diff --git a/beets/dbcore/db.py b/beets/dbcore/db.py
index 9d7469689..ca60f50ca 100755
--- a/beets/dbcore/db.py
+++ b/beets/dbcore/db.py
@@ -159,8 +159,8 @@ class FormattedMapping(Mapping[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 1ac16a8e2..6dbaa9e73 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -106,6 +106,9 @@ Bug fixes
   ``duplicate_action`` config options were silently ignored for as-is imports.
 - :doc:`/plugins/convert`: Fix extension substitution inside path of the
   exported playlist.
+- :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).
 
 For plugin developers
 ~~~~~~~~~~~~~~~~~~~~~