Cannot make a secure SSL connection

The warning text is actually a recent change handling a problem where some servers offered SSL connection on port 993, but where it didn't work on port 143 (the recommended IMAP port). This looks like it could be a bug related to this change (or a very strange server).

What is the server address? (Allows me to connect on ports and see how the IMAP server responds before authentication.)

There is no way to adjust the behavior (other than changing port/ssl settings). I'll consider it a bug in MailMate for now.

The server details can be found here: http://help.runbox.com/email-client-settings/

You might need to wait for a while to see the problem. Sometimes it goes for hours without the dialogue but, once it starts, several notifications come one after the other.

More specifically:

Incoming Server (IMAP): secure.runbox.com
Port: 993
SSL: Yes
Authentication: Password
IMAP Prefix: INBOX

Thanks Benny!

To save you some time, here's an excerpt from the Activity Viewer showing the segment where the errors occur:

Trying to disconnect nicely...
C: R15 LOGOUT
S: * BYE Courier-IMAP server shutting down
S: R15 OK LOGOUT completed
Clearing connection to secure.runbox.com
Synchronizing mailbox (attempting to do it quickly): INBOX/Archive
Selecting mailbox: INBOX/Archive
Clearing connection to secure.runbox.com
Trying to connect to secure.runbox.com on port 993
Successful connection.
Initiating SSL/TLS...
Error: Failed SSL handshake.
Clearing connection to secure.runbox.com
Synchronizing mailbox (attempting to do it quickly): INBOX/Archive
Selecting mailbox: INBOX/Archive
Clearing connection to secure.runbox.com
Trying to connect to secure.runbox.com on port 993
Successful connection.
Initiating SSL/TLS...
Error: Failed SSL handshake.
Clearing connection to secure.runbox.com
Synchronizing mailbox (attempting to do it quickly): INBOX/Archive
Selecting mailbox: INBOX/Archive
Clearing connection to secure.runbox.com
Trying to connect to secure.runbox.com on port 993
Successful connection.
Initiating SSL/TLS...
Error: Failed SSL handshake.
Clearing connection to secure.runbox.com
Synchronizing mailbox (attempting to do it quickly): INBOX/AOL Incoming
Selecting mailbox: INBOX/AOL Incoming
Clearing connection to secure.runbox.com
Trying to connect to secure.runbox.com on port 993
Successful connection.
Initiating SSL/TLS...
Setup of SSL/TLS connection complete.
S: * OK [CAPABILITY IMAP4rev1 UIDPLUS CHILDREN NAMESPACE THREAD=ORDEREDSUBJECT THREAD=REFERENCES SORT QUOTA IDLE] perdition ready on mailfront04.runbox.com 0002aa86
C: D0 LOGIN ••••••••••
S: D0 OK LOGIN Ok.

Thanks for the log. I'm not sure it helps much.

I found a bug though. The wrong port number is displayed in the error, but if you have fixed the port number to 993 then it shouldn't matter.

And the server does have the problem that port 143 does not allow STARTTLS (secure connection). Are you sure the settings explicitly use port 993. Maybe do a restart after that to make sure MailMate doesn't cache an old port number (that might happen when retrying after an error).

I restarted MailMate a couple of times, but will do it again now just in case.

I think the settings are fine. Here's a screenshot of the relevant part:

http://02b.me/mbQ8/4Zg9k3IP

Yes, those settings should force port 993 to be used. Let me know when
it happens again.

Just happened again. The dialog came up twice when I was away from the keyboard for a short while. The screen was unlocked and the computer is set to not sleep, by the way.

As I mentioned, it seems to happen more often when the computer is not actively used.

I'm running in OS X 10.9 and thought that perhaps the App Nap new feature was causing it. I turned it off for MailMate but it seems to have no effect in preventing the issue.

Apple Mail and the iOS mail client (both iPhone and iPad) don't seem to have a problem with this server. I was able to get a connection while MailMate was having troubles.

Ok, it does sound like a MailMate bug. I've fixed the error message
issue and when I have a test version out with this fix then I'd like you
to try again. I'd like to know if the issue is really with port 993 or
if MailMate is (wrongly) also trying to connect on port 143 (probably
when 993 fails, e.g., because of a connection timeout). I think the
latter is most likely (I'll take another look at the code).

Thanks Benny!

I'll switch to Apple Mail meanwhile and give it another try when you have the new version.

Hold down ⌥ when clicking “Check Now” in the Software Update preferences pane. That should provide you with r3802 which fixes the error message. See if that reports a different port number.

Installed the new version. MailMate asked to rebuild the database (not sure if related or something else).

