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Can't connect to SMTP using TLS with Self-Signed Certificate on OSX 10.10.1 (T31.3 & 24.6)

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  • 2 have this problem
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  • Last reply by Matt

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I can't connect to my SMTP server using TLS on ports (Send 465 or 587/ Receive 995) using Thunderbird 31.3 or 24.6 from my OS X 10.10.1 (Yosimite) MacBook Pro.

However, I am able to send and receive mail from/to the same account on my Window 7 machine using Outlook 2007, using the same settings as I've configured in Thunderbird. I've added the certificate etc.

http://img.photobucket.com/albums/v631/Napoleon_BlownApart/ScreenShot2014-12-16at121323pm.png (Taken while using 24.6)

I am the server admin and the password and other server side settings are correct! (I'm going to have a look at Evolution in the mean time. I've already reverted to an earlier Firefox version due to sloppy coding and broken features.)

Any ideas?

I can't connect to my SMTP server using TLS on ports (Send 465 or 587/ Receive 995) using Thunderbird 31.3 or 24.6 from my OS X 10.10.1 (Yosimite) MacBook Pro. However, I am able to send and receive mail from/to the same account on my Window 7 machine using Outlook 2007, using the same settings as I've configured in Thunderbird. I've added the certificate etc. http://img.photobucket.com/albums/v631/Napoleon_BlownApart/ScreenShot2014-12-16at121323pm.png (Taken while using 24.6) I am the server admin and the password and other server side settings are correct! (I'm going to have a look at Evolution in the mean time. I've already reverted to an earlier Firefox version due to sloppy coding and broken features.) Any ideas?

Chosen solution

If the server name is secret, how do you expect it to receive mail. Please we have enough trouble without guessing. Seriously what are you doing using a self signed certificate, they are free from here https://www.startssl.com/

My guess is it is OSX that does not like the self signed certificate, how does Thunderbird cope under windows. As you have a copy install Thunderbird and see if it is an OSX issue.

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Chosen Solution

If the server name is secret, how do you expect it to receive mail. Please we have enough trouble without guessing. Seriously what are you doing using a self signed certificate, they are free from here https://www.startssl.com/

My guess is it is OSX that does not like the self signed certificate, how does Thunderbird cope under windows. As you have a copy install Thunderbird and see if it is an OSX issue.

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@Matt, I tried Thunderbird on Win7, being in Australia, it was the British version.

My most humble apology!!!! The password was in fact wrong. A 'l' (lowercase L) looked like the number '1' in the Times New Roman font I'm using on Windows. Perhaps it's time to get glasses?


The server name is not secret, its just that I always block out that kind of info (names, domains & IPs etc).

Concerning SSL certificates, nothing is free in this world, so the question is what is the price? Personally I'm waiting for the EFF initiative to come into being in the next month or so.

Cheers, Nap

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I got my glasses and I still can not see.... Look a right git trying to read wifi passwords on the bottoms of new routers, and don't get me started on the almost impossible to read color scheme of this web site (pale blue on grey and in places grey on grey) sao no apology needed when it copes to being blind

Personally I use start, price is they want to know who i am, and the free ones are only valid for 12 months. Being in Israel makes me feel a little better than all the US based providers by about a hair. If about the width a a hair can be used to measure better.

But any separation from US law is good in my opinion if only by "that much". Net neutrality is entirely dependent on having bits in lots of jurisdictions so one lot can not dictate. Be it MOSAD, NSA MI6 or our own collection is black hats ASIS and ASIO