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edz_pgtFlag for United Kingdom of Great Britain and Northern Ireland asked on

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?
ExchangeSBSMicrosoft 365

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edz_pgt

8/22/2022 - Mon
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James Hodge

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Simon Butler (Sembee)

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ASKER
edz_pgt

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?
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edz_pgt

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!
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edz_pgt

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edz_pgt

Thanks.