r/Office365 • u/Boo-Woo76 • 1h ago
Classic Outlook emails with attachments stuck in Outbox; New Outlook fails to attach files, but web works
Hi everyone,
We’re troubleshooting Outlook issues affecting multiple employees. Our main problem is with Classic Outlook, and New Outlook is also having attachment issues.
Classic Outlook
- Text-only emails send successfully.
- Emails with attachments remain in the Outbox and are not sent.
New Outlook for Windows
- Attaching a file intermittently fails, even with small files.
- Error: “The following files couldn't be attached: [filename]. Please try again later.”
- Sending and receiving emails without attachments generally works.
What we’ve checked
- The same files attach successfully in Outlook on the web.
- Switching between corporate and external Wi-Fi makes no difference.
- Repairing/resetting New Outlook and clearing its app data did not resolve it.
- A factory-reset PC without corporate security software works, although other differences between PCs have not yet been ruled out.
- Some users work normally while others fail, even with exactly the same versions:
- Outlook: 1.2026.1001.200
- Client: 20261002003.17
- WebView2: 155.0.4283.45
Our DLP vendor reports no known update-related issue, but we haven’t confirmed or ruled out a security software interaction.
For context, we use two company email domains: one provided by HQ and one purchased by the regional office. This does not necessarily mean they share the same mail infrastructure; we’re still separating the findings by account/domain.
Colleagues in other offices have reported similar problems around October 14. We’re contacting Microsoft support and using web Outlook as a temporary workaround.
Has anyone recently experienced this combination of symptoms? If you found the cause, which diagnostic logs or specific component helped identify it?
Thanks!
