diff --git a/beets/dbcore/db.py b/beets/dbcore/db.py
index 9d7469689c..ca60f50caa 100755
--- a/beets/dbcore/db.py
+++ b/beets/dbcore/db.py
@@ -159,8 +159,8 @@ def _get_formatted(self, model: Model, key: str) -> str:
             sep_repl: str = beets.config["path_sep_replace"].as_str()
             sep_drive: str = beets.config["drive_sep_replace"].as_str()
 
-            if re.match(r"^\w:", value):
-                value = re.sub(r"(?<=^\w):", sep_drive, value)
+            if re.match(r"^[a-zA-Z]:", value):
+                value = re.sub(r"(?<=[a-zA-Z]):", sep_drive, value)
 
             for sep in (os.path.sep, os.path.altsep):
                 if sep:
diff --git a/docs/changelog.rst b/docs/changelog.rst
index 1ac16a8e27..4a944484f7 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -16,6 +16,9 @@ Unreleased
 Bug fixes
 ~~~~~~~~~
 
+- :ref:`replace`: Made ``drive_sep_replace`` regex logic more precise to prevent
+  edge-case mismatches (e.g., a song titled "1:00 AM" would incorrectly be
+  considered a Windows drive path).
 - :doc:`plugins/fish`: Fix AttributeError. :bug:`6340`
 
 ..