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Email wont send - Tried all previous thread responses

Dear Mac universe,


I'm using mac mail and emails are getting stuck in my outbox.

I am receiving emails, I just can't send them any longer.


The error message I keep receiving is:

I have searched the net and tried everything I could find to fix the issue

  1. checking stmp settings
  2. removing the account from icloud / reinstalling
  3. ensuring mail could be sent from icloud.com


At my wits end and need some guidance please.


Screenshot 1: Status shows online


Screen shot 2: Server Settings

Note: I have tried both (a) leavign username / password blank & (b) filling both in, with the same result


Screen shot 3: After completing (with / with out) username & password I get the same result ... "offline"



Hardware: 27" - Late 2012

OS: Catalina 10.15.7

Mac Mail: V 13.4


Truly appreciate any help you can offer.

MacBook Air 13″, macOS 11.2

Posted on Apr 18, 2021 12:33 PM

Reply
Question marked as Top-ranking reply

Posted on Apr 18, 2021 12:37 PM

Are you running any anti - virus programs? Using a VPN?


Try setting up another admin user account to see if the same problem continues. If Back-to-My Mac is selected in System Preferences, the Guest account will not work. The intent is to see if it is specific to one account or a system wide problem. This account can be deleted later. 


Isolating an issue by using another user account 


If the problem is still there, try booting into the Safe Mode using your normal account.  Disconnect all peripherals except those needed for the test. Shut down the computer and then power it back up after waiting 10 seconds. Immediately after hearing the startup chime, hold down the shift key and continue to hold it until the gray Apple icon and a progress bar appear. The boot up is significantly slower than normal. This will reset some caches, forces a directory check, and disables all startup and login items, among other things. When you reboot normally, the initial reboot may be slower than normal. If the system operates normally, there may be 3rd party applications which are causing a problem. Try deleting/disabling the third party applications after a restart by using the application un-installer or by using the developer’s uninstall instructions. For each disable/delete, you will need to restart if you don't do them all at once. 


Safe Mode - About.    


If it works in the Safe Mode, try running this program when booted normally and then copy and paste the output in a reply. The program was created by Etresoft, a frequent contributor.  Please use copy and paste as screen shots can be hard to read. Click “Share Report” button in the toolbar, select “Copy to Clipboard” and then paste into a reply. This will show what is running on your computer. No personal information is shown. If the log won’t post, try posting it in Pastebin and provide a link in a reply. After pasting the report in a PasteBin page, go to the top of the page, and copy the address in the URL bar. Paste that in a new reply.        Pastebin


https://etrecheck.com



Similar questions

3 replies
Question marked as Top-ranking reply

Apr 18, 2021 12:37 PM in response to Wooglin71

Are you running any anti - virus programs? Using a VPN?


Try setting up another admin user account to see if the same problem continues. If Back-to-My Mac is selected in System Preferences, the Guest account will not work. The intent is to see if it is specific to one account or a system wide problem. This account can be deleted later. 


Isolating an issue by using another user account 


If the problem is still there, try booting into the Safe Mode using your normal account.  Disconnect all peripherals except those needed for the test. Shut down the computer and then power it back up after waiting 10 seconds. Immediately after hearing the startup chime, hold down the shift key and continue to hold it until the gray Apple icon and a progress bar appear. The boot up is significantly slower than normal. This will reset some caches, forces a directory check, and disables all startup and login items, among other things. When you reboot normally, the initial reboot may be slower than normal. If the system operates normally, there may be 3rd party applications which are causing a problem. Try deleting/disabling the third party applications after a restart by using the application un-installer or by using the developer’s uninstall instructions. For each disable/delete, you will need to restart if you don't do them all at once. 


Safe Mode - About.    


If it works in the Safe Mode, try running this program when booted normally and then copy and paste the output in a reply. The program was created by Etresoft, a frequent contributor.  Please use copy and paste as screen shots can be hard to read. Click “Share Report” button in the toolbar, select “Copy to Clipboard” and then paste into a reply. This will show what is running on your computer. No personal information is shown. If the log won’t post, try posting it in Pastebin and provide a link in a reply. After pasting the report in a PasteBin page, go to the top of the page, and copy the address in the URL bar. Paste that in a new reply.        Pastebin


https://etrecheck.com



Apr 21, 2021 9:53 AM in response to Eric Root

Thank you for your comprehensive reply Eric.


I do have VPN's on my system, but they were not running when the issue was occurring.


Here's the outcome of your suggestions:

  • icloud mail: send / receive without any issues
  • Safe mode: Not able to send emails
  • Admin 2 account: created a new admin account, set-up mail and still no change
  • Account removal: Deleted and reinstalled - still no change
  • Etresoft: Been working through issues it's found across the system - still not change (attached)



Appreciate any additional help you can offer.

Apr 21, 2021 1:46 PM in response to Wooglin71

You are welcome. You might try uninstalling the VPN to see if that works. If it is still the same, reinstall it.


Troubleshooting Apple Mail


What does Mail/Window/Connection Doctor Show? If the server is red, select it and look at the Show Details box.


Mail: Mail troubleshooting 


Mail: If you can’t send messages.   


Troubleshooting sending email messages    


Mail not sending or receiving messages after updating OS X.      



Email wont send - Tried all previous thread responses

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