diff --git a/apps/files/src/actions/moveOrCopyAction.ts b/apps/files/src/actions/moveOrCopyAction.ts
index 42ae82bb261e3..a4e70caf37d11 100644
--- a/apps/files/src/actions/moveOrCopyAction.ts
+++ b/apps/files/src/actions/moveOrCopyAction.ts
@@ -89,8 +89,10 @@ export const handleCopyMoveNodeTo = async (node: Node, destination: Folder, meth
 	 *   Do not allow as it would copy foo within itself
 	 * - node: /foo/bar.txt, destination: /foo
 	 *   Allow copy a file to the same directory
+	 * - node: "/foo/bar", destination: "/foo/bar 1"
+	 *   Allow to move or copy but we need to check with trailing / otherwise it would report false positive
 	 */
-	if (destination.path.startsWith(node.path)) {
+	if (`${destination.path}/`.startsWith(`${node.path}/`)) {
 		throw new Error(t('files', 'You cannot move a file/folder onto itself or into a subfolder of itself'))
 	}
 
diff --git a/cypress/e2e/files/files_copy-move.cy.ts b/cypress/e2e/files/files_copy-move.cy.ts
index 235c5bc00c54b..7fd1b66e35042 100644
--- a/cypress/e2e/files/files_copy-move.cy.ts
+++ b/cypress/e2e/files/files_copy-move.cy.ts
@@ -87,6 +87,37 @@ describe('Files: Move or copy files', { testIsolation: true }, () => {
 		getRowForFile('new-folder').should('not.exist')
 	})
 
+	// This was a bug previously
+	it('Can move a file to folder with similar name', () => {
+		cy.uploadContent(currentUser, new Blob(), 'text/plain', '/original')
+			.mkdir(currentUser, '/original folder')
+		cy.login(currentUser)
+		cy.visit('/apps/files')
+
+		// intercept the copy so we can wait for it
+		cy.intercept('MOVE', /\/remote.php\/dav\/files\//).as('moveFile')
+
+		getRowForFile('original').should('be.visible')
+		triggerActionForFile('original', 'move-copy')
+
+		// select new folder
+		cy.get('.file-picker [data-filename="original folder"]').should('be.visible').click()
+		// click copy
+		cy.get('.file-picker').contains('button', 'Move to original folder').should('be.visible').click()
+
+		cy.wait('@moveFile')
+		// wait until visible again
+		getRowForFile('original folder').should('be.visible')
+
+		// original should be moved -> not exist anymore
+		getRowForFile('original').should('not.exist')
+		getRowForFile('original folder').should('be.visible').find('[data-cy-files-list-row-name-link]').click()
+
+		cy.url().should('contain', 'dir=/original%20folder')
+		getRowForFile('original').should('be.visible')
+		getRowForFile('original folder').should('not.exist')
+	})
+
 	it('Can move a file to its parent folder', () => {
 		cy.mkdir(currentUser, '/new-folder')
 		cy.uploadContent(currentUser, new Blob(), 'text/plain', '/new-folder/original.txt')