- If Outlook freezes when attaching files, try rebooting the app as a first step.
- Check that the problem is happening with all attachments and not just one specific file.
- Try opening the app in safe mode, disabling add-ins, or deleting and reinstalling the app.
The ability to add attachments to emails means that you can perform tasks as diverse as sending a funny meme or updating your boss with the latest figures in an Excel sheet. So, if Outlook freezes when attaching files, it can be very frustrating.
Before you work through the steps below, try rebooting the app. Just close it and re-open it, and try attaching the file again. Also, it’s worth trying the attachment process with more than one file. It could be a problem with a specific document.
If you’re still stuck, read on to find three methods that should help if Outlook freezes when attaching files.
If Outlook Freezes When Attaching Files, Try Opening in Safe Mode
Step 1. Close your Outlook app with the “X” icon in the top right corner.

Step 2. Press the Windows key + “R” simultaneously to open the “Run” box.

Step 3. Type this in exactly: “outlook.exe /safe”.

Step 4. Press “OK,” and Outlook should open in safe mode, which means it’s in a default state with no add-ins activated. Try to attach the file again. If it works, you know there’s a problem with an add-in, and you can move on to the next step.

If you still find that Outlook freezes when attaching files, head straight to the final step of uninstalling and reinstalling the app.
Manually Disable Add-Ins

Step 2. Ignore the big button that says “Manage Add-ins” as this will open up web-based Outlook and only allow you to make changes to email in your web browser. Instead, look for “Options,” located toward the bottom left.

Step 4. From here, you can use the scientific method to manually disable add-ins one by one. Try attaching the file to the email after every change, so you can understand which add-in is causing the problem. For example, if you switch Adobe Document Cloud off, and the attachment works fine, you know that this add-in is corrupt or incompatible.

Delete and Re-Install Outlook
Step 1. If none of these steps work, try uninstalling and reinstalling Outlook. To uninstall the app, head to “Settings” then “Apps.” You can reach settings by searching for it or pressing the Windows key and “I” at the same time.

Step 2. Click on “Installed apps,” and scroll to Outlook. Alternatively, you can use the search function at the top of the screen.

Step 3. Click the three dots and then click “Uninstall.” Follow all the onscreen prompts until the uninstallation is complete.

Step 4. Head to the Microsoft Store, again, by using the search function on your home screen.

Step 5. Search for “Outlook” in the Microsoft Store. Click “Get” or “Install” and follow the onscreen instructions. Once installed, the “Install” icon will change to “Open.”

You should now be able to attach files to Outlook emails without it freezing or crashing.