Exchange 2003 Outlook anywhere

i have an existing exchange 2003 sp2 on windows 2003 sp3. single server deployment.
all mailboxes are hosted on this server. no front end / back end configuration, just this one server.

i had OWA setup with an internal certificate. now i am attempting to migrate to the cloud on office 365 and it specifically states that outlook anywhere needs to be set up and that a public certificate needs to be used.

i previously had OWA working and RPC over HTTP with an internal certificate.

can someone provide me with detailed steps on setting up Outlook anywhere with my current configurations. i have already purchased a UC Certificate for up to 5 domains from GoDaddy and i am downloading Exchange 2007 w SP3 now for prep to install a CAS as per microsoft instructions.

however, my problem lies in the fact that every article i have come across just has high level steps and i am unsure of how to set this up.

please help.
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Simon Butler (Sembee)ConsultantCommented:
On Exchange 2003, if you have a certificate for then just do a regular certificate request for and replace the certificate in IIS manager. That is it, nothing else needs to be done because the host names stay the same.

Once you have response, run the same wizard again, pointing it at the response file.

You could probably get away with a free certificate from for that part.

Then use different host names for the Exchange 2007 SSL certificate.

netrescueAuthor Commented:
ok so Simon, thanks for the assist.
i am still a bit shaky here....
i do a cert req for (my public URL for OWA) - then what - do i submit this request to GoDaddy for creating the details for my public certificate?

then how do i set up Exchange 2007? can i install this on a Windows 2003 SP3 server?
i need the steps to get the whole thing working. those high level steps you provided are the same levels of feedback i am getting all over the internet and it seems like much more.

how do i get exchange 2003 to work with exchange 2007 as the front end?
i have to replace the old internal certificates with the new public certificates where? exchange 2003 IIS, Exchange 2007, firewall listener???

i need a lot more help on this item.
Simon Butler (Sembee)ConsultantCommented:
I hate to say this, but I think you need to get a consultant in.

The reason you are seeing just the high level steps is because this is pretty basic stuff, and most bloggers (myself included) will presume that there is a level of knowledge involved.
If you haven't used Exchange 2007 before then you are in for a huge learning curve because it is nothing like Exchange 2003 from a management point of view.
You can install Exchange 2007 on to Windows 2003, as long as it is Windows 2003 X64.

The questions you have asked would take me a good hour to research and write the answers to, and as I don't get paid to answer questions on this site, that isn't something I am prepared to do.

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netrescueAuthor Commented:
hey Simon,
again thanks for the help.
i know a lot about Exchange and finding my way around the network.
what i was trying to say is i need a high level list of steps that are a little more like this... just for an example:

1. do cert req on Exchange 2003 from IIS
2. use cert req file to get new cert created from public CA
3. import cert into rpc virtual directory on IIS on Exch 2003
4. install rpc/http component on exchange 2007 server
5. enable outlook anywhere on exchange 2007 and configure using wizard
6. import cert into rpc virtual directory on IIS on Exchange 2007 CAS server
7. import cert into OWA listener on firewall
8. any i missed?

thanks again for any assistance.
netrescueAuthor Commented:
i did the cert request on the exchange 2003 server from iis as described.
do i import it on the exchange 2003 server or on the exchange 2007 server?
when i attempt to import on Exchange 2007, i get an error stating the private key is missing (when i use the import-exchagnecertificate & enable-exchangecertificate command)
any ideas / help?
netrescueAuthor Commented:
ok all
although it seems like im updating myself here, i have made progress.
i have gotten this far. exchangeconnectivitytests reports the following as the only error.
what do i do to fix this?

The HTTP authentication test failed.
Tell me more about this issue and how to resolve it
Additional Details
Not all the required authentication methods were found. Methods Found: Basic Methods Required: NTLM
Iain MacMillanIT Regional Manager - UKCommented:
i would ignore the 2007/office 365 part just now, as Sembee said, its whole different ball game compared to 2003 (i'm shortly going from 2003 to 2013, and i have a consultant in as i've only ever used 5.5 and 2003).

To get the cert working first you need to replace the internal one on the 2003 box, via IIS, get the request done, and then when you have the cert, apply it as the security reply to import into the IIS / OWA site.  That should then allow you to update your firewall etc to operate your OWA service via HTTPS.

the domain you have setup -- like will then be what you point your mobile phones and Outlook clients to for external access / Outlook Anywhere.

Anywhere is setup via the Advanced account settings --> Exchange Proxy, i usually apply MSSTD:<name of your external email domain> so that the client only connects to this server (  Tick slow & fast networks, and if your having authentication issues, use basic to get things started for testing.

first time you connect Outlook internally, you will be prompted for login, please add your domain\username creds and password (tick the save pwd box if you wish or it will ask each time you launch).  that should be it working.  pretty much same process for adding exchange account to a mobile as well, same domain for SSL and use domain and user creds to create the link.

Now seek external help from the vendor you're buying Office 365 from.

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