TLS usage in Mail

I've set up a postfix server using version 2.3.3 (redhat) along with dovecot.
Enabled it to use TLS. The previous version of postfix was 2.2.x. Mail worked just fine
using TLS on version 2.2. It breaks when using the newer version with TLS. Secure pop3
or secure imap works just fine with Mail and dovecot. It's smtp using TLS that has a problem.
Turning off TLS and using port 25 works just fine.
Loaded up Thunderbird and ran the checks SSL, TLS, text (port 25, plain vanilla), same certificates
as used with mail. Works just fine.
Ran same checks using Mail, and turned debug on at the mail server (postfix), and it looks like
it hangs during the TLS negotiation. i.e. does not handle version 3 it seems. It hung on the client
side, i.e. Mail.
Checked using ports 25, 465, and 587. Tried unchecking SSL at Mail for port 587.
No affect. Mail autochecks the connection, and sometimes it would pass, and other times
it would fail. This depended entirely on the server side (postfix) cached credentials. Turning
caching off at the postfix server provides a better test of the way Mail works.
i.e. in postfix comment out the line "smtpdtls_session_cachedatabase = "in main.cf ,
also setting the "smtpdtls_session_cachetimeout = " to a low value works.
The CA used for all checks was self signed. It was used to sign the server certificate.
This worked just fine for all clients and servers involved.
Here is what the server (postfix) log is indicating when the port is 587 and SSL check box is
checked using plain username and password to authenticate.
Feb 6 17:51:38 mail postfix/smtpd[9565]: connect from crystal.pharmacy.ohio-state.edu[128.146.80.58]
Feb 6 17:51:38 mail postfix/smtpd[9565]: disconnect from crystal.pharmacy.ohio-state.edu[128.146.80.58]
Feb 6 17:51:49 mail postfix/smtpd[9565]: connect from crystal.pharmacy.ohio-state.edu[128.146.80.58]
Feb 6 17:51:49 mail postfix/smtpd[9567]: initializing the server-side TLS engine
Feb 6 17:51:49 mail postfix/smtpd[9565]: setting up TLS connection from crystal.pharmacy.ohio-state.edu[128.146.80.58]
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:before/accept initialization
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:error in SSLv2/v3 read client hello A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:error in SSLv3 read client hello B
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:error in SSLv3 read client hello B
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 read client hello B
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 write server hello A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 write certificate A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 write server done A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 flush data
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:error in SSLv3 read client certificate A
Feb 6 17:51:49 mail postfix/smtpd[9567]: connect from crystal.pharmacy.ohio-state.edu[128.146.80.58]
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:error in SSLv3 read client certificate A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 read client key exchange A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:error in SSLv3 read certificate verify A
Feb 6 17:51:49 mail postfix/smtpd[9567]: setting up TLS connection from crystal.pharmacy.ohio-state.edu[128.146.80.58]
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:before/accept initialization
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:error in SSLv2/v3 read client hello A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:error in SSLv3 read client hello B
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:error in SSLv3 read client hello B
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 read client hello B
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 write server hello A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 write certificate A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 write server done A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 flush data
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:error in SSLv3 read client certificate A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:error in SSLv3 read client certificate A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 read client key exchange A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:error in SSLv3 read certificate verify A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:error in SSLv3 read certificate verify A
Feb 6 17:51:49 mail last message repeated 2 times
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 read finished A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 write change cipher spec A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 write finished A
Feb 6 17:51:49 mail postfix/smtpd[9565]: SSL_accept:SSLv3 flush data
Feb 6 17:51:49 mail postfix/smtpd[9565]: save session FDE39063436627C13B70FC2F99018D62FD617A52D02330C71BC11BE36BC0090A to smtpd cache
Feb 6 17:51:49 mail postfix/tlsmgr[9566]: put smtpd session id=FDE39063436627C13B70FC2F99018D62FD617A52D02330C71BC11BE36BC0090A [data 126 bytes]
Feb 6 17:51:49 mail postfix/tlsmgr[9566]: write smtpd TLS cache entry FDE39063436627C13B70FC2F99018D62FD617A52D02330C71BC11BE36BC0090A: time=1233960709 [data 126 bytes]
Feb 6 17:51:49 mail postfix/smtpd[9565]: TLS connection established from crystal.pharmacy.ohio-state.edu[128.146.80.58]: TLSv1 with cipher AES128-SHA (128/128 bits)
Feb 6 17:51:49 mail postfix/smtpd[9565]: disconnect from crystal.pharmacy.ohio-state.edu[128.146.80.58]
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:error in SSLv3 read certificate verify A
Feb 6 17:51:49 mail last message repeated 2 times
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 read finished A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 write change cipher spec A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 write finished A
Feb 6 17:51:49 mail postfix/smtpd[9567]: SSL_accept:SSLv3 flush data
Feb 6 17:51:49 mail postfix/smtpd[9567]: save session C45CE103ACA91E9BE220A32CA1007F7C61601DCFE753A08EF726DAE1ED166731 to smtpd cache
Feb 6 17:51:49 mail postfix/tlsmgr[9566]: put smtpd session id=C45CE103ACA91E9BE220A32CA1007F7C61601DCFE753A08EF726DAE1ED166731 [data 126 bytes]
Feb 6 17:51:49 mail postfix/tlsmgr[9566]: write smtpd TLS cache entry C45CE103ACA91E9BE220A32CA1007F7C61601DCFE753A08EF726DAE1ED166731: time=1233960709 [data 126 bytes]
Feb 6 17:51:49 mail postfix/smtpd[9567]: TLS connection established from crystal.pharmacy.ohio-state.edu[128.146.80.58]: TLSv1 with cipher AES128-SHA (128/128 bits)
Feb 6 17:51:49 mail postfix/smtpd[9567]: disconnect from crystal.pharmacy.ohio-state.edu[128.146.80.58]
However, the Mail application indicates that the outgoing server is (offline).
It maintains this message for port 465 for all configurations as well.
Doesn't work any better on port 25 for any of the secure configurations.
Question: Does an exception for Mail have to be entered into the postfix server policy for the
security level (v 1, 2, or 3, or TLS v1) supported by the Mail application?
Question: Does Mail application support TLS as implemented by the current version of SSL and
Postfix?
Thank you for considering this problem.
Ed Beranek

