Calling all SMTP Gurus!
Any SMTP gurus out there?
I’ve got a very odd conundrum -
I use Vodafone for my GSM provider - who allow you access your phone’s MailBox via Mail (i.e. you get a mail account into which your voicemail goes, and you can SMS via outbound email - at 10p a go.)
The odd thing is that I cannot send out via their SMTP Server - or rather I cannot authenticate to it via my Mail client.

Mac OS X Mail.app and Entourage 2004 refuse to allow the Authentication Protocol that the server uses (AUTH LOGIN).

But strangely, Entourage X (the old version) can authenticate to it (and I can authenticate by hand via telnet.)
Here is a transcript:
Widebook:~ diggory$ telnet smtp.vodafone.net smtp
Trying 212.183.156.228…
Connected to www.vodafone.net.
Escape character is ‘^]’.
220 Smtp Filter ESMTP Server ready
EHLO Localhost
250-Smtp Filter Hello
250 AUTH=LOGIN
AUTH LOGIN
334 VXNlcm5hbWU6
RGlnZ29yeQ==
334 UGFzc3dvcmQ6
(Encoded Password Removed)
235 Authentication successfull
Does anyone out there have any idea why the Client apps are throwing a fit over this?
Jim Frisk says:
Not sure about your specific problem but a few comments:
1. Using the SMTP servers provided by your Internet access provider does not normally require authentication - so try without.
2. Try another Authenticated SMTP service like http://www.authsmtp.com - I find this very useful as I use the same computer with multiple ISP’s!
July 10th, 2004 at 5:57 pm
Diggory Laycock says:
Thanks Jim - AuthSMTP looks like an interesting work-around for the travelling salesman problem - but I’m not prepared to pay to send my email.
I did some more research and I believe that Mail.app and the new Entourage are more strict about smtp - I think they only send unauthenticated on port 25 - and authenticated on 587. (To help reduce unauthenticated spam relaying)
I believe that vodafone’s SMTP server does not accept on 587.
(but I could be wrong on both of these…)
July 16th, 2004 at 2:28 pm
Bryan says:
I have the same problem with Entourage. I can connect by hand as well from a telenet session to port 25, and 587. I know this is a problem with Entourage because unlike you if I configure the mail client in OS X, I can send mail using it. Any help?
November 7th, 2004 at 10:06 am
Jim Frisk says:
Take your point about paying but for about $2 a month I don’t have the time to spend looking for a freebie
July 26th, 2005 at 12:40 pm
Listening Post » Blog Archive » Weblogs lead me to two purchases says:
[...] The first is the weblog MonkeyFood with this post, titled Calling All SMTP Gurus leading me to purchase an outbound email management service from AuthSmtp. After working out of yet another coffee shop on a free wifi connection where I was not able to send my email from any email client - Entourage or Apple Mail on Mac OSX, or Outlook on Windows XP, I started doing some Google searching on the problem. One of several search results on the first 2 pages of each my Google searches was the post above from the MonkeyFood blog. Upon reading the post, I noticed one of the comments provided by a reader of MonkeyFood mentioned the AuthSmtp service. Once I discovered that the root of my outbound email problems was the fact that the Internet Service Providers (ISPs) for these coffee shops blocked connections to the SMTP port (Port 25) unless your were sending email from inside their network (i.e. you were the subscriber and not the coffee shop), I knew I had a problem. [...]
August 16th, 2006 at 5:18 pm
Sheila says:
Not an ideal (secure) solution, but… according to the Vodafone.net website help….. NOTE: If your client does not support SMTP authentication, please set your SMTP server to be send.vodafone.net
Hope this helps get those emails out!
September 18th, 2006 at 6:57 pm
anonymous email says:
Coming home from a one month holidy, my provider (BigGlobe NEC) switch off port 25.
In my case the 587 switch on the SMTP port did the trick.
October 7th, 2006 at 7:41 am
David Jackson says:
I also use Authsmtp.com and have done for over a year now - tried various services but it was the only one that was flexible enough and actually worked as I need.
Would thouroughly recommnend it and never had any problems sending mail since.
November 27th, 2006 at 5:09 pm
Ian says:
Hi, I have a problem too with vodafone and mail sending - I tried setting up the outgoing as send.vodafone.net - but the software seems to ignore the send and comes up with a message saying it cannot send using the smtp - I spent half a day at the mac shop and at Vodafone trying to solve this and neither seemed to know what was going on…
April 26th, 2008 at 6:34 pm