Exchange 2007 to 2013 mail flow issue

I had this question after viewing Exchange 2007 to exchange 2013 mail flow not working during migration.


I am facing the same issue.

There is no firewall between the old and new servers, windows firewalls are disabled in both.  Exchange2007 can do the telnet port 25 to Exchange2013 successfully but Exchange2013 unable to telnet with port25 with 2007.
Faseen AhmedAsked:
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Vidit BhardwajAdminCommented:
Are you able to telnet to local Host on the 2007 server ??
Faseen AhmedAuthor Commented:
Yes I am able to do..
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Faseen AhmedAuthor Commented:
We tried before creating connectors but didn't make any difference.
Vidit BhardwajAdminCommented:
Ok so localhost works, now check on 2007 server if the IP address of 2013 server added to any of the receive connector apart from default receive connector?
Vidit BhardwajAdminCommented:
Or if it falls in any range or subnet in any other receive connector ..also do other 2007 server able to reach to this server using telnet ?
MASEE Solution Guide - Technical Dept HeadCommented:
Hi Faseen,
You need only "Exchange server Authentication" Ticked for inter server mail flow. Make sure port 25 and port 2525 (Exchange2013 only)  is not blocked.
Exchnage 2007
Exchange 2007Exchange 2013
Exchange 2013
Thanks
MAS
Vidit BhardwajAdminCommented:
Make sure you haven't added the IP address of Exchange 2013 servers on 2007 receive connector and it's just falling in default IP range from 0.0.0.0-255.255.255.255 which should be default connector on 2007 with exchange server permission group enabled
Faseen AhmedAuthor Commented:
Verified,

Do we need to disable the additional receive and send connectors we created for this communication?
MASEE Solution Guide - Technical Dept HeadCommented:
-->Do we need to disable the additional receive and send connectors we created for this communication?
No need.
Faseen AhmedAuthor Commented:
Default 2007New connectro for 2013 on server 2007
MASEE Solution Guide - Technical Dept HeadCommented:
What is the purpose of the second receive connector(Exch2013) ?
Why do you need it to listen 587 and 465? Ths will create conflict in server.
Vidit BhardwajAdminCommented:
You need not to have any other specific connector for 2013 server just disable that and let the default connector receive the request
Faseen AhmedAuthor Commented:
I have disabled the connector for 2013 but still its not.
MASEE Solution Guide - Technical Dept HeadCommented:
Please check after restarting Transport service. Run this command from Powershell.
Restart-Service MSExchangeTransport

Open in new window

Faseen AhmedAuthor Commented:
I have tried in both servers but didn't work.
Vidit BhardwajAdminCommented:
Than please make sure if you have any other connector apart from default receive connector which has this IP address remove that IP from that receive connector on exchange server.

Also it can be related to TLS version enabled in 2007 and 2013 server they should have all the TLS version enabled
Faseen AhmedAuthor Commented:
We have connectors for scanner machines and exchange POP3 application (Which is downloading the emails from yahoo and forwarding to our Exchange server 2007).

Exchange server IP is 172.20.1.36.

See the other receive connectors
Capture1.PNG
Capture.PNG
Pete LongTechnical ConsultantCommented:
Anti Virus Software? (McAfee Loves to Break Exchange Mail Flow)
MASEE Solution Guide - Technical Dept HeadCommented:
Agree with Pete Long. Please check after turning off the firewall and anti-virus.
Faseen AhmedAuthor Commented:
There was AVG and we stopped it completely and no result.
MASEE Solution Guide - Technical Dept HeadCommented:
Can you send an email from Exchange 2007 to 2013 and back to 2007?
Check the queue viewer in both servers and post the error if any.
Faseen AhmedAuthor Commented:
Yes I can send from 2007 to 2013. But cannot reply it.

Email are getting queued and no error.
MASEE Solution Guide - Technical Dept HeadCommented:
Please post a screenshot
Faseen AhmedAuthor Commented:
AACC.png
Vidit BhardwajAdminCommented:
So basically no error here, can you enable intra org connector logging on 2013.

Set-transportserver -Identity servername -IntraOrgConnectorProtocolLoggingLevel verbose

