Fix Microsoft 365 encrypted email one-time passcode delivery failure

draft · accounts-and-access password-resetmicrosoft-365

Generated by docuprocessor (prompt article/v3) · 2026-04-22 08:20

Source thread

thread_id: spaces/AAAA05BdS6s/threads/hS0FPuFnwkg · 3 msgs · first 2024-06-27 · participants: Tech ATech B

Tech A 2024-06-27 14:44

Hey guys, I'm working at Costal Endo office. They are receiving encrypted emails from O365. They receive an email with a button to sign in to their work or school account at O365, or they can get a One Time Passcode. If I try to get a One Time Passcode, I never get it. The email address is correct. Does anyone had this issue before? If I try to log in with their email account, it says that that account doesn't exist. But if I log in to outlook365 portal with that email, works. I think that's because it's a personal account, not a work one.

image/png image.png

The screen displays a **Microsoft Office 365 Message Encryption** one-time passcode (OTP) entry page, stating the passcode will expire in **15 minutes**. A redacted email address is shown as the delivery destination. Options visible include a passcode entry field, a "keep me signed in for 12 hours" checkbox, a **Continue** button, and a link to request another passcode.

Tech B 2024-06-27 15:55

Check if domain requires renew, check for email connections (the one's responsible for sending emails and ports) If there is smtp between server and recipent... - Expired SSL cert could cause similar issue This looks like issue related to sending email

Tech B 2024-06-27 15:56

easyest way to identify issue: https://learn.microsoft.com/en-us/microsoft-365/enterprise/view-service-health?view=o365-worldwide

---
title: "Fix Microsoft 365 encrypted email one-time passcode delivery failure"
category: accounts-and-access
tags: ["password-reset", "microsoft-365"]
source_thread_id: "spaces/AAAA05BdS6s/threads/hS0FPuFnwkg"
source_space: "spaces/AAAA05BdS6s"
generated_at: "2026-04-22T08:20:31"
participants: ["Tech A", "Tech B"]
---

# Fix Microsoft 365 encrypted email one-time passcode delivery failure

## Problem
Office receiving Microsoft 365 encrypted emails cannot access the content. When attempting to use the one-time passcode option, the passcode never arrives at the recipient's email address. The "sign in to work or school account" option fails with an error stating the account doesn't exist, even though the same email address works when logging into the Outlook 365 portal directly. This suggests the recipient has a personal Microsoft account rather than a work/organizational account.

## Resolution
1. Check the Microsoft 365 service health status at https://learn.microsoft.com/en-us/microsoft-365/enterprise/view-service-health?view=o365-worldwide to identify any ongoing service issues
2. Verify the domain's SSL certificate has not expired, as expired certificates can prevent encrypted email delivery
3. Check SMTP connectivity between the sending server and recipient to ensure email routing is functioning properly
4. Confirm email connection settings and ports are configured correctly for the recipient's email system
5. If the recipient has a personal Microsoft account rather than an organizational account, they may need to use alternative methods to access the encrypted content or contact the sender to use a different encryption method

## References
- Source discussion: `spaces/AAAA05BdS6s/threads/hS0FPuFnwkg`
- Attachments: - ![image.png](../attachments/hS0FPuFnwkg.hS0FPuFnwkg/image.png) — The screen displays a **Microsoft Office 365 Message Encryption** one-time passcode (OTP) entry page, stating the passcode will expire in **15 minutes**. A redacted email address is shown as the delivery destination. Options visible include a passcode entry field, a "keep me signed in for 12 hours" checkbox, a **Continue** button, and a link to request another passcode.

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