Michael-I went ahead and created a receive connector on each Hub Transport 
server with the following settings:

Network Tab: Added vendor's IP to the 'Receive mail from remote servers...' area
Authentication Tab: Checked 'Externally Secured (for example, with IPsec)'
Permission Groups Tab: Checked 'Anonymous Users', 'Exchange Users', 'Exchange 
Servers'

I'm confused on the custom Send Connector piece. We setup an ADS account they 
will be authenticating to the Exchange server with, so wouldn't the outbound 
emails not require additional handling, since once it's submitted we're 
allowing them to send to any external domain?

Thanks,
Geoff

From: [email protected] [mailto:[email protected]] On 
Behalf Of Michael B. Smith
Sent: Wednesday, March 29, 2017 1:46 PM
To: [email protected]
Subject: [Exchange] RE: Removing Self-Issued Cert:

Yes, you just identified the issue yourself. You'll need both a custom receive 
connector and a custom send connector, but just for that subnet, not for all of 
your subnets.

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Orlebeck, Geoffrey
Sent: Wednesday, March 29, 2017 10:06 AM
To: '[email protected]'
Subject: [Exchange] RE: Removing Self-Issued Cert:

Joseph, thanks for the confirmation, I won't be removing the certificate 
anytime soon :)

Michael,
The vendor's error logging shows the self-signed certificate (issuer = EXSRVR1) 
is the one being presented and that's why it's failing-they don't trust the 
issuer (EXSRVR1).

Also, when you wrote the "last certificate set to use SMTP should be the one 
that is used", are you referring to when certs were assigned the services? Or 
are you saying I can specify the order we 'prefer' the certificates be used? I 
assumed the former, but wasn't sure.

One other thing is we have an IPsec VPN between the vendor and our organization 
to allow traffic to our CAS servers. Would Exchange be seeing this as internal 
traffic and attempting to respond with the internal certificate because the 
default Receive Connector encompasses the entire IPv4 address space 
(0.0.0.0-255.255.255.255)? I'm not sure if best practice is to go back and 
define all of our internal subnets to remove the "catch all" connector.

Thanks,
Geoff

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Joseph L. Casale
Sent: Tuesday, March 28, 2017 4:42 PM
To: '[email protected]' 
<[email protected]<mailto:[email protected]>>
Subject: [Exchange] RE: Removing Self-Issued Cert:


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click on links from unknown senders or unexpected emails.

To add a large point to that, the self-signed cert should *not* be removed or 
you'll break it. I don't know the intimate details however it's my 
understanding internal servers and consoles etc use this to communicate. I 
snaped a lab recently and removed it and after a reboot it was awefully 
broken...

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Michael B. Smith
Sent: Tuesday, March 28, 2017 5:28 PM
To: [email protected]<mailto:[email protected]>
Subject: [Exchange] RE: Removing Self-Issued Cert:

Use openssl to determine what cert is actually being presented. Or turn up 
logging on the relevant receive and send connectors and examine those logs for 
the third-party.

The LAST certificate set for use by SMTP should be the one that is used, except 
internally, which should use the internal default certificate.

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Orlebeck, Geoffrey
Sent: Tuesday, March 28, 2017 10:24 AM
To: '[email protected]'
Subject: [Exchange] Removing Self-Issued Cert:

We run Exchange 2010 in a two-node DAG. There is a third-party hosted product 
that we have an IPsec VPN with, but they fail to send email as they do not 
trust the certificate being presented to them. On each node, there is a 
self-signed certificate each server has issued to itself (EXSRVR1/EXSRVR2). We 
have an internal CA and third-party trusted cert set to SMTP services, is there 
any issue disabling/removing the SMTP service from the self-issued certificates?

Looking at this TechNet link 
https://technet.microsoft.com/en-us/library/dd351257(v=exchg.141).aspx<https://urldefense.proofpoint.com/v2/url?u=https-3A__technet.microsoft.com_en-2Dus_library_dd351257-28v-3Dexchg.141-29.aspx&d=CwMFAg&c=GtV7VYka8XzFJya76SH24R7OU_QKFTyBlklHoDMCjFY&r=WF1NZuUqAd1bRIxLFT_0wz8npqTRKjPr3_qzGO_dTx_Q3Taym2JWM42n-cKyG-6W&m=ROV4Ju70hyHc7_2pnt3WTtm9_sz0_gqp5l_NamklV4U&s=-eqt-XItvywwwoD0zgdifIKx6eQAcYgaBClJmdxdIvs&e=>)
 I can set the assigned services to 'None'. However, I'm curious if there will 
be any issues from internal Outlook clients using the Root CA certificate for 
SMTP (since it is trusted across all domain joined devices).

Here's a sanitized output of one of our CAS server's certificates:

[cid:[email protected]]

I appreciate any insight. Thank you.

-Geoff
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