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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 Some content may be outdated--though not necessarily.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.
Hope this may help others. If you're in a situation where you find you can't send email out of your mail client (like Outlook or Thunderbird) because the ISP (or hotel, or client location, for instance) is blocking all outgoing mail (SMTP and the default port of 25), you have a couple of solutions. The common ones (more below) weren't working for me, but I found this gem. Did you know that if you're a gmail account holder, you can setup your mail client to use gmail's mail server to route your outgoing mail through? Yep. It really works, and saved my bacon today! :-)

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.

For more content like this from Charlie Arehart: Need more help with problems?
  • If you may prefer direct help, rather than digging around here/elsewhere or via comments, he can help via his online consulting services
  • See that page for more on how he can help a) over the web, safely and securely, b) usually very quickly, c) teaching you along the way, and d) with satisfaction guaranteed
Comments
For anyone using HostMySite for their email, they have their mail servers configured to listen on port 50 as well as port 25. Configuring your mail client to use port 50 can sometimes get around the hotel's policy. Leo hints at this in the page Charlie links to.
# Posted By Sean Corfield | 3/24/07 1:00 AM
Thanks for raising that point, too, Sean. I should have mentioned that I'd tried the port 26 that the article refers to, but it didn't work, and I've asked the host if they have such an alternate port (when I asked about SSH as well). We shall see. But yes, it's an option others should look into as well.
# Posted By Charlie Arehart | 3/24/07 9:22 AM
And if you happen to run your own mail server (we use smartermail), always set up an alternate port. I find some places block 25, others lock down everything except for maybe 25, 80 and 443, but if you have both 25 and an alternate, you can usually send emails. Worst case, webmail as a backup is your friend. On a related note, if IM is blocked, a web IM like Meebo works well.
# Posted By Peter Bell | 3/24/07 12:51 PM
Thanks, Peter, but it seems you may have replied without noticing the comments above from Sean and me on that subject. I'll update the entry to avoid further confusion. :-)

Also, I have to share some bummer news: it seems that doing the approach that the gent suggested (routing through gmail) had the unfortunate side-effect of making any reply come back to the gmail account--even if you sent it "out" from another account in your mail client. Bummer, bummer. Again, perhaps better than nothing, but not what I'd expected. I'll update the entry for that as well.
# Posted By Charlie Arehart | 3/24/07 7:15 PM
Hi Charlie,

Sorry - was in a bit of a rush this morning so I didn't read properly. BTW, great to see your postings from WebDU. I hope you're enjoying the late summer sunshine before you return to the US?!
# Posted By Peter Bell | 3/24/07 7:36 PM
Thanks, Peter. Actually, after I wrote that entry about how hot it was, a storm blew in and it's been rather chilly (feels like 60's, Fahrenheit) and quite windy, since last evening. I was even caught out in the leading thunderstorm, out in a large park with no enclosure. I tried to use some trees for cover, to no avail. I was soaked for the evening.

Back to the subject of the entry above, I have also added clarification that the means by which it changes the from address is also a killer if you're responding to a list--where the list may not accept your message now from a non-authorized address. Again, bummer! Or for my friends in Oz, the UK, and such, bugger all! :-)
# Posted By Charlie Arehart | 3/24/07 8:21 PM
:->
Well, sorry to hear of yoyr brush with the inclement Australian weather. I never really think of Sydney as land of the thunderstorm, but I guess that just means the tourist convention are doing their jobs!

I'm hoping to catch WebDU next year - travel, ColdFusion and surfing - I'm sure it'd be a cool trip!
# Posted By Peter Bell | 3/24/07 8:39 PM
You can set your Gmail account up so it sets the reply-to as your regular email address and then emails sent out via Gmail will appear to be from your regular address - and replies will route back to that address. I set Gmail up for a couple of people that way.
# Posted By Sean Corfield | 3/24/07 9:06 PM
You might change from port 25 to port 587, as defined by RFC 2476 for the use of roaming users.
# Posted By secure email | 4/8/07 10:31 AM
Most computers are configured to use the DNS of the ISP. All you need is to have a quick look-up at the DNS number that your connection uses. Copy and paste primary and secondary DNS numbers in google... you will get the name of the ISP. Then search in gg again the smtp of the ISP and you can add it to your smtp list in thunderbird (use extension named smtp select under thunderbird for more comfort).
Of course it still happens than the hotel blocks completely the port 25 in which case the management of the hotel should change that setting.
# Posted By cocoleharicot | 8/18/11 2:55 AM
I work for a managed solutions provider for hotels and other hospitality hotspots. We provide all the internal routers, switches and wifi equipment to the hotels, and manage and support them. I would just like to point out that the issue here is not with the hotel's equipment or with hotel policy, but the ISP's policy. Internet service providers like ATT, comcast, etc. will block IP addresses where spam is known to have come from in the past. They use blacklisting services from companies like Barracuda and Cisco to identify these IP addresses. If the hotel is blacklisted, the hotel's ISP is the one blocking it, so more often than not the hotel will be totally unaware unless its become a major point of contention between their guests and their staff.

Finding out who their ISP is and using their ISP's outbound mail servers will often solve the issue. (ie: if they use ATT for their ISP, then mail.attbi.net will work as an SMTP server while you're in the hotel)
# Posted By Dan | 7/31/13 12:15 PM
@Dan, thanks for sharing the information, given your background which is so relevant (to this now-7-year old blog entry). Hope it may help future readers.

I would note though, to your last point, that I did propose the same (in effect) as the first bullet in my list of things to try, to solve the problem. That said, if the hotel didn't know the SMTP server to try, your point would seem that we could/should find out what ISP the hotel does use and then try the mail server for that.

I suspect a lot of folks would still be stymied at that point :-), but certainly it's worth noting in case it may help someone. Thanks.

PS These days when I am in a hotel, I generally just use my mobile phone as a mobile hotspot for use with my laptop and mail client, to it's not really an issue I've hit in years myself.
# Posted By Charlie Arehart | 8/1/13 12:13 AM
A simple solution is Travel SMTP (www.travelsmtp.com), works in every hotel and you never have to change your settings again. I use their service for over 2 years by now and I never have problems with sending email anymore. They even have a firewall-proof setting, it's cheap and the service is great. I can recommend it to everybody.
# Posted By Joshua | 8/16/13 9:44 PM
@Joshua, interesting. Thanks for that.
# Posted By Charlie Arehart | 8/21/13 1:44 PM
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