diff --git a/chrome/content/zotero/renameFiles.mjs b/chrome/content/zotero/renameFiles.mjs
index 9740a3c765..cedc0f1124 100644
--- a/chrome/content/zotero/renameFiles.mjs
+++ b/chrome/content/zotero/renameFiles.mjs
@@ -143,8 +143,9 @@ export async function renameFilesFromParent({ userLibrary = true, groupLibrary =
 				const oldBaseName = attachmentItem.attachmentFilename.replace(/\.[^.]+$/, '');
 				attachmentItem.attachmentFilename = newName;
 
-				// update title if it matches the old filename
-				if (attachmentItem.getField('title') === oldBaseName || attachmentItem.getField('title') === oldFileName) {
+				// update the title if it matches the old filename
+				const newTitleLC = attachmentItem.getField('title').toLowerCase();
+				if (newTitleLC === oldBaseName.toLowerCase() || newTitleLC === oldFileName.toLowerCase()) {
 					attachmentItem.setAutoAttachmentTitle({ ignoreAutoRenamePrefs: true });
 				}
 
@@ -164,7 +165,7 @@ export async function renameFilesFromParent({ userLibrary = true, groupLibrary =
 };
 
 /**
- * Renames an invidual attachment file based on its parent item's metadata.
+ * Renames an individual attachment file based on its parent item's metadata.
  *
  * @async
  * @param {Zotero.Item} attachmentItem - The attachment item to be renamed.
@@ -176,6 +177,7 @@ export async function renameFileFromParent(attachmentItem) {
 		throw new Error('Item ' + attachmentItem.itemID + ' cannot be renamed based on its parent item');
 	}
 
+	const oldName = attachmentItem.attachmentFilename;
 	const oldBaseName = attachmentItem.attachmentFilename.replace(/\.[^.]+$/, '');
 	const parentItemID = attachmentItem.parentItemID;
 	let parentItem = await Zotero.Items.getAsync(parentItemID);
@@ -187,12 +189,13 @@ export async function renameFileFromParent(attachmentItem) {
 
 	let requiresSave = false;
 	if (!renamed && attachmentItem.isStoredFileAttachment()) {
-		// file is not present locally but we can still update filename in the database
+		// the file is not present locally, but we can still update the filename in the database
 		attachmentItem.attachmentFilename = newName;
 		requiresSave = true;
 	}
-
-	if (attachmentItem.getField('title') === oldBaseName) {
+	
+	const newTitleLC = attachmentItem.getField('title').toLowerCase();
+	if (newTitleLC === oldBaseName.toLowerCase() || newTitleLC === oldName.toLowerCase()) {
 		attachmentItem.setAutoAttachmentTitle({ ignoreAutoRenamePrefs: true });
 		requiresSave = true;
 	}
diff --git a/test/tests/attachmentsTest.js b/test/tests/attachmentsTest.js
index ab1ae44d0d..d103ac52b7 100644
--- a/test/tests/attachmentsTest.js
+++ b/test/tests/attachmentsTest.js
@@ -2298,6 +2298,55 @@ describe("Zotero.Attachments", function () {
 			assert.equal(attachment.attachmentFilename, 'Title.png');
 			// After a manual rename, the title becomes the default for this type
 			assert.equal(attachment.getField('title'), Zotero.getString('file-type-image'));
+			
+		});
+
+		it("should change attachment title if file basename matches the title", async function () {
+			var item = createUnsavedDataObject('item');
+			item.setField('title', 'Title');
+			await item.saveTx();
+
+			var attachment = await importFileAttachment('test.pdf', {
+				parentItemID: item.id,
+				title: "test"
+			});
+			assert.equal(attachment.attachmentFilename, 'test.pdf');
+			assert.equal(attachment.getField('title'), 'test');
+			await renameFileFromParent(attachment);
+			assert.equal(attachment.attachmentFilename, 'Title.pdf');
+			assert.equal(attachment.getField('title'), Zotero.getString('file-type-pdf'));
+		});
+
+		it("should change attachment title if file matches the title exactly", async function () {
+			var item = createUnsavedDataObject('item');
+			item.setField('title', 'Title');
+			await item.saveTx();
+
+			var attachment = await importFileAttachment('test.pdf', {
+				parentItemID: item.id,
+				title: "test.pdf"
+			});
+			assert.equal(attachment.attachmentFilename, 'test.pdf');
+			assert.equal(attachment.getField('title'), 'test.pdf');
+			await renameFileFromParent(attachment);
+			assert.equal(attachment.attachmentFilename, 'Title.pdf');
+			assert.equal(attachment.getField('title'), Zotero.getString('file-type-pdf'));
+		});
+
+		it("should change attachment title if file matches the title, case-insensitive", async function () {
+			var item = createUnsavedDataObject('item');
+			item.setField('title', 'Title');
+			await item.saveTx();
+
+			var attachment = await importFileAttachment('test.pdf', {
+				parentItemID: item.id,
+				title: "tESt.PDF"
+			});
+			assert.equal(attachment.attachmentFilename, 'test.pdf');
+			assert.equal(attachment.getField('title'), 'tESt.PDF');
+			await renameFileFromParent(attachment);
+			assert.equal(attachment.attachmentFilename, 'Title.pdf');
+			assert.equal(attachment.getField('title'), Zotero.getString('file-type-pdf'));
 		});
 
 		it("should restore an extension when renaming a misnamed file", async function () {
@@ -2377,7 +2426,7 @@ describe("Zotero.Attachments", function () {
 			assert.equal(OS.Path.basename(path1), 'test.png');
 			assert.isTrue(await OS.File.exists(path1));
 
-			// pdf is the primary attachment, so renamed
+			// PDF is the primary attachment, so renamed
 			assert.equal(attachment2.attachmentFilename, 'Lorem.pdf');
 			let path2 = await attachment2.getFilePathAsync();
 			assert.equal(OS.Path.basename(path2), 'Lorem.pdf');