As Michael and Andrew said, it's unsupported. Did you do a "netsh trace" to see what's happening, and/or do you have some other means of recording/monitoring (span/mirror port monitored by a machine running wireshark, perhaps) the smtp conversation?
If you didn't, I'd seriously consider reverting and running that test. Is the appliance on the same subnet as Exchange? Will Exchange deliver direct using IPv4 - that is, not using the appliance as a smarthost? Kurt On Fri, Feb 3, 2017 at 6:29 AM, Kelsey, John <[email protected]> wrote: > Setting the smart host property to use the IP address instead of the > hostname didn’t help. > > > > Disabling the IP Helper service on the Exchange server appears to have fixed > it. However…I’m not sure what the consequences of that will be or if that > is advised? > > > > From: [email protected] [mailto:[email protected]] > On Behalf Of Michael B. Smith > Sent: Friday, February 03, 2017 9:21 AM > To: [email protected] > Subject: RE: [NTSysADM] Exchange sending via IPv6 > > > > This is 2017 and it doesn’t speak IPv6? > > > > Yes, Exchange starting with 2013 will definitely prefer IPv6 over IPv4. > > > > From: [email protected] [mailto:[email protected]] > On Behalf Of Kelsey, John > Sent: Friday, February 3, 2017 8:15 AM > To: '[email protected]' > Subject: RE: [NTSysADM] Exchange sending via IPv6 > > > > Yes, the Sophos appliance is set as a smart host. I’m currently using the > FQDN of the appliance. I’ll try using its IPv4 address. > > > > Thanks! > > > > > > From: [email protected] [mailto:[email protected]] > On Behalf Of Kurt Buff > Sent: Thursday, February 02, 2017 11:57 PM > To: ntsysadm > Subject: Re: [NTSysADM] Exchange sending via IPv6 > > > > Are you using the Sophos appliance as a smarthost? Are you using the FQDN of > the appliance, or its IPv4 address? If the former, try the latter. > > I'd verify the vendor's claim, BTW - "netsh trace" is your friend: > https://msdn.microsoft.com/en-us/library/windows/desktop/dd569142(v=vs.85).aspx > > and > https://blogs.msdn.microsoft.com/canberrapfe/2012/03/30/capture-a-network-trace-without-installing-anything-capture-a-network-trace-of-a-reboot/ > > > > Kurt > > > > On Thu, Feb 2, 2017 at 8:13 PM, Kelsey, John <[email protected]> > wrote: > > Working on a new Exchange 2013 install. Outbound emails are failing and our > front-end email appliance vendor (Sophos) says its failing because Exchange > is sending the outbound emails using its ipv6 address instead of its ipv4 > address and the Sophos appliance doesn’t understand ipv6 ( I know, right?) > > > > I don’t see any obvious place to configure this in Exchange, and I know that > disabling ipv6 in Exchange is baaaaaad. > > > > So can I force Exchange to send only using its ipv4 address somehow? > > > > Thanks all. > > > > > > *************************************** > John C. Kelsey, MCSE, CCNA > Network Architect > Penn Highlands Healthcare > (: 814.375.3073 > 2 : 814.375.4005 > *: [email protected] > *************************************** > > > > > > This email and any attached files are sensitive in nature and intended > solely for the intended recipient(s). If you are not the named recipient you > should not read, distribute, copy or alter this email. Any views or opinions > expressed in this email are those of the author and do not represent those > of Penn Highlands Healthcare or its affiliates.. Warning: Although > precautions have been taken to make sure no viruses are present in this > email, the company cannot accept responsibility for any loss or damage that > arise from the use of this email or attachments. > > > > This email and any attached files are sensitive in nature and intended > solely for the intended recipient(s). If you are not the named recipient you > should not read, distribute, copy or alter this email. Any views or opinions > expressed in this email are those of the author and do not represent those > of Penn Highlands Healthcare or its affiliates.. Warning: Although > precautions have been taken to make sure no viruses are present in this > email, the company cannot accept responsibility for any loss or damage that > arise from the use of this email or attachments. > > This email and any attached files are sensitive in nature and intended > solely for the intended recipient(s). If you are not the named recipient you > should not read, distribute, copy or alter this email. Any views or opinions > expressed in this email are those of the author and do not represent those > of Penn Highlands Healthcare or its affiliates.. Warning: Although > precautions have been taken to make sure no viruses are present in this > email, the company cannot accept responsibility for any loss or damage that > arise from the use of this email or attachments.
