diff --git a/src/paperless/network.py b/src/paperless/network.py
index 7c598063c..83d48e12d 100644
--- a/src/paperless/network.py
+++ b/src/paperless/network.py
@@ -1,5 +1,6 @@
 import functools
 import ipaddress
+import re
 import socket
 from collections.abc import Callable
 from collections.abc import Collection
@@ -207,6 +208,12 @@ def format_host_for_url(host: str) -> str:
         return host
 
 
+# urllib3 treats a backslash as ending the authority while urlparse and httpx do
+# not, so the host checked here could differ from the one that is dialled.
+# Control and whitespace characters are refused for the same reason.
+_UNSAFE_URL_CHARS = re.compile(r"[\\\x00-\x1f\x7f\s]")
+
+
 def _dns_name(url: str) -> str:
     """
     The ASCII hostname that httpx and urllib3 look up for ``url``.
@@ -246,6 +253,8 @@ def validate_outbound_http_url(
         raise ValueError("Destination port not permitted.")
 
     if not allow_internal:
+        if _UNSAFE_URL_CHARS.search(url):
+            raise ValueError("Invalid URL scheme or hostname.")
         try:
             resolve_public_addresses(_dns_name(url), port)
         except (OutboundRequestBlockedError, HostResolutionError) as e:
diff --git a/src/paperless/tests/test_network.py b/src/paperless/tests/test_network.py
index 09a35fe82..23d9fb3ba 100644
--- a/src/paperless/tests/test_network.py
+++ b/src/paperless/tests/test_network.py
@@ -590,3 +590,52 @@ class TestValidateOutboundHttpUrl:
             )
 
         resolver.assert_not_called()
+
+    @pytest.mark.parametrize(
+        "url",
+        [
+            pytest.param(r"http://127.0.0.1\@evil.example/", id="backslash"),
+            pytest.param(
+                r"http://127.0.0.1:80\@evil.example/",
+                id="backslash-with-port",
+            ),
+            pytest.param("http://evil\t.example/", id="tab-in-host"),
+            pytest.param("http://evil .example/", id="space-in-host"),
+        ],
+    )
+    def test_rejects_urls_http_clients_may_parse_differently(
+        self,
+        mocker: MockerFixture,
+        url: str,
+    ) -> None:
+        """
+        GIVEN:
+            - A URL containing a backslash, control or whitespace character,
+              which urllib3 may split into a different host than urlparse and
+              httpx do
+            - A resolver that would answer with a public address
+        WHEN:
+            - The URL is validated with internal addresses disallowed
+        THEN:
+            - It is rejected as invalid without a resolver call
+        """
+        resolver = _answer(mocker, "93.184.216.34")
+
+        with pytest.raises(ValueError, match="Invalid URL scheme or hostname"):
+            validate_outbound_http_url(url, allow_internal=False)
+
+        resolver.assert_not_called()
+
+    def test_allow_internal_does_not_reject_backslash(self) -> None:
+        """
+        GIVEN:
+            - A URL containing a backslash
+        WHEN:
+            - The URL is validated with internal addresses allowed
+        THEN:
+            - It is not rejected, since no host check is made
+        """
+        validate_outbound_http_url(
+            r"http://127.0.0.1\@evil.example/",
+            allow_internal=True,
+        )