Apple Mac EMail Help!

MuttsNutts · 24 Jul 2012 at 09:58

Right chaps a tricky sticky one me thinks can anyone help?

I'w working on a customers site then runs Exchange 2003, the MD has a MAC at home that wants his Business email setup on it.

He brought it into the office and I set it up no problem tested all ok on the internal network incoming on IMAP and outgoing to SMTP also tested it on a wireless 3G dongle so it worked external too.

He took it home and reports he can recieve email ok but not send it.....?
so i go to his house to check, all settings are perfect and it just sits there, I diagnose further by RDP to the exchange server and checking it's connections to the SMTP server and when the MAC tries to connect it comes up with the connection in exchange SMTP as a connection it even has the username of the MD so i know it the MAC that's connected in so that rules out firewalls etc as it does connect you see but one thing i have noticed is the public IP thats displayed in the SMTP server is different from the public IP address of the MAC's internet connection i found this IP to belong to BT some sort of relay or somthing and yes the MD's ISP is BT, I even trusted this IP address in exchange to all relay but still will not send.

on the MAC using connection doctor I find in it's logs it does connect and send the EHLO or HELLO commands yet email wil still not relay.

So its somthing to do with the BT network can anyone
Help..... im going nuts here

BTW it works fine on all iPhone on the 3G connection and all other users home broadband wireless etc not tried iPhone on the MD's home broadband though

esK` · 24 Jul 2012 at 11:02

You could try setting the SMTP to mail.btinternet.com and put it through bt's servers, I've used this before and it works.

tribz · 24 Jul 2012 at 11:24

Domain name? BT used to need the domain name registering with their safe list for sending. Maybe his home connection will only allow sending via his btinternet.com/btconnect.com email address and not the domain name.

Or ..

His home connection only allows connections to his own ISP's SMTP server.

Edit, could he not spring for Office 2011 so that he can use Outlook?

MuttsNutts · 24 Jul 2012 at 13:22

You could try setting the SMTP to mail.btinternet.com and put it through bt's servers, I've used this before and it works.

I used smtp.btconnect.com and some emails did send ok via this but it's basic text authentication so not secure as i said this is the MD and would like his emails to be safe from mail capture from open traffic

could he not spring for Office 2011 so that he can use Outlook?

He have Office 2011 for the MAC but the bloody wally only bought the home & student version which does not include Outlook it's does as a trial so i have setup the account in there and again it wont send or connect i get Error Code 17997 when trying to send email Outlook wont even download the emails.

thanks for the input guys - im even thinking of downloading Thunderbird to see if that works any better?

MuttsNutts · 24 Jul 2012 at 13:37

When i setup outlook as stated above I used the Exchange email account setup this didnt work however I have just setup as a internet email account and entered the mailserver external address for IMAP "mailserver.domain.co.uk using SSL for send and receive it says it can connect it's currently downloading all 5 billion emails ok not that many but a few thousend anyhow....

Ive whacked an email in and sent it it's sat in outbox now waiting for the sync to complete, fingers crossed?

if it works will tell him to buy outlook/upgrade his office version or may try Thunderbird.
I think this is how the iPhones are setup and they work ok......

MuttsNutts · 24 Jul 2012 at 16:55

MuttsNutts said:
When i setup outlook as stated above I used the Exchange email account setup this didnt work however I have just setup as a internet email account and entered the mailserver external address for IMAP "mailserver.domain.co.uk using SSL for send and receive it says it can connect it's currently downloading all 5 billion emails ok not that many but a few thousend anyhow....

Ive whacked an email in and sent it it's sat in outbox now waiting for the sync to complete, fingers crossed?

if it works will tell him to buy outlook/upgrade his office version or may try Thunderbird.
I think this is how the iPhones are setup and they work ok......

I know I know Quoting myself LOL

All worked a treat via Outlook as setup above, got the MD to fork out another £129.99 for the Office Upgrade lol the dude is happy as larry now.
Kinda fixed myself but some input from you guys did help so thanks.....

if only they had gone ahead with the server replacment so they would be on Exchange 2010 by now then this would not be an issue..... you watch a month or two down the line they will buy the new server ha ha ha

tribz · 24 Jul 2012 at 20:51

Nice one, good job. It’s things like this you do for the MD that can quite often help with the future purchasing decisions so yes, it could be time for a new server soon.