEN:
+            - A page is removed
+        THEN:
+            - The document info is still present in the output
+        """
+        dst = tmp_path / "out.pdf"
+
+        pdf_ops.remove_pages(THREE_PAGES, dst, [1])
+
+        assert "/Creator" in docinfo_keys(dst)
+
+    @pytest.mark.parametrize(
+        "bad_page",
+        [
+            pytest.param(0, id="zero"),
+            pytest.param(-1, id="negative"),
+        ],
+    )
+    def test_rejects_pages_below_one(self, tmp_path: Path, bad_page: int) -> None:
+        """
+        GIVEN:
+            - A three page PDF
+        WHEN:
+            - Pages are removed and one of them is below 1
+        THEN:
+            - ValueError is raised
+            - No output file is written
+        """
+        dst = tmp_path / "out.pdf"
+
+        with pytest.raises(ValueError, match="start at 1"):
+            pdf_ops.remove_pages(THREE_PAGES, dst, [1, bad_page])
+
+        assert not dst.exists()
+
+
+class TestBuildPdfs:
+    def test_selects_and_orders_pages(
+        self,
+        tmp_path: Path,
+        source_fingerprints: list[str],
+    ) -> None:
+        """
+        GIVEN:
+            - A three page PDF
+        WHEN:
+            - One output is built from pages 3 then 1
+        THEN:
+            - The output has those pages in that order
+            - Its path is returned
+        """
+        dst = tmp_path / "out.pdf"
+
+        written = pdf_ops.build_pdfs(
+            THREE_PAGES,
+            [([PageSpec(3), PageSpec(1)], constant(dst))],
+        )
+
+        assert written == [dst]
+        assert fingerprints(dst) == [source_fingerprints[2], source_fingerprints[0]]
+
+    def test_rotates_only_the_requested_pages(self, tmp_path: Path) -> None:
+        """
+        GIVEN:
+            - A three page PDF
+        WHEN:
+            - One output is built with a different rotation on each page
+        THEN:
+            - Each output page has exactly the rotation requested for it
+        """
+        dst = tmp_path / "out.pdf"
+
+        pdf_ops.build_pdfs(
+            THREE_PAGES,
+            [([PageSpec(1), PageSpec(2, 90), PageSpec(3, 180)], constant(dst))],
+        )
+
+        assert rotations(dst) == [0, 90, 180]
+
+    def test_writes_one_file_per_output_in_order(self, tmp_path: Path) -> None:
+        """
+        GIVEN:
+            - A twelve page PDF
+        WHEN:
+            - Two outputs are built from different page ranges
+        THEN:
+            - Two files are written and returned in output order
+            - Each holds exactly its own pages
+        """
+        first = tmp_path / "first.pdf"
+        second = tmp_path / "second.pdf"
+        source = fingerprints(TWELVE_PAGES)
+
+        written = pdf_ops.build_pdfs(
+            TWELVE_PAGES,
+            [
+                ([PageSpec(p) for p in (1, 2, 3)], constant(first)),
+                ([PageSpec(p) for p in range(4, 13)], constant(second)),
+            ],
+        )
+
+        assert written == [first, second]
+        assert fingerprints(first) == source[:3]
+        assert fingerprints(second) == source[3:]
+
+    def test_empty_page_list_writes_a_zero_page_file(self, tmp_path: Path) -> None:
+        """
+        GIVEN:
+            - A three page PDF
+        WHEN:
+            - An output with no pages is built
+        THEN:
+            - A PDF with zero pages is written
+        """
+        dst = tmp_path / "out.pdf"
+
+        pdf_ops.build_pdfs(THREE_PAGES, [([], constant(dst))])
+
+        assert fingerprints(dst) == []
+
+    def test_destination_is_not_requested_when_a_page_is_out_of_range(
+        self,
+        tmp_path: Path,
+    ) -> None:
+        """
+        GIVEN:
+            - A three page PDF
+        WHEN:
+            - Several outputs are built
+            - A later output refers to a page past the end
+        THEN:
+            - IndexError is raised
