Do I need microsoft 365 to use outlook now?

Question

Do I need microsoft 365 to use outlook now?

Andrew Bertram 0

All of a sudden, my emails won't send. I use outlook on mac and have multiple old emails forwarding all to one. Now when i try to send an email it ends up in the Outbox, but never sends. When I tried to investigate is says my License is not active and it wants me to pay for microsoft 365. i have plenty of cloud storage available. If i have to i can just stop using microsoft emails all together. It will be a pain, but i can do it. Should i just do that or is there an error that will be corrected?

John Jefferson Doyon 86,980 Reputation points Independent Advisor

2026-08-20T03:56:50.39+00:00
Hi, @Andrew Bertram

No, you do not need a Microsoft 365 subscription to use Outlook for Mac with a personal email account. Outlook for Mac is free for personal Outlook.com, Gmail, iCloud, Yahoo, and IMAP accounts.

The "license is not active" message may be separate from why the emails are staying in the Outbox. Your available cloud storage would not determine whether Outlook itself is licensed.

To help narrow down the issue:

What type of email account is failing to send, Outlook.com/Hotmail, Gmail, Yahoo, or another provider?

If you sign in to that account through its webmail in a browser, can you send an email successfully?

Does this happen with every account added to Outlook, or only one particular account?

Also, what is the exact wording of the license message you see in Outlook?

Click "Add comment" to let me know.

Thanks!
Andrew Bertram 0 Reputation points

2026-08-20T11:57:00.0233333+00:00

an @msn.com account. and i havent tried to send anything from the independent site.
John Jefferson Doyon 86,980 Reputation points Independent Advisor

2026-08-20T21:58:17.58+00:00
Thanks for confirming.

Please sign in to Outlook on the web here: https://outlook.live.com/mail Then try sending a test email from there.

If it sends successfully on the website, the issue is likely with Outlook on your Mac rather than the MSN account itself.

If it also stays stuck or fails to send on the website, then the issue may be with the account or mailbox.

Also, when you see the "license is not active" message on the Mac, does Outlook still let you read and receive new emails normally?

Your answer

John Jefferson Doyon 86,980 Reputation points Independent Advisor

2026-08-20T03:56:50.39+00:00

Hi, @Andrew Bertram

No, you do not need a Microsoft 365 subscription to use Outlook for Mac with a personal email account. Outlook for Mac is free for personal Outlook.com, Gmail, iCloud, Yahoo, and IMAP accounts.

The "license is not active" message may be separate from why the emails are staying in the Outbox. Your available cloud storage would not determine whether Outlook itself is licensed.

To help narrow down the issue:

What type of email account is failing to send, Outlook.com/Hotmail, Gmail, Yahoo, or another provider?

If you sign in to that account through its webmail in a browser, can you send an email successfully?

Does this happen with every account added to Outlook, or only one particular account?

Also, what is the exact wording of the license message you see in Outlook?

Click "Add comment" to let me know.

Thanks!
Andrew Bertram 0 Reputation points

2026-08-20T11:57:00.0233333+00:00

an @msn.com account. and i havent tried to send anything from the independent site.
John Jefferson Doyon 86,980 Reputation points Independent Advisor

2026-08-20T21:58:17.58+00:00

Thanks for confirming.

Please sign in to Outlook on the web here: https://outlook.live.com/mail Then try sending a test email from there.

If it sends successfully on the website, the issue is likely with Outlook on your Mac rather than the MSN account itself.

If it also stays stuck or fails to send on the website, then the issue may be with the account or mailbox.

Also, when you see the "license is not active" message on the Mac, does Outlook still let you read and receive new emails normally?