OSX Mail app won't send

[$m@Rt@$$]

Alright, so I use the stock mail app that comes with OSX. I've been told that I like to live dangerously.

So I have my personal Gmail account and IMAP based work email addresses loaded on there. Gmail works 100% but the IMAP simply won't send mail. I always get an error a couple of minutes after sending when it just sits in my outbox. However under the exactly same settings it too works 100% on my iPhone.

I haz no idea what's going on.

 

[creeper]

Run the connection doctor and see what happens.

 

[$m@Rt@$$]

Run the connection doctor and see what happens.

So this is what it does.

 

[creeper]

Darn. Don't have my MBP with me. You need to change the default outgoing server to the google SMTP server. That setting hides away somewhere in the system preferences.

 

[GreGorGy]

Your ISP could be blocking SMTP access - mweb does that, for instance - to other providers.

 

[$m@Rt@$$]

Your ISP could be blocking SMTP access - mweb does that, for instance - to other providers.

Everyone else's is working fine at the office. And it does this everywhere. I don't think this is an ISP issue.

 

[$m@Rt@$$]

Darn. Don't have my MBP with me. You need to change the default outgoing server to the google SMTP server. That setting hides away somewhere in the system preferences.

Change the work address SMTP to google's?

 

[SauRoNZA]

Have you got 2-stage Authentication enabled?

 

[$m@Rt@$$]

Have you got 2-stage Authentication enabled?

Gmail is working fine. Its my work email is isn't sending out mail.

 

[SauRoNZA]

Okay I'm with you now.

Then read what the error is saying, seems you are trying to send mail over port 993 (which is the common Gmail settings but probably not your work mail's).

So go Preferences > Account > SMPT Dropdown > Edit SMTP List

Click advanced and change the port to "587" instead.

 

[SauRoNZA]

You might need to also disable TLS (set to None) on the Account information tab next to Advanced.

 

[$m@Rt@$$]

Okay I'm with you now.

Then read what the error is saying, seems you are trying to send mail over port 993 (which is the common Gmail settings but probably not your work mail's).

So go Preferences > Account > SMPT Dropdown > Edit SMTP List

Click advanced and change the port to "587" instead.

That is what my iPhone defaulted to and it's working fine on there. Changing the port to 587 makes it error immediately

 

[SauRoNZA]

Okay let's forget your iPhone for a moment, unless it's on the same network (wireless) and not using 3G then it's not applicable.

Did you switch TLS to none?

With TLS off you can also try Port 25.


If you must use TLS try using Port 465.

 

[$m@Rt@$$]

It always on the same wifi, that's why I'm saying

TLS is switched to none. I'll give those a go.

Okay, so I turned on TLS and set it to use default ports (25, 465 and 587 I think). And for some weird reason it's working :wtf:

Thanks @SauRoNZA

 

[SauRoNZA]

LOL that's a bit odd.

TLS shouldn't work on 25 and 587 but if it solved the problem then it solved the problem.

Exchange server I'm guessing?

 

[$m@Rt@$$]

LOL that's a bit odd.

TLS shouldn't work on 25 and 587 but if it solved the problem then it solved the problem.

Exchange server I'm guessing?

I think so yeah

 

[$m@Rt@$$]

Well this is happening all over again. Mail works 100% on iPhone but it won't send once again with my Mac. Connection doctor says it successfully connects with the IMAP and SMTP of our exchange server.

What gives...

 

[GreGorGy]

Well this is happening all over again. Mail works 100% on iPhone but it won't send once again with my Mac. Connection doctor says it successfully connects with the IMAP and SMTP of our exchange server.

What gives...

EXACTLY a month later. Try the same process as previously, perhaps in reverse.

 

[$m@Rt@$$]

I have, but what is above my mind is the fact that I haven't changed a single setting. How is that even possible. SIGH.