Using StartTLS with IMAP connection to Exchange is giving me different certificates for machines different to the IMAP server, security exception each time

I'm using Thunderbird with my work email account, which is using Exchange, this is not officially supported but access is allowed via IMAP.
The problem is when I'm using StartTLS or SSL I'm getting multiple different self signed certificates being returned, seeming depending on which specific backend server is handling the request, each time it causes the Confirm Security Exception dialog to be displayed. If I confirm the exception I get the dialog being displayed again until eventually I get a certificate that seems to match the first certificate I confirmed, at which point I can download or send my pending mail.
Thus is seems that there is only one certificate being stored as an exception for each server connection. Is there some way round this?
Thanks.

What is the reason for the exception prompt in the first place?

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itauthority.co.uk |
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Dear all,
I am having problems with exchange 2010 sending emails through a postfix smarthost server which disconnects the sessions. I also use a sendmail as a smarthost
server which is working just fine but I have to switch to postfix and cannot do this as long as the encryption does not work.
Here is the log file of the postfix server:
Jan 4 14:18:59 server7 postfix/smtpd[1659]: initializing the server-side TLS engine
Jan 4 14:18:59 server7 postfix/smtpd[1659]: connect from server1.mydomain.com[192.168.20.10]
Jan 4 14:18:59 server7 postfix/smtpd[1659]: setting up TLS connection from server1.mydomain.com[192.168.20.10]
Jan 4 14:18:59 server7 postfix/smtpd[1659]: server1.mydomain.com[192.168.20.10]: TLS cipher list "aNULL:-aNULL:ALL:+RC4:@STRENGTH"
Jan 4 14:18:59 server7 postfix/smtpd[1659]: SSL_accept:before/accept initialization
Jan 4 14:18:59 server7 postfix/smtpd[1659]: read from 7F4823FA5210 [7F4823FAB1B0] (11 bytes => -1 (0xFFFFFFFFFFFFFFFF))
Jan 4 14:18:59 server7 postfix/smtpd[1659]: read from 7F4823FA5210 [7F4823FAB1B0] (11 bytes => 11 (0xB))
Jan 4 14:18:59 server7 postfix/smtpd[1659]: 0000 16 03 01 00 5a 01 00 00|56 03 01 ....Z... V..
Jan 4 14:18:59 server7 postfix/smtpd[1659]: read from 7F4823FA5210 [7F4823FAB1BE] (84 bytes => 84 (0x54))
Jan 4 14:18:59 server7 postfix/smtpd[1659]: 0000 54 a9 3d b9 0d 5e 8b 64|7c 6b b5 21 f2 93 e7 84 T.=..^.d |k.!....
Jan 4 14:18:59 server7 postfix/smtpd[1659]: 0010 17 ea 33 d7 e5 13 f2 75|3a 87 38 32 01 85 82 5b ..3....u :.82...[
Jan 4 14:18:59 server7 postfix/smtpd[1659]: 0020 00 00 18 00 2f 00 35 00|05 00 0a c0 13 c0 14 c0 ..../.5. ........
Jan 4 14:18:59 server7 postfix/smtpd[1659]: 0030 09 c0 0a 00 32 00 38 00|13 00 04 01 00 00 15 ff ....2.8. ........
Jan 4 14:18:59 server7 postfix/smtpd[1659]: 0040 01 00 01 00 00 0a 00 06|00 04 00 17 00 18 00 0b ........ ........
Jan 4 14:18:59 server7 postfix/smtpd[1659]: 0050 00 02 01 ...
Jan 4 14:18:59 server7 postfix/smtpd[1659]: 0053 - <SPACES/NULLS>
Jan 4 14:18:59 server7 postfix/smtpd[1659]: SSL_accept:SSLv3 read client hello A
Jan 4 14:18:59 server7 postfix/smtpd[1659]: SSL_accept:SSLv3 write server hello A
Jan 4 14:18:59 server7 postfix/smtpd[1659]: SSL_accept:SSLv3 write certificate A
Jan 4 14:18:59 server7 postfix/smtpd[1659]: SSL_accept:SSLv3 write key exchange A