Than check in the smtp send logs for hub and see what you see there.
Faseen AhmedAuthor Commented:
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,23,172.20.1.120:33517,172.20.1.120:475,<,250-SIZE 36700160,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,24,172.20.1.120:33517,172.20.1.120:475,<,250-PIPELINING,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,25,172.20.1.120:33517,172.20.1.120:475,<,250-DSN,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,26,172.20.1.120:33517,172.20.1.120:475,<,250-ENHANCEDSTATUSCODES,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,27,172.20.1.120:33517,172.20.1.120:475,<,250-AUTH,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,28,172.20.1.120:33517,172.20.1.120:475,<,250-X-EXPS EXCHANGEAUTH GSSAPI NTLM,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,29,172.20.1.120:33517,172.20.1.120:475,<,250-X-EXCHANGEAUTH SHA256,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,30,172.20.1.120:33517,172.20.1.120:475,<,250-8BITMIME,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,31,172.20.1.120:33517,172.20.1.120:475,<,250-BINARYMIME,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,32,172.20.1.120:33517,172.20.1.120:475,<,250-CHUNKING,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,33,172.20.1.120:33517,172.20.1.120:475,<,250-XEXCH50,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,34,172.20.1.120:33517,172.20.1.120:475,<,250-XRDST,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,35,172.20.1.120:33517,172.20.1.120:475,<,250-XPROXY,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,36,172.20.1.120:33517,172.20.1.120:475,<,250-X-MESSAGECONTEXT ADRC-2.1.0.0 EPROP-1.2.0.0,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,37,172.20.1.120:33517,172.20.1.120:475,<,250-XSESSIONPARAMS MDBGUID,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,38,172.20.1.120:33517,172.20.1.120:475,<,250-XSYSPROBE,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,39,172.20.1.120:33517,172.20.1.120:475,<,250 XMSGID,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,40,172.20.1.120:33517,172.20.1.120:475,>,X-EXPS EXCHANGEAUTH SHA256 ,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,41,172.20.1.120:33517,172.20.1.120:475,>,<Binary Data>,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,42,172.20.1.120:33517,172.20.1.120:475,<,235 <authentication information>,
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,43,172.20.1.120:33517,172.20.1.120:475,*,SMTPSendEXCH50 SendRoutingHeaders SendForestHeaders SendOrganizationHeaders SMTPSendXShadow,Set Session Permissions
2018-05-10T12:02:58.227Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,44,172.20.1.120:33517,172.20.1.120:475,>,XSESSIONPARAMS MDBGUID=52c163ad642d4508994d133e348c79b0,
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,45,172.20.1.120:33517,172.20.1.120:475,<,250 2.0.0 XSESSIONPARAMS OK,
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,46,172.20.1.120:33517,172.20.1.120:475,*,,sending message with RecordId 622770257925 and InternetMessageId <4790AE11E0156748AF6AF7826C1F2B8405CDA77E@MYKULWS2355.kul-dc.dhl.com>
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,47,172.20.1.120:33517,172.20.1.120:475,>,"MAIL FROM:<Aamir.Khan@dhl.com> SIZE=268336 AUTH=<> XMESSAGECONTEXT=ADRC-2.1.0.0,EPROP-1.2.0.0 XMSGID=<4790AE11E0156748AF6AF7826C1F2B8405CDA77E@MYKULWS2355.kul-dc.dhl.com>",
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,48,172.20.1.120:33517,172.20.1.120:475,>,RCPT TO:<thamer.alshgair@aacc-ltd.com>,
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,49,172.20.1.120:33517,172.20.1.120:475,<,250 2.1.0 Sender OK,
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,50,172.20.1.120:33517,172.20.1.120:475,<,250 2.1.5 Recipient OK,
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,51,172.20.1.120:33517,172.20.1.120:475,*,,Transfering 1 resolved and 3 unresolved recipient(s)
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,52,172.20.1.120:33517,172.20.1.120:475,>,BDAT 6070,
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,53,172.20.1.120:33517,172.20.1.120:475,*,,Sending blob ADRC-2.1.0.0
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,54,172.20.1.120:33517,172.20.1.120:475,<,"250 2.6.0 CHUNK received OK, 6070 octets",
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,55,172.20.1.120:33517,172.20.1.120:475,*,,Transfering 11 mailitemlevel and 18 recipient level properties for recipient(s) thamer.alshgair@aacc-ltd.com
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,56,172.20.1.120:33517,172.20.1.120:475,>,BDAT 911,
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,57,172.20.1.120:33517,172.20.1.120:475,*,,Sending blob EPROP-1.2.0.0
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,58,172.20.1.120:33517,172.20.1.120:475,<,"250 2.6.0 CHUNK received OK, 911 octets",
2018-05-10T12:02:58.242Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,59,172.20.1.120:33517,172.20.1.120:475,>,BDAT 268336 LAST,
2018-05-10T12:02:58.414Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,60,172.20.1.120:33517,172.20.1.120:475,<,250 2.0.0 OK,
2018-05-10T12:02:58.414Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,61,172.20.1.120:33517,172.20.1.120:475,>,QUIT,
2018-05-10T12:02:58.414Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,62,172.20.1.120:33517,172.20.1.120:475,<,221 2.0.0 Service closing transmission channel,
2018-05-10T12:02:58.414Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7D,63,172.20.1.120:33517,172.20.1.120:475,-,,Local
2018-05-10T12:03:31.933Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7E,0,,172.20.1.36:25,*,,attempting to connect
2018-05-10T12:03:31.933Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7E,1,172.20.1.120:33567,172.20.1.36:25,+,,
2018-05-10T12:03:31.933Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7E,2,172.20.1.120:33567,172.20.1.36:25,-,,Remote
Vidit BhardwajAdminCommented:
So we are closing the session as soon as we open it:
2018-05-10T12:03:31.933Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7E,1,172.20.1.120:33567,172.20.1.36:25,+,,
2018-05-10T12:03:31.933Z,Intra-Organization SMTP Send Connector,08D5B66C15947A7E,2,172.20.1.120:33567,172.20.1.36:25,-,,Remote

I assume 172.20.1.36 is your 2K7 IP address, there is definitely some issue in communication this needs active troubleshooting I think, I would suggest enable the receive connector logs on the 2K7 as well to have the whole communication, look for the random port we open from 2K13 in this case it was 33567 similar you will find that in receive connector logs so you know if we are reaching the 2K7 and if we are getting any error there.

Also do Telnet to 2k7 once more what are verbs you see after giving EHLO commands?
Faseen AhmedAuthor Commented:
About telnet.

Telnet from 2013 to 2007 with port 587 works for SMTP. And can send email.

But if we do for port 25 its connects and rejects immediately.
Vidit BhardwajAdminCommented:
Port 25 is the one we should worry about, if telnet is also not working we need to check with network team

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MASEE Solution Guide - Technical Dept HeadCommented:
Faseen AhmedAuthor Commented:
We skipped this part and moved all users in single short.
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