SMTP and sending messages on the road

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It’s been a long-standing problem for laptop users – you have Outlook running nicely at home but when you travel it’s impossible to send messages.  Here’s what’s happening and how to avoid it.

The fix, that should work for most situations is to change the Outlook account settings to login for both receiving and sending messages.  It applies to POP and IMAP accounts only (not Exchange Server).  Go to the Account Settings and click on the ‘More Settings’ button.

In the Internet E-mail Settings go to the Outgoing Server tab.  Make sure that ‘My outgoing server (SMTP) requires authentication’ is selected.

For most situations ‘Use same settings as my incoming mail server’ is enough.  On rare occasions, your ISP or mail host has different SMTP login settings.

Click OK then use the ‘Test Account Settings’ button to make sure you can receive and send messages with the new settings.

This is where we have to add a big condition …. sending SMTP settings depend on what your ISP or mail host will allow.  We can only talk about the usual practice and common variations not how individual hosts are setup.  Any decent ISP or mail host should have instructions on their web site with the SMTP settings (server name, port and login requirements).  If not, contact their support desk.

Background

SMTP (Simple Mail Transport Protocol) is the way email is sent across the Internet.  Outlook sends your email out using SMTP to your mail host/ISP (for POP/IMAP accounts) then the mail host routes your message to its destination host, also via SMTP.

In the early days of the Internet, SMTP servers were open.  Anyone could use any SMTP server to send out email, which was handy when the servers and connections weren’t as reliable as they as these days.

Then spammers arrived and they made use of open SMTP to send their unwanted messages out.

So mail hosts (ISP’s, organizations) started to limit SMTP access to only authorized people/computers.  This was done in two ways:

  • Login with username and password. Most commonly with the same login as for receiving messages with POP or IMAP.
  • By IP address. Internet Service Providers (ISP) often used this method because it didn’t require any change by users.  SMTP access still didn’t require login but only computers using one of the ISP’s allocated IP addresses could send out messages.
    • That’s where roaming users had trouble. The portable computer could send messages when connected via the ISP’s connection (because it used an authorized IP address, allocated by the ISP) but not when away and using another ISP instead.

Unfortunately, ISP’s didn’t implement SMTP access very well or communicate the changes to either their customers or, sometimes, their own support staff.  There was, and still is, confusion all round.   As a global traveler, Office Watch’s Peter Deegan knows about sending email hassles better than most and has too many horror stories to tell.

Some ISP’s added IP blocking but made no provision for roaming users.  Others added both IP and login requirements but could not mix the two (i.e valid logins would not work because it came from a valid IP address!).

On top of all that, there are SMTP troubles on the road.  An overzealous mindset from some hotel and public Internet connections had the administrators block all SMTP access (usually port 25) or redirect all SMTP calls to their own server instead.   The available SMTP server might use IP authorization but fail because of an attempt to login.  Again, these changes were rarely explained to customers or support staff resulting in more confusion.

Little wonder some people pay for separate SMTP services just so that can reliably send out messages.  However, aside from cost, those services have issues regarding email domain confirmation and anti-spam filtering.  It’s best to send your messages out using the SMTP server chosen by your mail host.

Happily, many of these troubles have mostly gone away.  Any reputable ISP should now allow login from anywhere.   Hotel internet access should allow SMTP connections.  Note that we said should – there’s bound to be exceptions.

Ideally, a roaming user (really, any user) should be able to add SMTP login (as shown above) and use the computer anywhere they are in the world.   With people using tablets and smartphones (not just laptops) this has become a lot more common.

Fallbacks/workarounds

If you’re on the road and can’t send email there’s a few things you can try.

Test Account Settings

Go back to Outlook’s Test Account Settings for the account and see what happens.   Sadly, Outlook doesn’t easily show the error messages, it just tells you if the test worked or not.

VPN

A VPN connection will bypass any block on SMTP imposed by a hotel or other Internet connection.  There’s many VPN services available and they are a handy addition to any roaming users toolbox.  We currently use Witopia.

Demand better service and documentation

If you can’t find out how your ISP’s mail is setup, complain (politely but firmly).  There’s no excuse for poorly documented mail hosting and SMTP settings because it’s an important part of what you pay for.

If it’s a real problem, consider changing your email arrangements.   Using mail services from your ISP isn’t the best choice since there’s much better options available these days.   It’s a big step but with a modern mail host either free (Gmail, Outlook.com, Yahoo) or low-cost (Office 365 mail hosting or other Exchange Server hosting) you’ll get many benefits … seamless mail connections from anywhere is just one of those advantages.


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