Dear @Joe Matveyev,
I hope you’re having a good day.
Thanks for describing this in detail. Based on what you’ve shared, this does sound like a genuine and frustrating issue, and I appreciate how clearly you’ve outlined the behavior and how long it has been happening.
To help validate what you’re seeing, I’ve also tried testing this scenario on my own phone (iPhone 17 Promax) and checked with a few colleagues using similar devices and Outlook for iOS. In our cases, we weren’t able to consistently reproduce the unresponsive Send button or the draft‑loss behavior. That said, the fact that this issue occurs reliably on your device, across multiple iOS versions and Outlook updates still strongly suggests a client‑side problem rather than anything related to your Microsoft 365 tenant, license, or configuration.
What stands out is that the Send action becomes completely non‑responsive, not that the message fails after attempting to send. The fact that restarting the app immediately allows the same email to send points to Outlook for iOS getting into a stuck compose or app‑state condition. The occasional loss of drafts further reinforces that this is happening at the app level, not in Exchange or the Microsoft 365 backend.
Before escalating, there are a few basic troubleshooting steps worth trying if you haven’t already, as they can sometimes clear a corrupted app state on iOS:
First, Clear Outlook cache files on iPhone, Open the Outlook App > tap on your profile icon or picture located at the top left corner of the app > From the dropdown menu, choose “Settings” > Select the Account > In the account settings, choose the option to Remove the account. This action will remove the cached data associated with that account.
If the issue continues, the next step would be to remove the app completely. Uninstall Outlook from the iPhone, restart the device again, then reinstall Outlook from the App Store and add the account fresh. This effectively clears the local app cache.
If the behavior still persists after these steps, this is where deeper investigation is needed. At that point, if you’re an end user, the best next step would be to contact your Microsoft 365 administrator and ask them to raise a support ticket with Microsoft. Admins have access to the appropriate tools and support channels to collect diagnostic logs and work directly with the Outlook for iOS team to investigate this properly.
If you’re unsure who your administrator is, this article may help: How do I find my Microsoft 365 admin?
Your admin can raise support ticket from Microsoft 365 Admin Center>Support>Help & Support.
For reference: Get support | Microsoft Docs
I’m sorry to have to redirect you in this way, but my goal is to make sure you’re guided toward the path that can provide the most accurate and effective support. This is about ensuring the issue is reviewed with the right level of visibility and technical context.
If you receive any updates from your administrator or from Microsoft Support, or if you have additional questions in the meantime, please feel free to come back and share them here. I’m happy to help where I can.
Looking forward to hearing back from you with any updates or additional details.
Warm regards,
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