Strange mail problem

[Grant]

Until this morning everything was fine using Entourage.


Since this afternoon I keep getting error messages when trying to send mail to a specific address:

"Unable to establish a secure connection .. .. . ."

&
"The server does not support secure connections"


Using Entourage, I send a test message to another mail account of mine - the mail is sent & received perfectly.

So, I think to myself - must be a problem with the recipient email account / address I was trying to send to.


I boot into Win7.
The email account in Entourage is duplicated in Win7 using MS Outlook.
(both entourage & outlook are used for this one client only)

I try send the exact same email+attachment (pdf) from Outlook, to the same address I was unable to send to using Entourage.
The mail is sent without problem !

So evidently there is no problem with the recipient email account as it is sent perfectly from Outlook.
Entourage will send mail to other accounts without problem - but fails every time (since this morning) with this recipient.


What to do ??

 

[koffiejunkie]

What's the name of the SMTP server you're using? And port?

 

[])ragon_\/oid]

assuming that you are using outlook.com or office 365. Use exchange... That should help...

 

[koffiejunkie]

assuming that you are using outlook.com or office 365. Use exchange... That should help...

He said he's using Entourage. And weather it's Exchange or not makes no difference. Exchange uses certificates too.

 

[Grant]

What's the name of the SMTP server you're using? And port?

smtp.live.com
port 587

 

[Grant]

and now it is fine again

no setting were changed, no rebooting etc etc
just as suddenly it went bad, so it fixed itself !

 

[koffiejunkie]

smtp.live.com
port 587

and now it is fine again

I would suspect something running on your Mac (antivirus maybe) or on your network maybe. The certificate is valid from 24 April 2015 to 24 April 2016.