I'm having a few issues doing a cutover migration from our internal on-premises Microsoft Exchange to a hosted Exchange on Office365.

I'm trying to do the "Prepare for Migration" step covered here:https://support.office.com/en-ca/article/Perform-a-cutover-migration-of-email-to-Office-365-9496e93c-1e59-41a8-9bb3-6e8df0cd81b4#CreateEndpoint I'm trying to install Outlook Anywhere and have Office365 be able to access our emails.

The problem that I'm having is related to the certificates installed. Our internal on-premises Exchange FQDN is of machine.company.local, not machine.company.com, and it's using the self-signed certificate that it generated.

Steps I've attempted:

1. Install a .com version of our third party certificate. This creates the 12014 errors:

MSExchangeTransport 12014 - " Microsoft Exchange could not find a certificate that contains the domain name machine.company.local in the personal store on the local computer. Therefore, it is unable to support the STARTTLS SMTP verb for the connector Default TOINTERNET with a FQDN parameter of machine.company.local. If the connector's FQDN is not specified, the computer's FQDN is used. Verify the connector configuration and the installed certificates to make sure that there is a certificate with a domain name for that FQDN. If this certificate exists, run Enable-ExchangeCertificate -Services SMTP to make sure that the Microsoft Exchange Transport service has access to the certificate key.

Additionally, Office365 can't connect to our internal exchange server.

How would I go about this?

On another note, will Microsoft be okay with a third-party signed .local certificate?

• Edited by cKevi Friday, March 27, 2015 5:58 PM
• Moved by Jason Johnston [MSFT]Microsoft employee Friday, March 27, 2015 6:16 PM Not a development question.

Hi,

For exchange cutover migration, you need a public SSL certificate and a internet routeable domain. After getting up public SSL, did you assign any service to the certificate? Make sure that your autodiscover is working fine as O365 tries to connect your Exchange using autodiscover. You can test your outlook anywhere and autodiscover settings from testconnectivity.microsoft.com and yes Microsoft don't have any issue with .local entry in 3rd party certificate. Hope this answers your question. Thanks.