+            - No destination was requested for any output, including earlier valid ones
+        """
+        requested: list[Path] = []
+
+        def make_dst() -> Path:
+            requested.append(tmp_path / "out.pdf")
+            return requested[-1]
+
+        with pytest.raises(IndexError):
+            pdf_ops.build_pdfs(
+                THREE_PAGES,
+                [([PageSpec(1)], make_dst), ([PageSpec(99)], make_dst)],
+            )
+
+        assert requested == []
+
+    @pytest.mark.parametrize(
+        "bad_page",
+        [
+            pytest.param(0, id="zero"),
+            pytest.param(-1, id="negative"),
+        ],
+    )
+    def test_rejects_pages_below_one_before_opening_anything(
+        self,
+        tmp_path: Path,
+        bad_page: int,
+    ) -> None:
+        """
+        GIVEN:
+            - A three page PDF
+        WHEN:
+            - Several outputs are built and a later one has a page below 1
+        THEN:
+            - ValueError is raised
+            - No destination was requested for any output
+        """
+        requested: list[Path] = []
+
+        def make_dst() -> Path:
+            requested.append(tmp_path / "out.pdf")
+            return requested[-1]
+
+        with pytest.raises(ValueError, match="start at 1"):
+            pdf_ops.build_pdfs(
+                THREE_PAGES,
+                [([PageSpec(1)], make_dst), ([PageSpec(bad_page)], make_dst)],
+            )
+
+        assert requested == []
+
+
+class TestValidatePageOperations:
+    def test_returns_the_output_count(self) -> None:
+        """
+        GIVEN:
+            - Operations that all target the default output
+        WHEN:
+            - They are validated
+        THEN:
+            - One output document is reported
+        """
+        operations = [{"page": 1}, {"page": 2}, {"page": 3}]
+
+        assert pdf_ops.validate_page_operations(operations, single_output=True) == 1
+
+    def test_gap_in_output_indices_counts_up_to_the_highest(self) -> None:
+        """
+        GIVEN:
+            - Operations that target outputs 0 and 2 but never 1
+        WHEN:
+            - They are validated
+        THEN:
+            - Three output documents are reported
+        """
+        operations = [
+            {"page": 1, "doc": 0},
+            {"page": 2, "doc": 2},
+            {"page": 3, "doc": 0},
+        ]
+
+        count = pdf_ops.validate_page_operations(operations, single_output=False)
+
+        assert count == 3
+
+    def test_empty_operations_are_rejected(self) -> None:
+        """
+        GIVEN:
+            - No operations
+        WHEN:
+            - They are validated
+        THEN:
+            - ValueError is raised
+        """
+        with pytest.raises(ValueError, match="index is out of bounds"):
+            pdf_ops.validate_page_operations([], single_output=False)
+
+    def test_multiple_outputs_rejected_when_single_output_required(self) -> None:
+        """
+        GIVEN:
+            - Operations that target two outputs
+        WHEN:
+            - They are validated with a single output required
+        THEN:
+            - ValueError is raised
+        """
+        operations = [{"page": 1, "doc": 0}, {"page": 2, "doc": 1}]
+
+        with pytest.raises(ValueError, match="Multiple output documents"):
+            pdf_ops.validate_page_operations(operations, single_output=True)
+
+    @pytest.mark.parametrize(
+        "doc",
+        [
+            pytest.param(-1, id="negative"),
+            pytest.param(2, id="equal-to-operation-count"),
+            pytest.param(2**32, id="huge"),
+        ],
+    )
+    def test_output_index_out_of_bounds(self, doc: int) -> None:
+        """
+        GIVEN:
+            - Two operations, one with an output index that is out of bounds
+        WHEN:
+            - They are validated
+        THEN:
+            - ValueError is raised
+        """
+        operations = [{"page": 1, "doc": 0}, {"page": 2, "doc": doc}]
+
