When you drag and drop a file onto a program on the taskbar while holding the Shift key and see the "Open with " message but nothing happens when you release the mouse, it could be due to various reasons. Here are a few troubleshooting steps you can try to resolve this issue: 1. Check Default Programs: - Verify that the program you are trying to use is set as the default program for that file type. - Go to Settings > Apps > Default Apps to adjust the default programs if needed. 2. Run as Administrator: - Try running the program you want to open the file with as an administrator. Right-click on the program icon and select "Run as administrator." 3. Restart the File Explorer: - Restarting the File Explorer process can sometimes resolve issues with drag and drop functionality. - Press Ctrl + Shift + Esc to open Task Manager, find Windows Explorer, right-click it, and choose Restart. 4. Check for Updates: - Make sure both Windows and the program you are using are up to date. Check for any pending updates in Windows Update and update the program if necessary. 5. Test with a Different File: - Try dragging and dropping a different file onto the program to see if the issue persists. It could be specific to that particular file. 6. Disable Third-Party Software: - Some third-party software, especially system optimization or security programs, can interfere with drag and drop functionality. Try temporarily disabling such software to see if it resolves the issue. 7. Create a New User Profile: - If the issue persists, creating a new user profile and testing the drag and drop functionality there can help determine if the problem is user-specific. If none of these steps solve the problem, it might be beneficial to perform a more in-depth troubleshooting process or seek help from the program's support team for further assistance.