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Can't send email from Andriod on Exchange 2003

I have a customer on SBS 2003 using exchange. As far as I know up until now it worked to send and receive email on his Andriod (I was told). Yesterday I replaced their old cisco router with Untangle firewall.

Now the one user says that he can receive emails to his Andriod but when he tries to send emails it just stays in his outbox and does not send. It is Sunday so I don't knwo about the other users

He can still send and receive from his outlook client which is also working for other users.

I opened port 25 to the exchange server.

Did I miss something...do I need to open another port?

Any other ideas what to look for?

Alan Hardisty

Make sure you also open port 443 for Activesync.

Craig Beck

Look in the Untangle logs to see what protocol/port the phone is using when it tries to send.

I'm not sure about what Alan said, as it sounds like you can receive mail which should also use ActiveSync.

Gerhardpet

ASKER

I looked in the old cisco router and the only 2 ports forwarded are 25 and 443

Alan Hardisty

How is the account on the Android configured?

Exchange or SMTP/POP3?

Gerhardpet

ASKER

It is configured as Exchange

Gerhardpet

ASKER

I did not configure the phones as I just started working with this customer. I just called the user and he does not even know if his calendar is syncing which makes me think that they are all on POP3. Since they had exchange I assumed that active sync was being used.

Gerhardpet

ASKER

I notice that they is no SSL certificate installed other then the self generated one.

As far as I know activesync will not even work for Android (and other phones that use the activesync protocal) with out a valid SSL certificate from a certificate authority

this is what I get when I do a test on https://www.testexchangeconnectivity.com

      Testing the SSL certificate to make sure it's valid.
     The SSL certificate failed one or more certificate validation checks.

      Test Steps

      ExRCA is attempting to obtain the SSL certificate from remote server mail.domain.ca on port 443.
     ExRCA successfully obtained the remote SSL certificate.

      Additional Details
      Validating the certificate name.
     The certificate name was validated successfully.

      Additional Details
      Validating certificate trust for Windows Mobile devices.
     Certificate trust validation failed.

      Test Steps

      ExRCA is attempting to build certificate chains for certificate CN=mail.domain.ca, CN=companyweb, CN=eagle, CN=localhost, CN=eagle.domain.local.
     A certificate chain couldn't be constructed for the certificate.
      Tell me more about this issue and how to resolve it

      Additional Details
     The certificate chain didn't end in a trusted root. Root = CN=mail.domain.ca, CN=companyweb, CN=eagle, CN=localhost, CN=eagle.domain.local

Alan Hardisty

Please re-run the test but specify manual server settings and tick the Ignore Trust for SSL check box and see if it passes.

As long as the name on the SSL certificate matches the FQDN you specify for Activesync e.g., mail.domain.com, then it should be fine with ANY mobile device.

Gerhardpet

ASKER

Please re-run the test but specify manual server settings and tick the Ignore Trust for SSL check box and see if it passes.

Yes the connectivity test is successful when I Ignore Trust for SSL

How could I find out if SBS 2003 is configured as POP3/SMTP?

Alan Hardisty

Good news that it passes. Should mean that the Android can use an Exchange account happily, but if configured for SMTP/POP3, then it won't be able to send as your server won't let it relay.

If you have port 110 open on your firewall and the Microsoft Exchange POP3 Service started and running, then POP3 should work remotely.

Gerhardpet

ASKER

If you have port 110 open on your firewall and the Microsoft Exchange POP3 Service started and running, then POP3 should work remotely.

Ok meaning that if configured as POP3 then Android will need to use a different SMTP server for relay? Or can it use the SBS 2003 as a relay?

I have just opened port 110 on the firewall. From what I could tell port 110 was not open on the old cisco router but it was hard to figure out.

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Craig Beck

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Gerhardpet

ASKER

Ok the Android user is now able to send emails. He told me that he deleted a few emails that seemed to have halted all his email sending.

But now another user contacted me saying that he is not receiving any emails on his iPhone.

So far I have not done any work on the SBS 2003 box but it seems to me that my new customer is having connectivity issues

I have disabled port 110 forward

Alan Hardisty

Please run the same test on the test site for the problem user and report back the results if they don't pass.

Thanks

Alan

Gerhardpet

ASKER

Yes the does pass. All I had to do is delete the exchange account on the iPhone and recreate it which solved the problem.

Alan Hardisty

Thought it would be something like that.

Good news.

Are we all working now then?

Gerhardpet

ASKER

Yes now everything seems to be working. I have a mix of about 50 cell phones, BB's, iPhones and Androids

It is a new customer so I'm still trying to wrap my head around everything. Previous IT left a mess behind

Thanks for all the help

Alan Hardisty

Ah - nice mess to find yourself in.

If you get stuck with anything else - please feel free to ask a new question and drop a link here to it and I'll see if I can help.

Alan

Gerhardpet

ASKER

Thanks Alan

Alan Hardisty

You are welcome.