Thanks — that’s a clear description and a very common (and maddening) symptom. Quick summary of what’s likely happening and an ordered set of tests/fixes you can run — start at the top and stop when the problem is gone. I’ve highlighted a few things Microsoft/forum posts tie to Snipping/Clipboard/Capture bugs and Outlook connectivity/add‑ins so you know these are known vectors to check. p a new Outlook message the image is stored as an inline/temporary resource. If Outlook can’t finish the send (connectivity, service hiccup, add‑in/AV interference, or an Outlook bug), the client saves the message to Drafts — often stripping the temp inline image, leaving an empty draft. This can happen even though you think “Send” was clicked.
Quick tests (5 minutes)
- Send the same message from Outlook office.com) right after creating it.
- If it appears in Sent in the web client, the desktop client is the problem. If it doesn’t send from web either, it’s a server/tenant issue.
- Save the snip to disk (Snipping Tool: Save or Ctrl+S) then Attach > This Device > choose file and Send.
- If that sends reliably, it suggests a clipboard/inline image handling issue.
- Create a plain test message (no image) and send — does it go to Sent?
- Confirms whether the issue is specifically with images.
If web Outlook shows sent OK: focus on desktop Outlook.
Suggested fixes (ordered, go one at a time)
A. Quick connectivity + status checks
- Check Outlook’s status bar: does it say Connected / Online / Working Offline? If it’s Offline or has “Trying to connect”, the message may be saved to Drafts. Also check the Sent folder in web Outlook (confirms server delivery). Service outages / slowness can cause these problems.
B. Test in Safe Mode (check add‑ins)
- Close Outlook, run: outlook.exe /safe
- Compessage with a pasted snip.
- If it sends in Safe Mode, disable COM add‑ins: File → Options → Add‑Ins → Manage COM Add‑Ins → Go → uncheck all → restart Outlook. Then re-enable one-by-one to find the culprit. (This is a common diagnostic step.)
C. Clipboard / Snipping Tool workaround
- Instead of paste, save the snip to a file and attach it. Or us From File. If that works reliably, use it as a workaround and continue troubleshooting the clipboard/inline flow. The Snipping Tool / Capture Service has had bugs around clipboard/inline handling in some Windows builds — keep this in mind while testing.
D. Antivirus / Email‑scanning interference
- Temporarily disable any “email scanning” feature in your AV/Security suite and tblock/strip inline resources while scanning outgoing mail causing Outlook to abort the send and save as Draft.
E. Outlook profile / OST issues
- Turn off Cached Exchange Mode (temporarily) and try sending (Account Settings → Change → uncheck Cached Exchange Mode) — or recreate the Outlook profile (Control Panel → Mail → Show Profiles → Add) and test from the fresh profile. Corrupt cache/OST can behave strangely and drop inline resources.
F. Clear temporary Outlook image temp cache
- Outlook stores inline images in a temp folder. Clearing Internet Explorer / Edge cached files and thee sometimes helps:
- Close Outlook.
- Delete files under: %localappdata%\Microsoft\Windows\INetCache\Content.Outlook\ (don’t delete the folder itself).
- Restart Outlook and test.
G. Enable Outlook logging (if you want detailed troubleshooting)
- File → Options → Advanced → enable “Enable troubleshooting logging (requires restart)”.
- Reproduce the issue, then attach the log files here (if you want me to read them) and I’ll help interpret. Enabling logging helps catch send errors and why Outlook chose Drafts.
H. Repair Office / Update / Reset Snipping Tool
- Even though you said everything’s up to date, run:
- Control Panel → Programs → Microsoft Office → Change → Quick Repair (try Online Repair if Quick Repair doesn’t fix).
- Update Office: File → Office Account → Update Options → Update Now.
- Consider resetting or re-installing Snipping Tool via the Microsoft Store if you suspect its clipboard integration is buggy. Microsoft has acknowledged Capture Service / Snipping Tool issues in some builds.
Extra diagnostics to run and report back
- Does this happen only with the Snipping Tool or with any image copied from any app (Paint, Photos, PrintScreen)?
- Are you Windows” (the one that is a UWP/WinUI app) or classic Outlook 365 (32/64-bit)? That matters for troubleshooting steps.
- What account type? (Office 365 / Exchange Online, or IMAP/POP?) Exchange Online accounts behave differently than POP/IMAP when the client is offline.
- Try sending while on a different network (phone hotspot) to rule out local network/proxy issues.
Why I cited those items
- There are known Snipping Tool / Capture Service bugs and reported Outlook service slowdowns that create exactly this behavior (send appears to fail and messages land in Draft or Outbox with images lost). The files I pulled from forum archives describe these problem vectors and the standard troubleshooting approaches.
If you want, I can walk you through:
- Running Safe Mode and disabling add‑ins step‑by‑step.
- Enabling logging and collecting the log files and interpreting the send failure.
- Recreatingnsck tests (OWA send, attach a saved snip, and Safe Mode). Post results and the exact Outlook app name/version and account type, and I’ll give the next best action.
