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Unable to send encrypted emails in Outlook for Mac and Outlook.live.com (admin account) since 03/13

CND 0 Reputation points
2026-03-18T17:43:49.97+00:00

Details: I am unable to send encrypted emails using both Outlook for Mac and Outlook on the web (outlook.live.com). This issue started on Friday, 03/13, and has persisted since then.

When attempting to send encrypted emails, the feature does not work as expected. I previously contacted support, but the issue was not resolved. I was advised to contact the admin; however, I am the admin for this account.

Additional details:

Microsoft 365 subscription (personal, not business)

Using Outlook for Mac and Outlook on the web (outlook.live.com)

Encryption was working previously and stopped suddenly on 03/13

Issue occurs across multiple browsers, including Google Chrome

I have tried signing out/in and basic troubleshooting with no success

I am still unable to send encrypted emails from any platform

This is impacting my ability to send secure communications. Please advise on how to restore encrypted email functionality or escalate this issue for further investigation.

Outlook | Web | Outlook.com | Email
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Answer recommended by moderator
  1. CND 0 Reputation points
    2026-03-18T19:54:58.63+00:00

    The message just wouldn’t send when encryption was turned on. This also happened when replying to already encrypted emails.

    My setup:

    • Microsoft 365 personal subscription (active)

    Regular Outlook.com email (no custom domain)

    Encryption was working fine before

    Issue started suddenly (no changes on my end)

    Happening on both Mac app and web

    What didn’t help:

    Signing out/in, switching browsers, etc.

    Setting up a digital ID (S/MIME) → not relevant in this case

    Being told I needed a work account or custom domain

    What fixed it:

    Honestly, it got fixed after Microsoft support looked into my account. I didn’t change anything on my end.

    What this likely means:

    This seems to be a backend/account issue, probably related to:

    Encryption (OME) on the account

    Licensing or something on Microsoft’s side

    Temporary service issue

    Takeaway:

    If encryption suddenly stops working everywhere (desktop + web), it’s probably not your setup.

    Best thing to do:

    Contact Microsoft support

    Ask them to check your encryption/OME status or account configuration

    Push for escalation if they keep suggesting basic troubleshooting

    In my case, it just started working again after they checked my account.I ran into an issue where I couldn’t send encrypted emails in both Outlook for Mac and Outlook on the web (outlook.live.com). The message just wouldn’t send when encryption was turned on. This also happened when replying to already encrypted emails.

    My setup:

    Microsoft 365 personal subscription (active)

    Regular Outlook.com email (no custom domain)

    Encryption was working fine before

    Issue started suddenly (no changes on my end)

    Happening on both Mac app and web

    What didn’t help:

    Signing out/in, switching browsers, etc.

    Setting up a digital ID (S/MIME) → not relevant in this case

    Being told I needed a work account or custom domain

    What fixed it:

    Honestly, it got fixed after Microsoft support looked into my account. I didn’t change anything on my end.

    What this likely means:

    This seems to be a backend/account issue, probably related to:

    Encryption (OME) on the account

    Licensing or something on Microsoft’s side

    Temporary service issue

    Takeaway:

    If encryption suddenly stops working everywhere (desktop + web), it’s probably not your setup.

    Best thing to do:

    Contact Microsoft support

    Ask them to check your encryption/OME status or account configuration

    Push for escalation if they keep suggesting basic troubleshooting

    In my case, it just started working again after they checked my account.

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