diff --git a/CHANGES/pulp_file/5686.bugfix b/CHANGES/pulp_file/5686.bugfix
new file mode 100644
index 00000000000..9b3605eb582
--- /dev/null
+++ b/CHANGES/pulp_file/5686.bugfix
@@ -0,0 +1 @@
+During sync, quote the URL path for file downloads using HTTP.
diff --git a/pulp_file/app/tasks/synchronizing.py b/pulp_file/app/tasks/synchronizing.py
index e7eaca0a235..705af7e282a 100644
--- a/pulp_file/app/tasks/synchronizing.py
+++ b/pulp_file/app/tasks/synchronizing.py
@@ -2,7 +2,7 @@
 import os
 
 from gettext import gettext as _
-from urllib.parse import urlparse, urlunparse
+from urllib.parse import quote, urlparse, urlunparse
 
 from django.core.files import File
 
@@ -113,7 +113,8 @@ async def run(self):
             await pb.asave()
 
             for entry in entries:
-                path = os.path.join(root_dir, entry.relative_path)
+                path = _get_safe_path(root_dir, entry, parsed_url.scheme)
+
                 url = urlunparse(parsed_url._replace(path=path))
                 file = FileContent(relative_path=entry.relative_path, digest=entry.digest)
                 artifact = Artifact(size=entry.size, sha256=entry.digest)
@@ -127,3 +128,9 @@ async def run(self):
                 dc = DeclarativeContent(content=file, d_artifacts=[da])
                 await pb.aincrement()
                 await self.put(dc)
+
+
+def _get_safe_path(root_dir, entry, scheme):
+    relative_path = entry.relative_path.lstrip("/")
+    path = os.path.join(root_dir, relative_path)
+    return path if scheme == "file" else quote(path, safe=":/")
diff --git a/pulp_file/tests/unit/test_safe_paths.py b/pulp_file/tests/unit/test_safe_paths.py
new file mode 100644
index 00000000000..36b05a20733
--- /dev/null
+++ b/pulp_file/tests/unit/test_safe_paths.py
@@ -0,0 +1,70 @@
+import pytest
+from unittest import mock
+from pulp_file.app.tasks.synchronizing import _get_safe_path
+
+
+@pytest.mark.parametrize(
+    "relative_path, scheme, expected_path",
+    [
+        # 1. Empty path
+        ("", "file", "/root/directory/"),
+        ("", "http", "/root/directory/"),
+        # 2. Leading/trailing slashes
+        ("/leading/slash.txt", "file", "/root/directory/leading/slash.txt"),
+        ("/leading/slash.txt", "http", "/root/directory/leading/slash.txt"),
+        ("trailing/slash.txt/", "file", "/root/directory/trailing/slash.txt/"),
+        ("trailing/slash.txt/", "http", "/root/directory/trailing/slash.txt/"),
+        # Special ASCII characters
+        ("file#name.txt", "file", "/root/directory/file#name.txt"),
+        ("file#name.txt", "http", "/root/directory/file%23name.txt"),
+        ("file?name.txt", "file", "/root/directory/file?name.txt"),
+        ("file?name.txt", "http", "/root/directory/file%3Fname.txt"),
+        ("file@name.txt", "file", "/root/directory/file@name.txt"),
+        ("file@name.txt", "http", "/root/directory/file%40name.txt"),
+        ("file$name.txt", "file", "/root/directory/file$name.txt"),
+        ("file$name.txt", "http", "/root/directory/file%24name.txt"),
+        ("file%name.txt", "file", "/root/directory/file%name.txt"),
+        ("file%name.txt", "http", "/root/directory/file%25name.txt"),
+        # Spaces
+        ("file  with  spaces.txt", "file", "/root/directory/file  with  spaces.txt"),
+        ("file  with  spaces.txt", "http", "/root/directory/file%20%20with%20%20spaces.txt"),
+        ("file.txt  ", "file", "/root/directory/file.txt  "),
+        ("file.txt  ", "http", "/root/directory/file.txt%20%20"),
+        # Unusual ASCII characters
+        ("file!name.txt", "file", "/root/directory/file!name.txt"),
+        ("file!name.txt", "http", "/root/directory/file%21name.txt"),
+        ("file'name.txt", "file", "/root/directory/file'name.txt"),
+        ("file'name.txt", "http", "/root/directory/file%27name.txt"),
+        ("file(name).txt", "file", "/root/directory/file(name).txt"),
+        ("file(name).txt", "http", "/root/directory/file%28name%29.txt"),
+        ("file[name].txt", "file", "/root/directory/file[name].txt"),
+        ("file[name].txt", "http", "/root/directory/file%5Bname%5D.txt"),
+        ("file;name.txt", "file", "/root/directory/file;name.txt"),
+        ("file;name.txt", "http", "/root/directory/file%3Bname.txt"),
+        ("file&name.txt", "file", "/root/directory/file&name.txt"),
+        ("file&name.txt", "http", "/root/directory/file%26name.txt"),
+        # Dots
+        (".", "file", "/root/directory/."),
+        (".", "http", "/root/directory/."),
+        ("..", "file", "/root/directory/.."),
+        ("..", "http", "/root/directory/.."),
+        # Mixed slashes
+        ("dir\\file.txt", "file", "/root/directory/dir\\file.txt"),
+        ("dir\\file.txt", "http", "/root/directory/dir%5Cfile.txt"),
+        ("///path//to///file.txt", "file", "/root/directory/path//to///file.txt"),
+        ("///path//to///file.txt", "http", "/root/directory/path//to///file.txt"),
+        # Only special characters
+        ("!@#$%^&*()", "file", "/root/directory/!@#$%^&*()"),
+        ("!@#$%^&*()", "http", "/root/directory/%21%40%23%24%25%5E%26%2A%28%29"),
+        # Encoded characters
+        ("file%3a.txt", "file", "/root/directory/file%3a.txt"),
+        ("file%3a.txt", "http", "/root/directory/file%253a.txt"),
+        ("file%3A.txt", "file", "/root/directory/file%3A.txt"),
+        ("file%3A.txt", "http", "/root/directory/file%253A.txt"),
+    ],
+)
+def test_get_safe_path(relative_path, scheme, expected_path):
+    entry = mock.Mock(relative_path=relative_path)
+    root_dir = "/root/directory"
+    result = _get_safe_path(root_dir, entry, scheme)
+    assert result == expected_path