After a while when the computer was idle, I got a few failed handshake messages like this:

http://02b.me/GBn1/51a0IJfc

An excerpt of the Activity Viewer errors looks like this:

Clearing connection to secure.runbox.com Synchronizing mailbox (attempting to do it quickly): INBOX/Apple Mail To Do Selecting mailbox: INBOX/Apple Mail To Do Clearing connection to secure.runbox.com Trying to connect to secure.runbox.com on port 993 Successful connection. Initiating SSL/TLS... Error: Failed SSL handshake. Clearing connection to secure.runbox.com Synchronizing mailbox (attempting to do it quickly): INBOX/AOL Legacy Selecting mailbox: INBOX/AOL Legacy Clearing connection to secure.runbox.com Trying to connect to secure.runbox.com on port 993 Successful connection. Initiating SSL/TLS... Setup of SSL/TLS connection complete.

So, it's reporting failures in 993 from what I understand.
By the way, the service causing problems has a free trial period in case you want to test it yourself. The logs I get don't give much detail other than the "failed handshake" part.

A database rebuild should be quite rare. If it happens again I'm very interested in the error reported.

It seems the problem has changed. The “Failed SSL handshake” error is different than “Cannot make secure...” error. I have another user with the “Failed SSL handshake” problem. It's not the same server though.

I think I've had a runbox account in the past. I'll see if I still have access or if I can create a new one.

Ok, I've created a runbox account. So far, no problems, but I'll leave it online and see what happens.

Just for the record:

Trying to connect to secure.runbox.com on port 993  
Successful connection.  
Initiating SSL/TLS...  
Setup of SSL/TLS connection complete.  
S: * OK [CAPABILITY IMAP4rev1 UIDPLUS CHILDREN NAMESPACE THREAD=ORDEREDSUBJECT THREAD=REFERENCES SORT QUOTA IDLE] perdition ready on mailfront02.runbox.com 0002aa84

The database rebuild was related to some inconsistency in the mailboxes, if I remember. I told MailMate to rebuild from the server data and it did so without problems. I wish I had a screenshot of the error but it didn't occur to me to take one.

As I mentioned, the failed handshakes seem to happen when I'm away from the keyboard on using an app that doesn't require input (watching movies in full screen in iTunes, for instance). Maybe it's just a timing issue between the client and the server, or some server limit on the rate of requests. MailMate succeeds in connecting most of the time, at least while I'm actively typing…

I'm enjoying MailMate and would keep it open full time if not for those annoying error dialogs.

Thanks again. :-)

We'll see if I have issues with my test account.

It also seems Runbox is in the process of changing how their servers behave: http://www.emaildiscussions.com/showthread.php?t=67296

Note that you can probably use port 143 without SSL if that is not a big problem for you (depends on the sensitivity of the content of your emails).

I just got a few more of those handshake errors while away. When I ask MailMate to retry it usually goes through the second or third time:

http://02b.me/6pOk/BaUC7Unj
http://02b.me/g0If/5inJZSl9

I would rather keep on the secure ports as I often use email on public networks. Nothing sensitive but why broadcast info to people I don't know? :)

Although a good provider, Runbox is pretty slow in implementing things. I wouldn't hold my breath on the server changes. I'll believe it when it's done. ;)

Benny,

As an update, I'm still seeing the handshake error dialogues and was wondering if you were able to replicate the problem.

Thanks!

I have a Runbox test account, but I haven't seen this issue yet. My trial period is 3 more weeks. I'll leave it online. If you see any pattern leading up to the errors then let me know.

Hello! New mailmate user from recent indiegogo campaign and really liking it BUT i'm having this same runbox error. It's not a dealbreaker but it is annoying. Also using secure connection and would prefer to keep it that way. Haven't had an issue in any other clients as well...

-b

@brandon: I've seen the issue once with my test account, but the problem disappeared again immediately. How often does this happen for you? How quickly does the problem resolve itself?

(The only possible workaround I can think of at the moment is to retry more and wait longer before reporting the issue to the user.)

generally happens maybe twice a day with several folders in the account. If I hit retry that's generally all it will take but I'll get a string of folders at a time (4-5). Hasn't happened yet today and have been on since 8:30am (it's 1pm my time).

-brandon

@brandon: Ok, that sounds like I may be able to resolve it by being better at delaying retries before reporting a problem. I'll look into it (when I get time, busy days). I'll update this ticket if I've changed something.

Just to add a few more details:

I have 17 folders (mailboxes) inside my Runbox account. The problem occurs with different folders each time. Usually 2-3 of them report failures and the others connect without a problem.

It's possible to minimize the error dialogues by reducing the frequency of synchronization for each folder. I set the ones that are less important to sync either manually or every hour. Even doing that, it gets annoying after a while.

Benny, perhaps you are not seeing the errors because you have a simpler structure in your account?

I'm hoping a solution can be found as it's hard to switch Apple Mail after using MailMate…

Thanks! :-)

Hold down ⌥ when clicking “Check Now” in the Software Update preferences pane. This is r3839 with an attempt to fix your issue or at least decrease the nuisance.

And yes, it might be because I have fewer mailboxes.

Thanks, Benny! :-)

Will let it run for a week and see how it goes.

Thanks! I'm doing the same!

No errors so far. I've been traveling and only had a couple of days to test it, but seems to be working. I left MailMate open overnight and the previous error windows haven't popped up yet.

Thanks, Benny! :-)