Outlook no longer receives or sends mail

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I have used Microsoft Outlook for mail on my iMac for several years. 2 days ago it just stopped sending and receiving mail. I have 2 factor identification on my Gmail account and tried generating a new password which i loaded into Outlook in the Password field in Tools/Accounts. What has happened and how can I fix this?
 

Raz0rEdge

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What errors are you getting when you try to send or receive email? Have you tried other apps with the same settings?
 
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Have you checked to see if there is an update for Outlook? What specific version are you using?
 
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I have used Microsoft Outlook for mail on my iMac for several years. 2 days ago it just stopped sending and receiving mail.


Can you access your Gmail account using webmail and does everything work correctly there???

Can you think of anything you might have changed within the last couple of days???

Do you have a bootable clone you could try using that was created three or four days ago or when everything was working???



- Patrick
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When I hit SEND & RECEIVE I get the error message “A message could not be sent” with details “The message could not be sent because it has unresolved recipients” The following messages messages displayed at the bottom RHS of Outlook window “Sync pending for this folder” and “Connected to [email protected]” but no mail coming in or being sent.

I have tried deleting my email account under TOOLS/ACCOUNTS and reinstalling it. The account duly loaded up my entire email history and worked for a day before developing the same problem i.e. it stopped sending and receiving email so I am back to where I started.
 
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Hi Patrick. I have access to my Gmail account which is working fine. I cannot think of anything that has changed in the last couple of days. I am afraid that I do not know what a bootable clone is but I do have a Time Capsule that backs up my iMac.

- - - Updated - - -

I am currently using Microsoft Outlook for Mac Version 16.16.9 (190412)
 
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@Dale
I am afraid that I do not know what a bootable clone is but I do have a Time Capsule that backs up my iMac.


A "bootable clone" is a complete clone (backup) of your data and a working OS X System that's backed up normally onto an external drive that can be used to boot your current Mac or another similar compatible model.

Third-party applications such as Carbon Copy Cloner (CCC) or SuperDuper! (SD!) are usually used to create a bootable clone. A Time Machine backup is supposed to work as a bootable clone, but I have never had very much success trying to do so, and maybe only from 2016 or later OS X versions. And I don't really know if it would work from a Time Capsule, but Apple says it will with a:
External drive connected to an AirPort Extreme Base Station (802.11ac model) or AirPort Time Capsule
Back up your Mac with Time Machine - Apple Support

For more info, google what is a "bootable clone" Mac
what is a "bootable clone" Mac - Google Search


- Patrick
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