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some hotmail.com email address showing invalid certicate if sending from Mac mail app

I recently have a wired email issue with Mac Mail App.

I have an email address say, if I use this email in Mac Mail to send , the recipient side outlook will show invalid certificate.

But if I sent email using this address from web or outlook for Mac , no such issue.


I also have another email address say , doesn't have such issue.


contacted Microsoft email team, they blame Mac mail app since it works fine on the web or outlook for Mac.


what could go wrong?


I tried to remove and add back the email account , no fix


OS Monterey , Mac mail version 16.0




[Email Edited by Moderator]

Posted on Aug 24, 2022 8:35 PM

Reply
Question marked as Best reply

Posted on Aug 25, 2022 7:09 AM

fairwindw1 wrote:

I recently have a wired email issue with Mac Mail App.
I have an email address say, if I use this email in Mac Mail to send , the recipient side outlook will show invalid certificate.
But if I sent email using this address from web or outlook for Mac , no such issue.

I also have another email address say , doesn't have such issue.

contacted Microsoft email team, they blame Mac mail app since it works fine on the web or outlook for Mac.

what could go wrong?

I tried to remove and add back the email account , no fix

OS Monterey , Mac mail version 16.0



[Email Edited by Moderator]



If Mail on your Mac can't verify a server's certificate



Sign or encrypt emails in Mail on Mac - Apple Support



Use SSL to connect to the outgoing mail server in Mail on Mac





The current stable release of Monterey including bug fixes, is macOS 12.5.1


Keep your Mac up to date - Apple Support

Keep your Mac up to date - Apple Support



Similar questions

1 reply
Question marked as Best reply

Aug 25, 2022 7:09 AM in response to fairwindw1

fairwindw1 wrote:

I recently have a wired email issue with Mac Mail App.
I have an email address say, if I use this email in Mac Mail to send , the recipient side outlook will show invalid certificate.
But if I sent email using this address from web or outlook for Mac , no such issue.

I also have another email address say , doesn't have such issue.

contacted Microsoft email team, they blame Mac mail app since it works fine on the web or outlook for Mac.

what could go wrong?

I tried to remove and add back the email account , no fix

OS Monterey , Mac mail version 16.0



[Email Edited by Moderator]



If Mail on your Mac can't verify a server's certificate



Sign or encrypt emails in Mail on Mac - Apple Support



Use SSL to connect to the outgoing mail server in Mail on Mac





The current stable release of Monterey including bug fixes, is macOS 12.5.1


Keep your Mac up to date - Apple Support

Keep your Mac up to date - Apple Support



some hotmail.com email address showing invalid certicate if sending from Mac mail app

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