+        with pytest.raises(ValueError, match="index is out of bounds"):
+            pdf_ops.validate_page_operations(operations, single_output=False)
+
+
+class TestDecrypt:
+    @pytest.mark.parametrize(
+        ("path", "expected"),
+        [
+            pytest.param(ENCRYPTED, True, id="password-required"),
+            pytest.param(SIGNED, True, id="opens-without-password-but-encrypted"),
+            pytest.param(THREE_PAGES, False, id="not-encrypted"),
+        ],
+    )
+    def test_needs_decrypt(self, path: Path, *, expected: bool) -> None:
+        """
+        GIVEN:
+            - A PDF that is encrypted, or encrypted but openable, or plain
+        WHEN:
+            - needs_decrypt is asked about it
+        THEN:
+            - Only the unencrypted PDF reports False
+        """
+        assert pdf_ops.needs_decrypt(path) is expected
+
+    def test_decrypt_writes_an_unencrypted_copy(self, tmp_path: Path) -> None:
+        """
+        GIVEN:
+            - A password protected PDF
+        WHEN:
+            - It is decrypted with the correct password
+        THEN:
+            - The path from make_dst is returned
+            - The written copy no longer needs decrypting
+        """
+        dst = tmp_path / "out.pdf"
+
+        result = pdf_ops.decrypt_pdf(ENCRYPTED, constant(dst), "test")
+
+        assert result == dst
+        assert pdf_ops.needs_decrypt(dst) is False
+
+    def test_wrong_password_raises_and_never_requests_a_destination(
+        self,
+        tmp_path: Path,
+    ) -> None:
+        """
+        GIVEN:
+            - A password protected PDF
+        WHEN:
+            - It is decrypted with the wrong password
+        THEN:
+            - PasswordError is raised
+            - No destination was requested
+        """
+        requested: list[Path] = []
+
+        def make_dst() -> Path:
+            requested.append(tmp_path / "out.pdf")
+            return requested[-1]
+
+        with pytest.raises(pikepdf.PasswordError):
+            pdf_ops.decrypt_pdf(ENCRYPTED, make_dst, "wrong")
+
+        assert requested == []
+
+
+class TestPdfMerger:
+    def test_pages_are_appended_in_the_order_added(
+        self,
+        tmp_path: Path,
+        source_fingerprints: list[str],
+    ) -> None:
+        """
+        GIVEN:
+            - A reordered PDF and the original three page PDF
+        WHEN:
+            - Both are added to a merger in that order and saved
+        THEN:
+            - The output holds all pages in the order they were added
+        """
+        reordered = tmp_path / "reordered.pdf"
+        merged = tmp_path / "merged.pdf"
+        pdf_ops.build_pdfs(
+            THREE_PAGES,
+            [([PageSpec(3), PageSpec(1)], constant(reordered))],
+        )
+
+        with pdf_ops.PdfMerger() as merger:
+            merger.add(reordered)
+            merger.add(THREE_PAGES)
+            merger.save(merged)
+
+        assert fingerprints(merged) == [
+            source_fingerprints[2],
+            source_fingerprints[0],
+            *source_fingerprints,
+        ]
+
+    def test_output_version_is_at_least_the_highest_source_version(
+        self,
+        tmp_path: Path,
+    ) -> None:
+        """
+        GIVEN:
+            - Two PDFs with different PDF versions
+        WHEN:
+            - Both are added to a merger and saved
+        THEN:
+            - The output version is at least the highest source version
+        """
+        merged = tmp_path / "merged.pdf"
+        with pikepdf.open(TWELVE_PAGES) as pdf:
+            source_versions = [pdf.pdf_version]
+        with pikepdf.open(THREE_PAGES) as pdf:
+            source_versions.append(pdf.pdf_version)
+
+        with pdf_ops.PdfMerger() as merger:
+            merger.add(TWELVE_PAGES)
+            merger.add(THREE_PAGES)
+            merger.save(merged)
+
+        with pikepdf.open(merged) as pdf:
+            assert pdf.pdf_version >= max(source_versions)