File Sharing from a Microsoft Application and Sending Copy's as PDF or native Microsoft Application format is Delayed

Question

For example from Word, If you go to File >> Share >> More Options (...) >> Send Copy >> Word Document or PDF and then send a document or Microsoft native document from the originating Microsoft Application, the email will be extremely delayed and is does not reside in your Outlook Sent or Outbox.

There is another client that's being used to send the document, I suspect, and this is not at the receivers end b/c the receiver eventually gets it but it may take 2-3 days to 1-2 weeks.

What client is the Share feature using?

Answer 1

The answer is: There is another Microsoft Outlook (Classic) client on everyone's machine and until you open it up, things are stuck in that outbox. Why they eventually free up and send, I would like to know.

Microsoft - you can do better!

Answer 2

This automated answer is great for troubleshooting but I CHALLENGE the reader, help desk person, etc, to actually execute this on their own and I guarantee it will happen.

What other Microsoft email client is on my laptop?

Answer 3

Dear @Brian Katz,

Thank you for posting your question in the Microsoft Q&A forum.

Based on your description, File sharing from a Microsoft application, when sending a copy as a PDF or native format, is delayed and does not appear in Outlook Sent Items or Outbox and you concern about what client the Share feature using is. For better understanding your situation, could you please provide us more detail information as:

Have you tried to test to send the same file in two ways? (if you have not tried it, please help us to try to check where the issue come from), you can try to send it to your colleague or to yourself to check.

• Send a normal email by attaching the file.
• Send it using Word’s “Share” feature to see if the behavior is the same

If both methods are delayed, then the issue is with the mail system, not how Word works with Outlook. Also, mail stuck in the Outbox can be caused by several factors, such as checking the internet connection.

If testing shows the issue is with Word and Outlook, you should try some troubleshooting steps to resolve it.

If Outlook has On‑Send add‑ins or is on certain builds, those add‑ins can block or dramatically delay the send operation—even though the recipient eventually gets the email.

Outlook email is delayed while a web add-in is working on the send request

Here are some more suggestions to resolve delays when sending from Office via Outlook:

• Update Outlook to a build that contains the On‑Send fix (e.g., Current Channel ≥ 17628.20144). Open Outlook and select File > Office Account > Update Options > Update Now.
• Temporarily disable On‑Send add‑ins: In Outlook, select File > Manage Add‑ins (or Options > Add‑ins) and turn off any add‑ins that run “On send.” Retry the Share > Send a copy action.
• Use Outlook on the web (OWA) to test: Save as PDF/Docx, attach in OWA, and send. If OWA works, the issue is local to the Outlook client/add‑ins.
• Check attachment size & mailbox storage: If the message sits in Drafts, remove large attachments or clear mailbox space, then send again.

Looking forward to your update, please understand as a forum moderator, we're trying our best to find the effective solutions for you

If you have any other questions, please feel free to reach out.

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