![outlook 2016 emails getting stuck in outbox outlook 2016 emails getting stuck in outbox](https://www.msoutlook.info/pictures/account-settings-pop3-advanced-server-timeouts.png)
I'm not super versed in Exchange, just recently took on the role of Systems Administrator, and am a little stumped. Why do emails get stuck in outbox Outlook When a message gets stuck in your Outbox, the most likely cause is a large attachment. She wants the purchasing account to be her primary send account, which it currently is, but as I stated above, emails get stuck in the outbox when using Outlook. If left at purchasing, it fails, but if moved to her account it works.)
![outlook 2016 emails getting stuck in outbox outlook 2016 emails getting stuck in outbox](https://www.slipstick.com/images/2011/02/delete-read-receipt-450x332.png)
Below that selection box is a using account option, where both her account and purchasing itself is at. (All the steps are: click the from box, select global address list, select purchasing. If we go through all of the steps to send an email from purchasing, using her account, it sends fine. If she sends from her own email, it works fine. If we log into it from OWA, it works fine. The issue is if she tries to send from purchasing, it get's stuck in the outbox. She also had send on behalf rights, but I recently removed them after reading about how having both can have issues. She has send as rights for the purchasing email account. Oh yes, on both machines I am only using multiple POP email accounts, including gmail. I've got a user who has two email accounts, her own, and a box that is technically a shared box for purchasing. Emails stuck in outbox (Outlook 2016) Some but not all emails get stuck in the Outbox with a draft icon instead of a ready to send icon.
![outlook 2016 emails getting stuck in outbox outlook 2016 emails getting stuck in outbox](https://www.technipages.com/wp-content/uploads/2012/09/Outbox-Search.png)
Hello, I've got an issue that I see others have had similarly before, by searching the subreddit here, and I'm looking for some assistance.