Email stuck in outbox

Question

Email stuck in outbox

Matt Cook 0

My email is stuck in the outbox and I don't know how to send it

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Kay Brennand-Millington (FCICM) 0 Reputation points

2026-09-01T10:20:37.8233333+00:00

I've just had my profile extended and now have 158 emails stuck in my Outbox as they were created using SAP Business One. Obviously going into each one and sending 158 times isn't a good option, can I bulk send them?
Kay Brennand-Millington (FCICM) 0 Reputation points

2026-09-01T10:23:18.87+00:00

By re-installing old Oulook and refreshing, I ws able to 'Send All'. What happens when Old Outlook is retired?
Hornblower409 16,335 Reputation points

2026-09-02T01:40:10.0666667+00:00

@Kay Brennand-Millington (FCICM) said

By re-installing old Oulook and refreshing, I ws able to 'Send All'. What happens when Old Outlook is retired?

Good question. I don't have any answers. Some of the more knowledgeable people on this forum might, but they will never see your comment on this old thread.

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2 answers

Kay Brennand-Millington (FCICM) 0 Reputation points

2026-09-01T10:20:37.8233333+00:00

I've just had my profile extended and now have 158 emails stuck in my Outbox as they were created using SAP Business One. Obviously going into each one and sending 158 times isn't a good option, can I bulk send them?
Kay Brennand-Millington (FCICM) 0 Reputation points

2026-09-01T10:23:18.87+00:00

By re-installing old Oulook and refreshing, I ws able to 'Send All'. What happens when Old Outlook is retired?
Hornblower409 16,335 Reputation points

2026-09-02T01:40:10.0666667+00:00

@Kay Brennand-Millington (FCICM) said

By re-installing old Oulook and refreshing, I ws able to 'Send All'. What happens when Old Outlook is retired?

Good question. I don't have any answers. Some of the more knowledgeable people on this forum might, but they will never see your comment on this old thread.

You need to start a new thread using the "Ask a question" button at the top of this page to create a new Question and include the details for that specific Question.

(You can put the link for this page in your new Question for reference)

Answer 1

Hi @Matt Cook,

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

Based on the details you shared, I understand your message is stuck in the Outbox in the new Outlook and will not send. I truly understand this impacts your workflow and appreciate the time you have already spent trying to fix it.

In many cases, this occurs because Outlook is not fully connected, an attachment is too large for the send limits, or the account cannot complete the outgoing authentication. Additionally, a sync queue can stall after a network change or a recent app update. The steps below are tailored to your situation so the message can leave the Outbox successfully.

Below are some alternative steps designed to address your situation effectively:

1/ Recreate and re‑send a clean copy

Open Outbox and double‑select the stuck message to open it.
If the email includes large attachments, remove them for now. As a best practice, upload big files to OneDrive and insert them as sharing links.
Copy the email content, create a new message, paste the content, re‑add the recipients, and then select Send.

2/ Confirm connection and run the in‑app troubleshooter

Look at the status indicator at the bottom of the Outlook window and confirm it shows Connected. If it shows Trying to connect, verify your internet connection and then try sending again.
Select the Help icon, choose Troubleshoot account, and let the diagnostic complete. Apply any suggested fixes related to send errors or sign‑in prompts.
Open Settings, choose View all Outlook settings, go to Mail, then Sync email. Confirm the account is Connected and, if prompted, sign in again to refresh your credentials.

3/ Clear the queue and refresh your session

In Outbox, move the stuck message to Drafts.
Select your profile picture, choose Sign out, and then sign back in to the new Outlook to start a fresh session.
Open the message in Drafts, re‑attach files as needed, and send the email. If it sends successfully, you can delete the older item that remains in Outbox.

If the message is still stuck after these steps, please reply with the approximate size of the email including attachments, whether this happens on different networks or only one, and any error text you see when you open the stuck message. I will take the next actions to get this sending promptly.

I hope this information is helpful. Please follow these steps and let me know if it works for you. If you have any updates regarding the issue, please feel free to share them with me.

Thank you for your patience and your understanding. I look forward to continuing the conversation.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Vy Nguyen 11,415 Reputation points Microsoft External Staff Moderator

2026-02-11T17:14:14.0666667+00:00

Hi @Matt Cook,

I hope everything is going well on your end.

I’m following up on the support thread we've been working through together. I wanted to check in and see if the information I shared in my previous answer helped resolve the issue you were experiencing.

If you're still experiencing any issues or have further questions, please feel free to reach out at any time. I’m always happy to help if you need anything else.

I want to ensure everything is functioning smoothly and that your experience remains seamless.

Thank you again for your collaboration throughout the troubleshooting process.

I look forward to hearing from you soon.

Answer 2

If your email is stuck in the Outbox in Outlook, there are a few potential causes and solutions you can try:

Send Immediately When Connected: Ensure that the Send immediately when connected option is enabled. You can check this by going to the File tab, selecting Options, then Advanced, and looking for the setting in the Send and receive section. If it is not enabled, enable it and click OK.
Deferred Delivery Rule: Check if you have a Deferred Delivery rule that might be delaying the sending of your email. To do this, go to Rules on the Ribbon, click Manage Rules & Alerts, and review the rules listed. Look for any rules that mention defer delivery by # minutes and adjust them as necessary.
Manual Send/Receive: You can manually initiate a send/receive operation by pressing F9 or selecting Send/Receive from the Ribbon. This can sometimes resolve the issue temporarily.
Check Add-ins: If you are using a Gmail account, certain add-ins may cause issues with sending emails. Compare your Outlook add-in list with a clean installation to identify any problematic add-ins.
Outlook Profile: If you are sending from a shared mailbox and your Outlook profile is configured in online mode, this may also cause emails to remain in the Outbox until manually sent.

By following these steps, you should be able to resolve the issue of emails being stuck in your Outbox.

References: