Using New Outlook on Windows for personal email, calendar, and contact management
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Please reply with only these details:
- Do the same attachments send correctly from Outlook.com on the web?
- What are the file sizes of the affected JPEG and DOCX files?
- Are recipients using Outlook, Gmail, Apple Mail, or another mail app to open them?
- Does sending as a OneDrive link work correctly?
Please try the steps below:
1) Test the same files from Outlook.com on the web
Sign in to https://outlook.live.com/mail/ in a browser, create a new test email, attach the same JPEG and DOCX files, then send them to yourself and one external address.
- If the attachments arrive correctly from Outlook.com on the web but not from New Outlook for Windows, the issue is likely related to the New Outlook app or the local upload process.
- If the attachments are also corrupted from Outlook.com on the web, the issue may be related to the files, account, network, or recipient-side handling.
2) Send the files as OneDrive links instead of normal attachments
Upload the affected files to OneDrive, then share them as links instead of attaching local copies.
Use a cloud sharing service, such as OneDrive, as a workaround for attachment size or upload issues. OneDrive links also do not count toward the Outlook.com email size limit. You can refer to these articles:
3) Compress the files before sending
Put the JPEG or DOCX files into a ZIP file, then send the ZIP file instead.
4) Check the attachment size before sending
For Outlook.com, the file attachment size limit is 25 MB. If the files are close to or above the limit, use OneDrive links instead. See: Sending limits in Outlook.com.
5) Test another sending method as a temporary workaround
If Outlook.com on the web sends the same attachments correctly, please use Outlook.com on the web or another mail app temporarily for important attachments while troubleshooting New Outlook.
6) Repair or reset New Outlook
In Windows, go to: Settings > Apps > Installed apps > Outlook (new) > Advanced options
Then try the following:
- Select Repair first.
- If that does not help, select Reset.
- Add the account again if needed.
- Test again with a small JPEG and DOCX file.
Please tell me how it goes. If the problem persists, please don’t hesitate to reply to this thread and I will be happy to help. Have a lovely day!
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