Jan 4 14:18:59 server7 postfix/smtpd[1659]: SSL_accept:SSLv3 write server done A
Jan 4 14:18:59 server7 postfix/smtpd[1659]: write to 7F4823FA5210 [7F4823FB8B70] (1911 bytes => 1911 (0x777))
Jan 4 14:18:59 server7 postfix/smtpd[1659]: 0774 - <SPACES/NULLS>
Jan 4 14:18:59 server7 postfix/smtpd[1659]: SSL_accept:SSLv3 flush data
Jan 4 14:18:59 server7 postfix/smtpd[1659]: read from 7F4823FA5210 [7F4823FAC803] (5 bytes => 0 (0x0))
Jan 4 14:18:59 server7 postfix/smtpd[1659]: SSL_accept:failed in SSLv3 read client certificate A
Jan 4 14:18:59 server7 postfix/smtpd[1659]: SSL_accept error from server1.mydomain.com[192.168.20.10]: lost connection
Jan 4 14:18:59 server7 postfix/smtpd[1659]: lost connection after STARTTLS from server1.mydomain.com[192.168.20.10]
Jan 4 14:18:59 server7 postfix/smtpd[1659]: disconnect from server1.mydomain.com[192.168.20.10]
I
have read in the post at https://social.technet.microsoft.com/Forums/exchange/en-US/6db38364-cb08-45c0-b159-3ddf30ef0b3e/exchange-2010-send-connector-uses-ssltls-and-cannot-connect-to-smarthost-how-to-deactivate-ssl?forum=exchange2010
how to deactivate the SSL encryption, but this is of course a security flaw, if I am not mistaken. I would like to encrypt the connection between the servers for obvious security
reasons but I have come to a standstill...
My Exchange server certificate is configured
as follows:
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAcc
ule, System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKe
essRule}
CertificateDomains : {server1, server1.solid-con.com}
HasPrivateKey : True
IsSelfSigned : True
Issuer : CN=server1
NotAfter : 22/01/2017 13:18:02
NotBefore : 22/01/2012 13:18:02
PublicKeySize : 2048
RootCAType : None
SerialNumber : 6925D91285B649BD4D5E4297F1A48471
Services : IMAP, POP, IIS, SMTP
Status : Valid
Subject : CN=server1
Thumbprint : 939A37173BF84E352CEDC74F7D9A3D71F498A005
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAcc
ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {WMSvc-SERVER1}
HasPrivateKey : True
IsSelfSigned : True
Issuer : CN=WMSvc-SERVER1
NotAfter : 19/01/2022 12:56:44
NotBefore : 22/01/2012 12:56:44
PublicKeySize : 2048
RootCAType : Registry
SerialNumber : 1DB8711F7ADC5CB54196468EF2FF5D21
Services : None
Status : Valid
Subject : CN=WMSvc-SERVER1
Thumbprint : 191D86BDE274510453D58DDB91D253DABBCF05F1
And My Default Send Connector is configured as follows:
AddressSpaces : {SMTP:*;1}
AuthenticationCredential : System.Management.Automation.PSCredential
Comment :
ConnectedDomains : {}
ConnectionInactivityTimeOut : 00:10:00
DNSRoutingEnabled : False
DomainSecureEnabled : False
Enabled : True
ErrorPolicies : Default
ForceHELO : False
Fqdn :
HomeMTA : Microsoft MTA
HomeMtaServerId : SERVER1
Identity : Internet
IgnoreSTARTTLS : False
IsScopedConnector : False
IsSmtpConnector : True
LinkedReceiveConnector :
MaxMessageSize : unlimited
Name : Internet
Port : 25
ProtocolLoggingLevel : None
RequireOorg : False
RequireTLS : False
SmartHostAuthMechanism : None
SmartHosts : {server7.mydomain.com, server6.mydomain.com}
SmartHostsString : server7.mydomain.com,server6.mydomain.com
SmtpMaxMessagesPerConnection : 20
SourceIPAddress : 0.0.0.0
SourceRoutingGroup : Exchange Routing Group (DWBGZMFD01QNBJR)
SourceTransportServers : {SERVER1}
TlsAuthLevel :
TlsDomain :
UseExternalDNSServersEnabled : False
Any help would be greatly appreciated as I am
stuck...
Luca

