Mail on Mac and iPhone: all my outgoing servers stopped working

NK1988 wrote:

Something very weird happened: all my outgoing servers stopped working in Mail for Mac and iPhone, for all my email addresses (some are Gmail, some are external provider with own hosting).

I've tried disconnecting and deleting the addresses and setting up everything again, but the problem remains. Yet all parameters are correctly inputted. When I check my connection doctor, it confirms Mail can't connect to any of the SMTP.

Anyone else running into these issues? Any idea what else I can look at?

Server issues are best resolved by your ermail provider—this would be out of your control.

If it is a local issue than look at the Connection Doctor>Show Details

Use Connection Doctor in Mail on Mac - Apple Support

If you can't send emails in Mail on Mac - Apple Support

NK1988 wrote:

hey Douglas, thanks for the quick reply.

I've already contacted my hosting provider but i can still send and receive emails if I use webmail, so we ruled out a problem on their end. Moreover, this is affecting all my emails, including my gmail addresses, which is why my conclusion is that the problem lies with Mail.

The Connection Doctor just says to check my network connection (works fine) and that the correct information is entered in the account preferences (checked and double-checked). When I ask to see the details/logs, they are empty pages.

I'm really lost here!

Old issue, new issue, what changed...?

The current stable release of Monterey including bug fixes, is macOS 12.6

Keep your Mac up to date - Apple Support

Keep your Mac up to date - Apple Support

Update your iDevice  - The current stable release of iOS including bug fixes, is iOS 16.0.2

Update your iPhone or iPad - Apple Support

Try turning off the bells and whistle, Mail issues in macOS Monterey.

—Open mail app select Mail>Preferences>Privacy  disable:

• “Protect Mail Activity” / 
• “Hide IP address” / 
• “Block all remote content”

Use Mail Privacy Protection on Mac - Apple Support

 Use Mail Privacy Protection on Mac - Apple Support

— Hide My email—Disable this feature if no resolve and compare your results...

Set up and use Hide My Email in iCloud+ on all your devices - Apple Support

— iCloud Private Relay on Mac - Apple Support

Use iCloud Private Relay on Mac - Apple Support

issues with Private Relay Unavailable it could also be your network settings ...

... 'limit IP tracking in mail and safari' will kill private relay if turned off. Turn it on, then reboot if used.

ref: https://support.apple.com/guide/icloud/set-up-icloud-private-relay-mm7dc25cb68f/icloud

Uninstall  all third party apps that are Cleaners/Optimizers/Anti-Virus/VPN

all known to cause issues on the macOS

NK1988 wrote:

That really got my hopes up, but unfortunately i'm still running into the same issue.

I've updated to Monterey 12.6, tried all options you gave, disabled cleanmymac, nothing seems to change a thing.

I'm totally lost, I'm sorry.

Remove your "cleanmymac"... it is one of the worst—look for the official uninstaller.

if in doubt search the developers website or contact their: Support/Help/FAQ/Known issues/compatibility/Updates/uninstaller

Contact a third-party vendor - Apple Support

After that you may have to reinstall the macOS to repair the macOS.

How to reinstall macOS— Recovery (both M1 and Intel) — How to reinstall macOS - Apple Support

Rule number #1 on Mac— do not install garbage apps...