Office 365 & installing an SSL certificate in SBS2003

Hi All,

I'm after a bit of guidance.

A client is transitioning from SBS2003-based MS Exchange to the cloud-based MS Office 365. However, things are not going quite to plan. This is my first experience with this process and I've hit a snag.

I'm using the staged migration method and already realised that I'm committed to this path now that I've started it. So, I need to complete this method before Office 365 will be happy.

I've created a temporary Windows 2008 server in order to run the MS migration software. I've also managed to get AD to synchronise. However, to sync the mailboxes, it now appears that we must have a proper SSL ceertificate rather than the self-signed one we've always used before.

We've never bothered with commercial certificates as we've always managed to get by using self-signed ones so I'm not very familiar with this process and would appreciate a little guidance please.

Also, I have a concern that installing a proper certificate will prevent devices connecting that have the self-signed certificate installed. Is this the case? or will they work simply because there is now a trusted certificate available?
LVL 1
edz_pgtAsked:
Who is Participating?
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.

James HodgeManaging DirectorCommented:
Hello and welcome to office 365!

You will need an SSL Certificate to make this work (it can be done with a SSC but it gets so messy I wouldn't want to). The SSL Certificate is really for Outlook Anywhere and Autodiscover to work properly.

If you have never used an SSL Certificate before, there is no need to worry. They are so easy to setup and the provider will walk you through the process.

My first SSL Certs were from GoDaddy because that's where my DNS was. GoDaddy made it particularly simply so if you are unsure where to get one:
http://uk.godaddy.com/ssl/ssl-certificates.aspx

Installing an SSL Certificate will not effect your existing certificates.

Good Luck

James
0

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
Simon Butler (Sembee)ConsultantCommented:
As long as you use the same host name on the trusted SSL certificate as you have on the self signed certificate then everything will continue to work correctly. The probelms will come if you use a different host name.

Simon.
0
edz_pgtAuthor Commented:
Thanks guys.

Simon > If for any reason I get the hostname wrong on the new certificate, will it cause the old certificate and people's configs to stop working? or will it simply mean my new config doesn't work?
0
Big Business Goals? Which KPIs Will Help You

The most successful MSPs rely on metrics – known as key performance indicators (KPIs) – for making informed decisions that help their businesses thrive, rather than just survive. This eBook provides an overview of the most important KPIs used by top MSPs.

Simon Butler (Sembee)ConsultantCommented:
You cannot have multiple certificates active at the same time.
Therefore if you use a different name then anything accessing web services (ActiveSync, RPC over HTTPS etc) will stop working because the trust isn't there.

Simon.
0
edz_pgtAuthor Commented:
I'd better get this right then! :)

Thanks again. I'm just researching the process of installing an SSL cert on a 2003 machine. It seems that the GoDaddy tutorials don't go back that far!
0
edz_pgtAuthor Commented:
0
James HodgeManaging DirectorCommented:
Yes, that will do the job.

Look at your existing Self-Signed Certificate to confirm host name to ensure that you match it when creating the new request.

James
0
edz_pgtAuthor Commented:
Thanks.
0
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
Exchange

From novice to tech pro — start learning today.