diff --git a/changelog.d/12244.misc b/changelog.d/12244.misc
new file mode 100644
index 000000000000..950d48e4c68e
--- /dev/null
+++ b/changelog.d/12244.misc
@@ -0,0 +1 @@
+Improve error message when dependencies check finds a broken installation.
\ No newline at end of file
diff --git a/synapse/util/check_dependencies.py b/synapse/util/check_dependencies.py
index 12cd8049392f..66f1da750289 100644
--- a/synapse/util/check_dependencies.py
+++ b/synapse/util/check_dependencies.py
@@ -128,6 +128,19 @@ def _incorrect_version(
         )
 
 
+def _no_reported_version(requirement: Requirement, extra: Optional[str] = None) -> str:
+    if extra:
+        return (
+            f"Synapse {VERSION} needs {requirement} for {extra}, "
+            f"but can't determine {requirement.name}'s version"
+        )
+    else:
+        return (
+            f"Synapse {VERSION} needs {requirement}, "
+            f"but can't determine {requirement.name}'s version"
+        )
+
+
 def check_requirements(extra: Optional[str] = None) -> None:
     """Check Synapse's dependencies are present and correctly versioned.
 
@@ -163,8 +176,17 @@ def check_requirements(extra: Optional[str] = None) -> None:
                 deps_unfulfilled.append(requirement.name)
                 errors.append(_not_installed(requirement, extra))
         else:
+            if dist.version is None:
+                # This shouldn't happen---it suggests a borked virtualenv. (See #12223)
+                # Try to give a vaguely helpful error message anyway.
+                # Type-ignore: the annotations don't reflect reality: see
+                #     https://github.com/python/typeshed/issues/7513
+                #     https://bugs.python.org/issue47060
+                deps_unfulfilled.append(requirement.name)  # type: ignore[unreachable]
+                errors.append(_no_reported_version(requirement, extra))
+
             # We specify prereleases=True to allow prereleases such as RCs.
-            if not requirement.specifier.contains(dist.version, prereleases=True):
+            elif not requirement.specifier.contains(dist.version, prereleases=True):
                 deps_unfulfilled.append(requirement.name)
                 errors.append(_incorrect_version(requirement, dist.version, extra))
 
diff --git a/tests/util/test_check_dependencies.py b/tests/util/test_check_dependencies.py
index 38e9f58ac6ca..5d1aa025d127 100644
--- a/tests/util/test_check_dependencies.py
+++ b/tests/util/test_check_dependencies.py
@@ -12,7 +12,7 @@
 
 
 class DummyDistribution(metadata.Distribution):
-    def __init__(self, version: str):
+    def __init__(self, version: object):
         self._version = version
 
     @property
@@ -30,6 +30,7 @@ def read_text(self, filename):
 old_release_candidate = DummyDistribution("0.1.2rc3")
 new = DummyDistribution("1.2.3")
 new_release_candidate = DummyDistribution("1.2.3rc4")
+distribution_with_no_version = DummyDistribution(None)
 
 # could probably use stdlib TestCase --- no need for twisted here
 
@@ -67,6 +68,18 @@ def test_mandatory_dependency(self) -> None:
                 # should not raise
                 check_requirements()
 
+    def test_version_reported_as_none(self) -> None:
+        """Complain if importlib.metadata.version() returns None.
+
+        This shouldn't normally happen, but it was seen in the wild (#12223).
+        """
+        with patch(
+            "synapse.util.check_dependencies.metadata.requires",
+            return_value=["dummypkg >= 1"],
+        ):
+            with self.mock_installed_package(distribution_with_no_version):
+                self.assertRaises(DependencyException, check_requirements)
+
     def test_checks_ignore_dev_dependencies(self) -> None:
         """Bot generic and per-extra checks should ignore dev dependencies."""
         with patch(