Stuck sending email from a hotel or other blocking environment? Here's a solution when others fail

Note: This blog post is from 2007. Some content may be outdated--though not necessarily. Same with links and subsequent comments from myself or others. Corrections are welcome, in the comments. And I may revise the content as necessary.

Important Update

Well, I have to report some news since learning of this and posting about it. It turns out that this approach has the unfortunate side-effect that it makes your note go out as "from" your gmail account--even if you sent it as "from" another account in your mail client. That's a real bummer. Again, perhaps better than nothing, but not what I'd expected. On the surface, it may seem only a nuisance. If you read your gmail mail with your mail client (via POP), then you may not even notice this. But I did notice that the "to" address on replies sent while using this was my gmail address, which is not what I'd expected. And I just checked, and indeed the recipient also sees the email as coming to them "from" your gmail account. If either is a concern, then be aware.

There is a real gotcha, though, if you reply to a list. I had a note from a list that came, as expected, "to" my carehart.org address. When I replied, it would normally go back as "from" that address, which is the address on file at the list. But this change to the gmail address meant the note now went from an address not on the list. Some lists will bounce such notes, so you'll now it's happening (and now you'll understand why). But this list is one where if you send a note from a non-subscribed address, it just ignores it--so the note never got to the list. Only now did I connect the dots. Forewarned is forearmed!

You may not want to *always* do it, but when you're stuck in a hotel and need to get mail out, it's a blessing. I learned of it while traveling at the WebDU conference in Australia and after the conference was staying in a small hotel that was blocking my email. i couldn't get their smtp server address to use instead (more on that below), but using gmail as the smtp server worked!

Here's the blog entry that clued me into the solution. Many thanks to him.

As for how to configure your mail client to this up, the blog entry above gives the basics. You just want to change the SMTP (outbound) setting to use smtp.gmail.com, and port 465 (telling it to use SSL). You also want to configure the login authentication (for sending mail only) to be your gmail account. If you're really not sure how to change your mail settings, this trick may be above your level. But I will point out that Google themselves offer a page of info showing how to configure your mail clients. Just note that it's showing how to setup the client to both send and receive gmail. This trick is JUST about setting up to send email via gmail. Don't delete the incoming (pop) mail settings in your email client for your mail connection.

One last point about the option above: you do need to configure Gmail to permit POP access, as discussed here. But note that you don't HAVE to use pop (meaning a mail client) if you prefer to keep reading gmail via its web interface. If you never connect via pop, it will still be accessible via the web. Also, notice that even if you do collect it via pop (as I do), there's an option there to keep the mail in Gmail's inbox, if you prefer, so it's till always accessible via the web (though the web interface has no way of marking mail you read on your mail client).

Here's one other benefit of this approach of routing email through gmail: have you ever gotten bounces when sending mails because the recipient's mail server says yours is blocked in the "relay blacklist" or similar? This can happen on a hosted mail server because some chucklehead on the same server is involved in spamming, and gets your entire SMTP server detected as a spam source. Using this gmail approach would seem to prevent that (though I suppose some day some idiot will find a way to cause gmail's server to be blacklisted--but they'll certainly be a lot faster to address that than your average hosting provider, I think.)

What are some of the other solutions? Well, here's one entry on some alternatives and following is why they didn't work for me. Still, if you don't use Gmail (or don't want to use the approach above), they're worth noting:

• Get the hotel (or ISP) to tell you the name of the mail (SMTP) server they prefer you to use, and use THAT in your mail client. Sadly, it's not always possible to get that from the hotel or client staff.
• Use a webmail interface instead. There's almost always one provided by your email provider, and beyond that there are tools that will serve to do it for you even if yours does not (like www.mail2web.com). But I much prefer to have all my mail (in and out) saved in my mail client, both for archival and searching purposes.
• Use a 3rd party mail relay service, like smtp.com and smtpanywhere.net. If I hadn't found the gmail solution, I was about to do this. Couldn't find any that are free.
• Use a tool like JiWire HotSpot Helper, which does mail relay and more (like enabling secure email login and transmission, which is more important than many realize), but it's not free (there is a free trial).
• Use SSH tunneling, as discussed in a nice write up. Unfortunately, I tried it and my mail host doesn't support it. I've asked them.
• (Added since original post) Since only port 25 specifically may be blocked for you, you may find that your mail provider offers an alternative port to use to collect email. Mine does not, though as above, I have asked. (This was mentioned in the article I pointed to, but I didn't think to bring it up here in this list. A couple of commenters wanted to stress it as an option, so I'm adding it.)

If there are any other solutions I've missed, please do share. Hope this helps someone.

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