Exchange 2007 migrating to cloud Office 365


I am going thru and starting a migration from on premises Exchange 2007 to Cloud based Office 365. I have done a check on the Microsoft Remote Connectivity Analyzer and it is coming back with an error of:

It says attempting to resolve host name was successful. Testing port 443 was successful.
Testing the SSL certificate to make sure it's valid.
  The SSL certificate failed one or more certificate validation checks.

When I use Outlook on my laptop outside my business network it connects up to my exchange and downloads and sends emails no problems.

I have a Go Daddy certificate installed on my server for the

Any ideas on where I can start with this?


Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Vasil Michev (MVP)Commented:
Which check specifically? Do you get certificate warnings or similar when accessing anything via OA externally?
Vincent BurtonCommented:
Some times this issue occurs because an intermediate certification authority (CA) certificate is not present on the device or on the Exchange Server server with which you are synchronizing.

You can visit this post to know about Purchasing and Installing Your SSL Certificate on Office 365:

Also have a look on this informative blog post: 

Hope it helps you!

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today

From novice to tech pro — start learning today.