Mail App won't send

[sleeperjeff]

MAC mini 2018, OS 10.15.5, 3.2 GHz i7, 32 GB RAM MAC Mail app, iCloud mail account


One day I could not send mail anymore. That's it. I made no changes to the settings, it just stopped sending email. Dumps it in the outbox. I CAN send from the iCloud website. I CAN send from my iPhone using the same internet connection my MAC is on. (WiFi) Have reset the PRAM, SMC, checked all the mail settings: Outgoing mail Account shows as "iCloud", account is enabled, says is online (green dot).

Error message is: "The connection to the server "smtp.mail.me.com" on port 587 timed out."
I also get "An SSL error has occurred and a secure connection to the server cannot be made."

The box for Use TLS/SSL is checked.
Authentication is "None"

I think it keeps taking the SMTP offline but IDK why. I tried using the Spark app but it does the same thing.

Any help would be appreciated.

Jeff

 

[hg.wells]

Hi Sleeperjeff,

resetting the SMC and PRAM won’t help with things like mail issues.

I would suggest either remove the iCloud account from mail and re-adding it. Or having a look at the settings in the Apple support page. You have things like authentication turned off, which should be on.

iCloud Mail server settings for other email client apps - Apple Support

Use these iCloud Mail server settings to manually set up your iCloud Mail account in an email client app.

support.apple.com

 

[sleeperjeff]

Thanks for the suggestions. I already did the delete account maneuver to no avail.
Authentication has several choices see the attached screen shot.
I never had to configure that before it was all automatic.
Again, Thanks for your assistance.

Jeff

 

[hg.wells]

Have you closed mail and tried removing and adding the account again through iCloud under system preferences?

 

[BrianBaughn]

Spark does the same thing? Sounds like it's not a Mail issue.

Do you have any anti-virus or firewall-type software on the Mac?

What are your DNS settings at System Preferences>Network>Advanced>DNS?

 

[sleeperjeff]

Sorry I've been gone from home.. I already tried the delete account maneuver.
I have anti virus software but I've had it the entire time when the mail was working just fine. I've gone more than a year when this happened before, unfortunately I can't remember the remedy from the last time.

Another thing I just realized is that I am subscribed to apple music and it works only on my iPhone but not on my computer anymore. It seems like I am not getting logged in correctly to Apple by my computer.

 

[hg.wells]

Sounds like your iCloud account isn’t syncing properly, it maybe worth signing out and back in again in system preferences then.

 

[sleeperjeff]

Done it no avail. Now when i select iCloud for my outgoing mail server it changes itself to "none" after a few seconds

 

[sleeperjeff]

been getting this off and on

 

[hg.wells]

How are you removing the mail account? And iCloud account?

it sounds like it’s keeping settings which it shouldn’t be doing if they are removed.

Mails preferences shouldn’t show any accounts listed, if it does it’s just going to reuse the existing problematic settings when enabled again.

 

[BrianBaughn]

You didn't respond to my question about your DNS settings.