diff --git a/Annex/Content.hs b/Annex/Content.hs
index 93d111140f..63746298d9 100644
--- a/Annex/Content.hs
+++ b/Annex/Content.hs
@@ -512,6 +512,12 @@ withTmp key action = do
 moveAnnex :: Key -> AssociatedFile -> RawFilePath -> Annex Bool
 moveAnnex key af src = ifM (checkSecureHashes' key)
 	( do
+#ifdef mingw32_HOST_OS
+		{- Windows prevents deletion of files that are not
+		 - writable, and the file could have such a mode.
+		 - So avoid problems with deleting the file, now or later. -}
+		void $ liftIO $ tryIO $ allowWrite src
+#endif
 		withObjectLoc key storeobject
 		return True
 	, return False
@@ -733,7 +739,11 @@ cleanObjectLoc key cleaner = do
 	 -}
 	whenM hasThawHook $
 		void $ tryIO $ thawContent file
-		
+#ifdef mingw32_HOST_OS
+	{- Windows prevents deletion of files that are not writable. -}
+	void $ liftIO $ tryIO $ allowWrite file
+#endif
+
 	cleaner
 	cleanObjectDirs file
 
diff --git a/CHANGELOG b/CHANGELOG
index 70c26b518b..b412a20602 100644
--- a/CHANGELOG
+++ b/CHANGELOG
@@ -9,6 +9,8 @@ git-annex (10.20250103) UNRELEASED; urgency=medium
   * Allow enableremote of an existing webdav special remote that has
     read-only access.
   * git-remote-annex: Use enableremote rather than initremote.
+  * Windows: Fix permission denied error when dropping files that
+    have the readonly attribute set.
 
  -- Joey Hess <id@joeyh.name>  Fri, 03 Jan 2025 14:30:38 -0400
 
diff --git a/doc/bugs/Fails_to_drop_key_on_windows___40__Access_denied__41__.mdwn b/doc/bugs/Fails_to_drop_key_on_windows___40__Access_denied__41__.mdwn
index 87a0c37e61..939c979a33 100644
--- a/doc/bugs/Fails_to_drop_key_on_windows___40__Access_denied__41__.mdwn
+++ b/doc/bugs/Fails_to_drop_key_on_windows___40__Access_denied__41__.mdwn
@@ -131,3 +131,5 @@ This observation comes from an effort to implement a git-remote-helper that uses
 
 [[!tag projects/datalad]]
 [[!tag projects/INM7]]
+
+> I think this is [[fixed|done]] now.. --[[Joey]]
diff --git a/doc/bugs/Fails_to_drop_key_on_windows___40__Access_denied__41__/comment_4_8a139e5a44ee9bae5195f46a7a67cfaf._comment b/doc/bugs/Fails_to_drop_key_on_windows___40__Access_denied__41__/comment_4_8a139e5a44ee9bae5195f46a7a67cfaf._comment
new file mode 100644
index 0000000000..08aa9e4831
--- /dev/null
+++ b/doc/bugs/Fails_to_drop_key_on_windows___40__Access_denied__41__/comment_4_8a139e5a44ee9bae5195f46a7a67cfaf._comment
@@ -0,0 +1,12 @@
+[[!comment format=mdwn
+ username="joey"
+ subject="""comment 4"""
+ date="2025-01-07T20:33:22Z"
+ content="""
+I see that the directory special remote, on windows, adds back the write
+permission on files before removing them. That was done way back in
+[[!commit 38022f4f493588505896635703c34afa6c2e2406]].
+
+I've applied the same fix now to the annex objects side, so this should be
+fixed.
+"""]]
diff --git a/doc/bugs/git-remote-annex_doesn__39__t_work_on_Windows___40__perms__41__.mdwn b/doc/bugs/git-remote-annex_doesn__39__t_work_on_Windows___40__perms__41__.mdwn
index 10a823cca6..8e38f1c17d 100644
--- a/doc/bugs/git-remote-annex_doesn__39__t_work_on_Windows___40__perms__41__.mdwn
+++ b/doc/bugs/git-remote-annex_doesn__39__t_work_on_Windows___40__perms__41__.mdwn
@@ -498,3 +498,5 @@ say I'm a believer. :)
 [[!meta author=jkniiv]]
 
 [[!tag projects/INM7]]
+
+> I think this is [[fixed|done]] --[[Joey]]
diff --git a/doc/bugs/git-remote-annex_doesn__39__t_work_on_Windows___40__perms__41__/comment_5_9a591141f1105490f359b58a3b29cd91._comment b/doc/bugs/git-remote-annex_doesn__39__t_work_on_Windows___40__perms__41__/comment_5_9a591141f1105490f359b58a3b29cd91._comment
new file mode 100644
index 0000000000..0b3b531fa7
--- /dev/null
+++ b/doc/bugs/git-remote-annex_doesn__39__t_work_on_Windows___40__perms__41__/comment_5_9a591141f1105490f359b58a3b29cd91._comment
@@ -0,0 +1,12 @@
+[[!comment format=mdwn
+ username="joey"
+ subject="""comment 5"""
+ date="2025-01-07T20:31:07Z"
+ content="""
+I see that the directory special remote, on windows, adds back the write
+permission on files before removing them. That was done way back in
+[[!commit 38022f4f493588505896635703c34afa6c2e2406]].
+
+I've applied the same fix now to the annex objects side, so this should be
+fixed.
+"""]]