Apple Mail - "An SSL error has occurred and a secure connection to the server cannot be made."

I get this message frequently, but I am always able to send after about 2 or 3 reclicks. This started sometime last year after probably a OS update.


Is there any fix for this, or should i just live with it?


I only wish Apple mail were easier to troubleshoot. I still have a couple emails I cannot send out with, no matter how many times I've deleted and reentered them. Only so much time in the day to deal with these things. ;-)



Has this process been improved for Catalina?

Posted on Jan 16, 2020 9:13 AM

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Posted on Jan 16, 2020 11:09 AM

Check your email app's configuration. You should have the correct addresses for the incoming and outgoing mail servers. Select SSL security in their configurations. You need two port settings: incoming is usually 143 for SSL; and outgoing is usually 587 for SSL. However, these may change depending upon your email provider. Check with your provider to obtain the required information.

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Jan 16, 2020 11:09 AM in response to Mr.Snak

Check your email app's configuration. You should have the correct addresses for the incoming and outgoing mail servers. Select SSL security in their configurations. You need two port settings: incoming is usually 143 for SSL; and outgoing is usually 587 for SSL. However, these may change depending upon your email provider. Check with your provider to obtain the required information.

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Jan 16, 2020 1:48 PM in response to Kappy

I've always done this. Server settings are currently exactly what the email provider wants.


As mentioned, the issue is not consistent. The email goes through, but only after a couple-three retries after getting that error message.


The other problem is making clear sense of the three areas Apple has for email adjustments.

• A truncated account setup in Apple Preferences under Internet Accounts

• The fuller version in Apple Mail Preferences, but few options.

• Mail Connection Doctor seems to have the most options, but hard to match email accounts with in and outgoing servers. Port settings are not easy to find. I always forget where they are.

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Apple Mail - "An SSL error has occurred and a secure connection to the server cannot be made."

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