Q: can no longer send mail after installing Yosemite

When I installed Yosemite on my macbook air, I can send mail thru Gmail, but not thru my provider SMTP, and setting where unchanged since previous system version where it was sending correctly.

SSL : password security, but SSL certificate expired. This could explain the refusal to send mails in Mail App in Yosemite.

I'm having this same problem. Connection Doctor gives all green dots. Nothing seems to be changed in my settings since upgrading, but mail just sits in my outbox. Need this fixed pronto!

Did they give you any tips on fixing it on your mac?

I am having the exact same problem.

Hi nwpmike,

When I uncheck "SSL" it's working well, but it's not very secure. When I leave SSL, I got in "Connection Doctor" the message "Trying to log in to this SMTP account failed. Verify that the username and password are correct.", only for the SMTP. For the IMAP, the status in Green. It's also working well on the iPhone 6 with ios8 and other mac with OS X 10.9 and previous versions.

The only thing that can be involved is that the certificat used by my mail provider is expired.

With connection docteur, there is a button "Show Details". Here is the conversation when connecting to the smtp.

READ Oct 18 23:33:53.363 [kCFStreamSocketSecurityLevelNone] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6000014a58e0 -- thread:0x600001e6fbc0

250-smtp.planet-service.fr

250-AUTH LOGIN CRAM-MD5 PLAIN

250-AUTH=LOGIN CRAM-MD5 PLAIN

250-STARTTLS

250-PIPELINING

250 8BITMIME

WROTE Oct 18 23:33:53.363 [kCFStreamSocketSecurityLevelNone] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6080010b1400 -- thread:0x600003479b00

STARTTLS

WROTE Oct 18 23:33:53.363 [kCFStreamSocketSecurityLevelNone] -- host:smtp.planet-service.fr -- port:587 -- socket:0x600000ab43a0 -- thread:0x6080032654c0

STARTTLS

WROTE Oct 18 23:33:53.364 [kCFStreamSocketSecurityLevelNone] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6000014a58e0 -- thread:0x600001e6fbc0

STARTTLS

READ Oct 18 23:33:53.432 [kCFStreamSocketSecurityLevelNone] -- host:smtp.planet-service.fr -- port:587 -- socket:0x600000ab43a0 -- thread:0x6080032654c0

220 ready for tls

READ Oct 18 23:33:53.432 [kCFStreamSocketSecurityLevelNone] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6080010b1400 -- thread:0x600003479b00

220 ready for tls

READ Oct 18 23:33:53.433 [kCFStreamSocketSecurityLevelNone] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6000014a58e0 -- thread:0x600001e6fbc0

220 ready for tls

WROTE Oct 18 23:33:53.642 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.planet-service.fr -- port:587 -- socket:0x600000ab43a0 -- thread:0x6080032654c0

EHLO [10.0.0.108]

READ Oct 18 23:33:53.698 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.planet-service.fr -- port:587 -- socket:0x600000ab43a0 -- thread:0x6080032654c0

250-smtp.planet-service.fr

250-AUTH LOGIN CRAM-MD5 PLAIN

250-AUTH=LOGIN CRAM-MD5 PLAIN

250-PIPELINING

250 8BITMIME

WROTE Oct 18 23:33:53.699 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.planet-service.fr -- port:587 -- socket:0x600000ab43a0 -- thread:0x6080032654c0

QUIT

WROTE Oct 18 23:33:53.777 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6000014a58e0 -- thread:0x600001e6fbc0

EHLO [10.0.0.108]

WROTE Oct 18 23:33:53.778 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6080010b1400 -- thread:0x600003479b00

EHLO [10.0.0.108]

READ Oct 18 23:33:53.838 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6000014a58e0 -- thread:0x600001e6fbc0

250-smtp.planet-service.fr

250-AUTH LOGIN CRAM-MD5 PLAIN

250-AUTH=LOGIN CRAM-MD5 PLAIN

250-PIPELINING

250 8BITMIME

WROTE Oct 18 23:33:53.838 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6000014a58e0 -- thread:0x600001e6fbc0

QUIT

READ Oct 18 23:33:53.842 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6080010b1400 -- thread:0x600003479b00

250-smtp.planet-service.fr

250-AUTH LOGIN CRAM-MD5 PLAIN

250-AUTH=LOGIN CRAM-MD5 PLAIN

250-PIPELINING

250 8BITMIME

WROTE Oct 18 23:33:53.843 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.planet-service.fr -- port:587 -- socket:0x6080010b1400 -- thread:0x600003479b00

QUIT

Yes, I can send emails when I uncheck "SSL" in the SMTP setting on my mac, but it's a work arround because it's better to send email with smtp.

I got the same answer, Apple shall fix the problem

Mine started working again after another restart.

I have the same problem. I think the problem is in yosemite

I have the same problem and when I change teh settings (for example, Inactivate the SSL) and close ando open again the mail, the settings are unchanged again.  The problem is yosemite

Try restarting your computer a couple of times if necessary. That's what fixed mine. Didn't have to uncheck SSL either.