Hi @Aidil
Welcome to Microsoft Q&A forum
I understand you are facing an issue with attaching files in Outlook
To better understand, may I clarify a few details:
1.Are the files stored on your local hard drive, a cloud-sync folder (example: OneDrive) or anywhere else? Please ensure the file size is within the 20–25MB limit.
2.Is there an antivirus program installed on laptop? When temporarily disable antivirus/firewall, does the issue persist?
3.Have you tried on another device with the same account? Does the issue persist?
4.Have you tried with another account? Does the issue persist?
5.Have you tried on Outlook for web? Are you facing the same issue?
6.Please make sure your Outlook is the latest version
In the meantime, I suggest some further steps you can check:
1.Test Drag-and-Drop
-Open Outlook and start a new email.
-Navigate to the Files location.
-Drag the files and drop it into the email body.
-Check if the file attaches successfully
2.Change Email Format
-Open Outlook and start a new email.
-Go to Setting > Mail > Compose and Reply
-Under Message Format, check the “Compose messages in this format” dropdown, switch to Plain Text
3.Run Outlook in Safe Mode
-Close Outlook.
-Press Win + R, type outlook.exe /safe, and press Enter.
-Try attaching a file from the Desktop.
If it works, disable add-ins:
-In Outlook safe mode, go to File > Options > Add-ins, select COM Add-ins, click Go, uncheck all add-ins, and restart Outlook normally.
-Re-enable add-ins one by one to identify the problematic one.
3.Clear Outlook Cache
-Close Outlook.
-Press the Windows + R keys to open the Run box. Type %localappdata% into the box and press Enter.
-In the opened folder, select Microsoft >Outlook.
-In the next folder containing your Outlook profile and cache files. Find the RoamCache folder and double-click to open it.
-Select all files using Ctrl + A on your keyboard >right-click and select the Delete option.
4.Create a New Outlook Profile
-Close Outlook.
-Open Control Panel > Mail (Microsoft Outlook) > Show Profiles.
-Click Add, create a new profile, and set it as the default.
-Add your Exchange account to the new profile.
-Open Outlook and try attaching a file.
5.Repair Microsoft 365 Installation
-Go to Control Panel > Programs > Programs and Features.
-Select Microsoft 365, click Change, and run Quick Repair.
-If the issue persists, run Online Repair.
-Try attaching a file after repair.
6.Re-install Outlook
-Open Window menu > Settings > Apps > Installed apps
-Locate Outlook for windows > Uninstall
-Download new Outlook from the Microsoft Store
-Open Outlook, re-add your Exchange account
The initial response may not fully address your needs, but it will help me better understand your situation and try to find the root causes. I understand the urgency of your situation and appreciate your patience while we work through it
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