IMAP SSL Certificate Errors

Just got my iPhone today.

My email server has a simple, self-signed SSL certificate (IMAPS and TLS on the MTA). The iPhone doesn't like this and refuses to work with my mail/imap server.

This won't work for me and I'm wondering if there is a way around this.

Thanks.

iPhone 8gb

Posted on Nov 11, 2007 8:06 PM

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Posted on Nov 15, 2007 11:01 AM

I had the same problem - using a self-signed SSL certificate on a Linux server running courier IMAP. This is how I got it working (some wording may not be exact due to my faulty memory):

1) Enter Mail on iphone
2) Select "Other..." from list of mail providers
3) Enter all account specifics
4) Click 'Save' - I get the invalid certificate error
5) Click "Cancel' - it returns to settings screen
6) Click "Save" again - it says "You may not be able to receive email..."
7) Click "Ok"
8) Display changes to mail window, loads my messages despite the warning.
12 replies
Question marked as Top-ranking reply

Nov 15, 2007 11:01 AM in response to Forrest

I had the same problem - using a self-signed SSL certificate on a Linux server running courier IMAP. This is how I got it working (some wording may not be exact due to my faulty memory):

1) Enter Mail on iphone
2) Select "Other..." from list of mail providers
3) Enter all account specifics
4) Click 'Save' - I get the invalid certificate error
5) Click "Cancel' - it returns to settings screen
6) Click "Save" again - it says "You may not be able to receive email..."
7) Click "Ok"
8) Display changes to mail window, loads my messages despite the warning.

Jan 19, 2008 1:26 PM in response to MQB

This was extremely helpful to me. Thanks. Basically it seems the iPhone assumes you want SSL turned on when doing IMAP, and it does not give you a way to turn if off until AFTER you have set up your mail. The advanced settings button does not even show up until AFTER you have the account saved, and every time you try to save it, you get error messages. So your steps below save the day, but I added a couple of more.

1) Enter Mail on iPhone
2) Select Other from the list of mail provider options
3) Enter all the Account specifics, in my case it was IMAP stuf
4) Click Save, and get the invalid certificate message
5) Click "CANCEL", an you get returned to the settings screen
6) Click "SAVE" again, it says, "You may not be able to receive email..."
7) Click OK
8) Now you can go back into the settings, and preso chango, the ADVANCED button now shows up at the bottom of the mail screen.
9) NOW you can go into the advance tab and turn OFF SSL for both sending and receiving mail.

What a pain, but it works.

Nov 13, 2007 5:48 AM in response to rh

I've just set up IMAP to a self-signed cert server and it warned about lack of trust but then worked just fine when choosing "continue". What version are you running? my setup's details below:

Server:
IMAP on 993, self signed cert, Windows 2003 w/ Exchange 2003 enterprise, fast imap enabled and show public folders in imap list enabled.

phone:
iPhone v1.1.1

Nov 14, 2007 3:20 AM in response to Nathan C

Not sure where you going with that analogy Nathan,

a digital certificate has an issuer, issued by a CA, and a FQDN against which it is issued. therefore you can have a certificate that is issued by an untrusted CA but for the correct FQDN or it can be issued by a trusted CA but against an FQDN different to the server address used by the client to reach the server, or it can be both.

So, the ID has either got your wife's name on it (wrong target name), or it's written in crayons (untrusted issuer), or both; either way the cops are going to stop you.

Going back to the other guy's problem - i'm using an untrusted CA but it's made out to the correct host name, this seems to work fine.

Nov 13, 2007 5:53 AM in response to Viking369

I'm using a 1.1.2 iPhone (in the UK). The server is on a Linux box, but not sure what exactly (hosted by dataflame.co.uk).

If I sync the account via iTunes, then the iPhone never gets passed the 'checking for new mail' stage. If I set up the account manually on the iPhone, then it warns me about the server but I just click continue, but then it just stays 'validating IMAP information' for ages and never completes this.

Maybe it just doesn't like my server, but Mail.app has no problem with it.

Cheers

Russell

Nov 13, 2007 9:31 AM in response to rh

Here is some debugging info from my server logs that may give hint as to what's going on. I do have SMTP AUTH configured (Sendmail), and things are working generally for anything else that connects. I'm certain I've typed my password in correctly, too (into the iPhone). The digest error makes me wonder what the iPhone is returning.



Nov 13 12:27:12 mail imaps[41530]: starttls: TLSv1 with cipher AES128-SHA (128/128 bits reused) no authentication

Nov 13 12:27:14 mail imaps[41530]: starttls: TLSv1 with cipher AES128-SHA (128/128 bits reused) no authentication

Nov 13 12:27:14 mail imaps[41530]: badlogin: host.name.com [xx.xx.xx.xx] DIGEST-MD5 [SASL(-13): authentication failure: client response doesn't match what we generated]

Nov 13 12:27:17 mail imaps[41530]: starttls: TLSv1 with cipher AES128-SHA (128/128 bits reused) no authentication

Nov 13 12:27:18 mail imaps[41530]: badlogin: host.name.com [xx.xx.xx.xx] CRAM-MD5 [SASL(-13): authentication failure: incorrect digest response]

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IMAP SSL Certificate Errors

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