Relay to Office365

Use this forum if you want to discuss a problem or ask a question related to a hMailServer beta release.
Post Reply
dmack
New user
New user
Posts: 4
Joined: 2014-05-20 18:29

Relay to Office365

Post by dmack » 2014-05-20 18:37

Just wondering if a new build is out that will work with Office365 & TLS?

Bill48105
Developer
Developer
Posts: 6192
Joined: 2010-04-24 23:16
Location: Michigan, USA

Re: Relay to Office365

Post by Bill48105 » 2014-05-20 20:05

dmack wrote:Just wondering if a new build is out that will work with Office365 & TLS?
No outgoing STARTTLS is not supported yet. Can you not do SSL on 465? That is pretty much universally supported if encryption is needed. If encryption is not needed then 587. I've not heard of anyone/anywhere that requires STARTTLS but have heard of places requiring some encryption.
hMailServer build LIVE on my servers: 5.4-B2014050402
#hmailserver on FreeNode IRC https://webchat.freenode.net/?channels=#hmailserver
*** ABSENT FROM hMail! Those in IRC know how to find me if urgent. ***

Bill48105
Developer
Developer
Posts: 6192
Joined: 2010-04-24 23:16
Location: Michigan, USA

Re: Relay to Office365

Post by Bill48105 » 2014-05-20 20:20

I was curious so I looked it up:
http://technet.microsoft.com/en-us/libr ... 54323.aspx

Based on that you have to use port 25 or 587. They say they don't support 465 with SSL which is beyond me. If they have SSL cert for STARTTLS they certainly should support the 465 SSL standard. Of course you won't get encryption if you do 25/587 but at least you should be able to send.

Can't say when outgoing STARTTLS will even be worked on as it depends on who gets time. I'd hound them to add support for 465 SSL though that should be trivial. Not such much for getting outgoing starttls in hmail.
Bill
hMailServer build LIVE on my servers: 5.4-B2014050402
#hmailserver on FreeNode IRC https://webchat.freenode.net/?channels=#hmailserver
*** ABSENT FROM hMail! Those in IRC know how to find me if urgent. ***

Bill48105
Developer
Developer
Posts: 6192
Joined: 2010-04-24 23:16
Location: Michigan, USA

Re: Relay to Office365

Post by Bill48105 » 2014-05-20 21:04

btw they say TLS but i take it they mean STARTLS since they state SSL On 465 is not supported. And SSL on 587 would not make sense
hMailServer build LIVE on my servers: 5.4-B2014050402
#hmailserver on FreeNode IRC https://webchat.freenode.net/?channels=#hmailserver
*** ABSENT FROM hMail! Those in IRC know how to find me if urgent. ***

dmack
New user
New user
Posts: 4
Joined: 2014-05-20 18:29

Re: Relay to Office365

Post by dmack » 2014-05-20 21:08

I believe you are right.

Bill48105
Developer
Developer
Posts: 6192
Joined: 2010-04-24 23:16
Location: Michigan, USA

Re: Relay to Office365

Post by Bill48105 » 2014-05-20 21:30

Did you try 587 with AUTH but no SSL?
hMailServer build LIVE on my servers: 5.4-B2014050402
#hmailserver on FreeNode IRC https://webchat.freenode.net/?channels=#hmailserver
*** ABSENT FROM hMail! Those in IRC know how to find me if urgent. ***

dmack
New user
New user
Posts: 4
Joined: 2014-05-20 18:29

Re: Relay to Office365

Post by dmack » 2014-05-20 21:42

Yes

Bill48105
Developer
Developer
Posts: 6192
Joined: 2010-04-24 23:16
Location: Michigan, USA

Re: Relay to Office365

Post by Bill48105 » 2014-05-20 23:31

No promises but if I get time I'll see if I can post a special build of hmail that partially supports outbound STARTTLS for SMTP using a specially configured Route. Been meaning to do that anyway as a 1st step but just been busy.
hMailServer build LIVE on my servers: 5.4-B2014050402
#hmailserver on FreeNode IRC https://webchat.freenode.net/?channels=#hmailserver
*** ABSENT FROM hMail! Those in IRC know how to find me if urgent. ***

dmack
New user
New user
Posts: 4
Joined: 2014-05-20 18:29

Re: Relay to Office365

Post by dmack » 2014-05-21 00:29

Okay, thanks!

Bill48105
Developer
Developer
Posts: 6192
Joined: 2010-04-24 23:16
Location: Michigan, USA

Re: Relay to Office365

Post by Bill48105 » 2014-05-22 15:48

I hacked up a special build to support smtp sending with STARTTLS for Routes and almost works but having handshake issues which I need to resolve. Most likely either a boost/openssl issue or a timing issue changing layers during the conversation

"unknown protocol" leads me to believe they can't negotiate but will need to mess with it later once the dust settles

Code: Select all

"SMTPC"	3568	2	"2014-05-21 22:48:33.097"	"192.168.3.3"	"RECEIVED: 250 AUTH LOGIN"
"DEBUG"	3568	"2014-05-21 22:48:33.097"	"TCPCconnection::GetSocket(): next_layer()"
"SMTPC"	3568	2	"2014-05-21 22:48:33.097"	"192.168.3.3"	"SENT: STARTTLS"
"DEBUG"	3568	"2014-05-21 22:48:33.097"	"TCPConnection::Write next_layer()"
"DEBUG"	3568	"2014-05-21 22:48:33.097"	"TCPConnection::STARTTLS_Handshake handshake1"
"DEBUG"	3568	"2014-05-21 22:48:33.097"	"TCPConnection::STARTTLS_Handshake handshake3"
"DEBUG"	3568	"2014-05-21 22:48:33.097"	"STARTTLS true"
"DEBUG"	3568	"2014-05-21 22:48:33.097"	"_stateSTARTTLS = 3"
"DEBUG"	3568	"2014-05-21 22:48:33.097"	"StartTLSState3() true"
"DEBUG"	3568	"2014-05-21 22:48:33.097"	"TCPCconnection::GetSocket(): lowest_layer()"
"SMTPC"	3568	2	"2014-05-21 22:48:33.097"	"192.168.3.3"	"SENT: EHLO WIN7-20"
"DEBUG"	2180	"2014-05-21 22:48:33.097"	"TCPConnection::Write ssl"
"DEBUG"	3568	"2014-05-21 22:48:33.128"	"TCPCconnection::GetSocket(): lowest_layer()"
"DEBUG"	2180	"2014-05-21 22:48:33.128"	"TCPCconnection::GetSocket(): lowest_layer()"
"TCPIP"	3568	"2014-05-21 22:48:33.128"	"TCPConnection - SSL handshake with client failed. Error code: 336031996, Message: unknown protocol, Remote IP: 192.168.3.3"
"DEBUG"	2180	"2014-05-21 22:48:33.128"	"The write operation failed. Remote IP: 192.168.3.3, Session: 2, Code: 336031996, Message: unknown protocol"
hMailServer build LIVE on my servers: 5.4-B2014050402
#hmailserver on FreeNode IRC https://webchat.freenode.net/?channels=#hmailserver
*** ABSENT FROM hMail! Those in IRC know how to find me if urgent. ***

Post Reply