Ssl – Exchange 2007 New SSL Certificate Breaks Iphone access

1. Yes you can continue to use your 03 box as a mail server. You can also have it as your "SMTP Gateway/Transport" still if it is where all your email comes into from the internet.

2. OWA will be tricky since you can only have it pointing to a single server. So existing mailboxes on the 2003 box won't be able to use OWA until they are migrated (unless you go through a big ordeal that I don't want to describe here).

3. You will need a certificate for Outlook Anywhere. Regardless, you'll need to setup autodiscover.domain.com DNS records externally for Outlook Anywhere to work properly automagically.

Things to note from our migration:

-Blackberry stuff can be tricky, move the BESAdmin account first. -Activesync relies on the Client Access stuff, so either move them all first, or all last. This will affect OWA though since the same rules apply. -if you have a small enough company (under 500 people) I would strongly recommend moving around 25-50 on a weekend, let them test throughout the next 2 weeks, then move EVERYONE else in a single weekend. -you shouldn't have to mess with their outlook profiles -Migrate resource mailboxes over and then convert them to true "resource mailboxes" using Powershell and OWA

The things that I remember vividly is that OWA/Activesync definitely broke if you moved it over to the 07 box first. So we ended up moving all of the OWA/Activesync users at the same time and then moving the firewall rules to redirect to the 07 box.

EDIT: I'm referring to what happens to OWA if you only have a single Exchange 07 server and don't bother to setup 2 different URLs and redirects for OWA clients. See the technet article I refer to in the comments below.

This is the correct syntax to use in the Exchange Management Shell for Exchange 2007 running on Server 2008. This command assumes that your Windows domain and web domain are not the same. If they are the same, you don't need to list as many Subject Alternative Names.

New-ExchangeCertificate -GenerateRequest -Path c:\cert.csr -KeySize 2048 -SubjectName "c=Whois Country, s=Whois State, l=Whois City, o=Whois Organization Name, cn=mail.externaldomain.com" -DomainName exchangeServerName, exchangeServerName.internalDomain.local, autodiscover.externalDomain.com, autodiscover.internalDomain.local -PrivateKeyExportable $True