I have discovered somthing odd.
My network was setup using a single Dlink DI-524 router sharing a 10M down / 1M up connection to a Nintendo Wii, Linux server, and 3 Windows XP pcs and my single Macbook. I noticed through the logs that the Wii connected multiple times through the wifi connection getting updates and every time that it did this it would temporarily knock my Macbook off the network causing a delay accessing Gmail's IMAP servers. This causes Mail.app to go into a loop trying to access the IMAP servers and chew up tons and tons of RAM.
Solution. I setup a second Belkin router off one of my Dlink's ports and configured it to only allow my Macbook and AppleTV to access it. Problem solved. I have a rock solid internet connection with zero disruption to Gmail's IMAP servers. It appears with the 10.5.2 update, mail.app has developed a sensitivity to how it connects to the network. Hopefully 10.5.3 fixes it. We will have to see.
Hope this helps.

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which are the risks to disable TLS on outbound mail ?
I should do that because of corporate mail filtering purposes and with TLS is is impossible to scan mail and/or attachments
Any help appreciated.
Best regards.

SMTP over TLS should not affect your ability to scan mail or attachments. The TLS happens in transit between SMTP gateways.
Twitter!:
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Hi, thanks for reply.
Can you please explain ?
However, If I try to scan smtp protocol with my appliance, it does not work: error is that traffic is encrypted.

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The Scenario for the interface is IDOC to Mail.
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Usage says mail app 2.4GB

I'm using an ipad2 with Os 7.1.1 I think.
OF course 32GB is not enough and am trying to free up space.
Under the settings tab - usage it lists all of your apps and how much room they require. The biggest one is mail, 2.4GB
I have deleted every email on all three accounts I have (bulk deleting email was a doozy btw) and the program still takes up 2.4GB
HOw do I gain back memory. There is no way mail is that memory intensive.
thanks in advance for your assistance

I have discovered somthing odd.
My network was setup using a single Dlink DI-524 router sharing a 10M down / 1M up connection to a Nintendo Wii, Linux server, and 3 Windows XP pcs and my single Macbook. I noticed through the logs that the Wii connected multiple times through the wifi connection getting updates and every time that it did this it would temporarily knock my Macbook off the network causing a delay accessing Gmail's IMAP servers. This causes Mail.app to go into a loop trying to access the IMAP servers and chew up tons and tons of RAM.
Solution. I setup a second Belkin router off one of my Dlink's ports and configured it to only allow my Macbook and AppleTV to access it. Problem solved. I have a rock solid internet connection with zero disruption to Gmail's IMAP servers. It appears with the 10.5.2 update, mail.app has developed a sensitivity to how it connects to the network. Hopefully 10.5.3 fixes it. We will have to see.
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Where is the TLS option in Mail?