Hi Allen,
Thank you very much for your reply.
The Postfix TLS Manager is enabled in master.cf
tlsmgr unix - - n 1000? 1 tlsmgr
and running
server7:/etc/postfix # ps -efa|grep tls
postfix 11967 11863 0 11:21 ? 00:00:00
tlsmgr -l -t unix -u
Every other (Linux/UNIX) server has no problem e.g.:
Jan 5 11:28:36 server7 postfix/smtpd[12215]: connect from server2.mydomain.com[192.168.20.20]
Jan 5 11:28:36 server7 postfix/smtpd[12215]: Anonymous TLS connection established from server2.mydomain.com[192.168.20.20]: TLSv1 with cipher DHE-DSS-AES256-SHA (256/256 bits)
Jan 5 11:28:36 server7 postfix/smtpd[12215]: B5502946AB0: client=server2.mydomain.com[192.168.20.20]
Jan 5 11:28:36 server7 postfix/cleanup[12221]: B5502946AB0: message-id=<[email protected]>
Jan 5 11:28:36 server7 postfix/qmgr[12200]: B5502946AB0: from=<[email protected]>, size=1026, nrcpt=1 (queue active)
Jan 5 11:28:36 server7 postfix/smtpd[12215]: disconnect from server2.mydomain.com[192.168.20.20]
Jan 5 11:28:37 server7 postfix/smtpd[12225]: connect from localhost[127.0.0.1]
Jan 5 11:28:37 server7 postfix/smtpd[12225]: 4076A946AB1: client=localhost[127.0.0.1]
Jan 5 11:28:37 server7 postfix/cleanup[12221]: 4076A946AB1: message-id=<[email protected]>
Jan 5 11:28:37 server7 postfix/qmgr[12200]: 4076A946AB1: from=<[email protected]>, size=1778, nrcpt=1 (queue active)
Jan 5 11:28:37 server7 postfix/smtpd[12225]: disconnect from localhost[127.0.0.1]
Jan 5 11:28:37 server7 postfix/smtp[12222]: B5502946AB0: to=<[email protected]>, relay=127.0.0.1[127.0.0.1]:10024, delay=0.54, delays=0.05/0.01/0.01/0.47, dsn=2.0.0, status=sent
(250 2.0.0 from MTA(smtp:[127.0.0.1]:10025): 250 2.0.0 Ok: queued as 4076A946AB1)
Jan 5 11:28:37 server7 postfix/qmgr[12200]: B5502946AB0: removed
Jan 5 11:28:37 server7 postfix/cleanup[12221]: 4401F946AB0: message-id=<[email protected]>
Jan 5 11:28:37 server7 postfix/qmgr[12200]: 4401F946AB0: from=<[email protected]>, size=1920, nrcpt=1 (queue active)
Jan 5 11:28:37 server7 postfix/local[12226]: 4076A946AB1: to=<[email protected]>, relay=local, delay=0.02, delays=0/0.01/0/0, dsn=2.0.0, status=sent (forwarded as 4401F946AB0)
Jan 5 11:28:37 server7 postfix/qmgr[12200]: 4076A946AB1: removed
Jan 5 11:28:37 server7 postfix/smtp[12227]: Untrusted TLS connection established to 192.168.20.10[192.168.20.10]:25: TLSv1 with cipher AES128-SHA (128/128 bits)
Jan 5 11:28:37 server7 postfix/smtp[12227]: 4401F946AB0: to=<[email protected]>, orig_to=<[email protected]>, relay=192.168.20.10[192.168.20.10]:25,
delay=0.29, delays=0/0.01/0.02/0.25, dsn=2.6.0, status=sent (250 2.6.0 <[email protected]> [InternalId=619] Queued
mail for delivery)
Jan 5 11:28:37 server7 postfix/qmgr[12200]: 4401F946AB0: removed
and if you take a look at the lines in bold you will see that mails can be delivered over TLS to that very Exchange server (the mailboxes are on that server)...
To summarise:
exchange --> postfix with TLS = session disconnected (and everything seems to be initiated by the exchange server -if I read the logs correctly)
postfix --> exchange with TLS = works
any further hints?
Thank you very much in advance,
Luca

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