Hello,
I keep seeing thing on the net indicating that Mail supports TSL, yet I can't find the setting anywhere.
Thanks,
-Travis

Ah, nope, it works in Thunderbird. It is definitely a problem with Apple Mail.
I haven't seen million of Mail users work, you are the only one who claimed it... so would you be glad to show what does one need to do in order to make Mail work?
And yes I have tried the Google documentation, Mail just refuse to work... that's why I Google about this and found this thread.
EDIT:
Here's the SMTP setting I have in Mail: (Mail - Preferences - Accounts - Outgoing Mail Server)
Description: Google
Server Name: smtp.gmail.com
Use Custom Port: 465
User SSL: Checked
Authentication: Passoword
User Name: [email protected]
Password: *****
I also have tried the same thing with port 587 and port 25. And yes I have verified that I have the correct username and password.
In "connection doctor" it said that it "Could not connect to this SMTP server", "check your connection", "if the SMTP server doesn't support SSL then uncheck SSL".
Of course there are nothing wrong with my connection, because thunderbird works. But again thunderbird explicitly stated that it will try TLS then SSL.
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Bt usage e mail !

i have been on option 3 for over a year now and after a few phone calls to cancellations over the past few days renewed my contract today (wednesday). i have just got home and found an e mail saying i have gone over my option 2 broadband limit !! and when i log into my account it says im on opption 3 still but then check my usage and it says i am 11 gb over my 40gb limit !
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you need to contact the mods for assistance http://bt.custhelp.com/app/contact_email/c/4951
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High CPU usage in Mail

I know that this topic has been discussed before, without any real cause being identified (as far as I can see). I have a specific question (at the end of the post).
I am a light Mail user, with one POP account and I don't use to-dos, MobileMe, or anything other than simple sending and receiving of emails - no more than half a dozen per day. I leave mail open in the background, sending requests for new messages every 5 minutes
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This certainly happened with 10.5.3 as well as 10.5.4 - I can't remember whether it was a problem with 10.5.2. It certainly wasn't with 10.3.x.
I wonder whether my Mail data has become damaged or corrupted in any way. So my question is: Is there any mechanism to rebuild or check the sanity of the Mail data, similar to what is available in iPhoto?
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Tls usage requirements

Hi,
i can successfuly connect my spa504g to a kamailio server and get mwi notifications using UDP.
when i use tls, i successfuly register in the the server and also subscribe to mwi events.
i can make calls and srtp also works.
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do i have to create a mini certificate and configure it in spa50g for tls mwi notifications to work ?
i don't know if the problm is with the server or with misconfiguration in spa504g.
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thank you

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my Iphone 5 has mail usage at 7.2KB. I have no mail in mail box. Why is it taking up so much space? My IPAD has 10,000 message and my usage for mail there is 535 MB, What's wrong with my Iphone 5? Thanks

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TLS problems with OIM mailing through exchange server

Dear All,
I ran into a problem concerning the internal mailing mechanism Oracle provides in OIM.
Im trying to send email definitions through a custom made mail adapter.
Each time i send it i get a 530 5.7.1. Client was not authenticated error.
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When we turn TLS off the mails are being sent but when it it turned on again the error returns.
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Hello,
After updating to Mavericks (from Mountain Lion), I noticed that there's a new keychain called "local items" inside Keychain Access App.
so I have a couple of questions regarding this and my usage of Mail:
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2) now, I noticed that the passwords that I typed in for my e-mail accounts (set up in Apple's Mail) are saved inside this "local items" keychain. So everything seems to be fine. However, I noticed that the passwords saved inside this "local items" keychain cannot be edited in the "access control" panel (this is accessed by double clicking the password item and click on the "access control" tab.) This is odd because all the other items in the "login" keychain can be edited in this way.
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so a recap/summary:
my login and local items keychain sync up fine
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I want to make Mail use another keychain (i.e. a keychain I set up myself), can we possible to this?
or another other work around that will make Mail to prompt me to enter passwords when I fire up the application (not constantly, but just when I restarting the application, OR after the computer wakes up)
I'd appreciate any pointers!
thank you very much!
sakura

I have the same concerns. I'm frustrated that the Mail app doesn't currently allow you to use a separate keychain for the passwords. After many years with Keychain I am being tempted to look to a third party. Or perhaps it's time to look for a third party mail app? This is a security issue since email is the primary way that a password change is verified with other accounts.

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