Outgoing Mail Blues Revisited
Posted on Saturday, August 19th, 2006 at 10:06 pm under On The Road.
A year ago I did a tutorial on how to resolve the pesky outgoing mail issues that come up when traveling with a laptop. The problem comes from the fact that many ISPs do not allow you to send email unless you use their SMTP server. This is fine if your computer does not leave home, but it is irritating if you go back and forth from home, or work, or a coffee shop or a hotel.
In this tutorial we’ll set up a GMail account and use it’s servers to send emails from Mail regardless of where you are connecting from. It should be easy to apply the same settings to Entourage but I am not covering that on this tutorial. Although I am using Tiger in this example, it is not required for it to work.
The process in my previews tutorial involved finding your ISP though Network Utility, looking up the SMTP online and then entering the new SMTP server on your mail application. It was a long process to solve the issue but at the time it was the only way I knew of. Since then a new application has come out that atomizes part of the process. WiFiSMTP finds the SMTP servers automatically. This is great in theory but I have tried at four different locations during my road trip and none of them have worked. So what do we do then? Thanks to a tip from my friend Steve, I am now sending email from any place on earth without having to do anything by using Google’s GMail services.
Step 1: Get a GMail Account
Ok, if you don’t have one already, this step might be the hardest one since Google still has GMail in beta. GMail accounts are invite only. So if you know someone who has one(wink, wink), have them send you an invitation to join.
Step 2: Set Up GMail for POP
Using your browser, login to your GMail account at gmail.com then go to the settings page by clicking on the setting link in the upper right corner of the page. From the settings page, select the Forwarding and POP tab then enable POP for all mail from the POP download section. Enabling POP allows you to use a desktop application like Mail or Entourage to check and send GMail mail but in our case, we’ll use to be able to send mail from our another account.
Step 3: Change GMail’s Sending Email Address
Go to the accounts tab and click on Add another email address then enter the email address that you would like your emails to come from. This should be an email you already have in your Mail application. Once the email address is confirmed by email, return to this same page and make that email address the default one by clicking on the make default link that corresponds to the email address you just added.
Step 3: Add GMail’s Servers to Mail
From Mail, select Mail > Preferences then select the Accounts tab.
From the accounts tab, select your account and go to the Account Information tab. From the Outgoing Mail Server(SMTP) pulldown menu, select Add Server to add the GMail server settings.
From the new window, add the following settings:
Outgoing Mail server: smtp.gmail.com
Server Port: 587
Use SSL: yes
Authentication: Password
Username: your GMail username
Password: your GMail password
Once created select the GMail server from the Outgoing Mail Server(SMTP) pulldown menu and close the preferences window.
Conclusion
This technique allows you to send email from Mail wether you are at home or at the local Starbucks without having to do anything at all. If you want to also check your GMail email from Mail, Google offers a wonderful tutorial on it.
Aug 20th, 2006 at 2:12 am
Basically, most ISPs SMTP servers authenticate by IP address. If you’re in one of their IP ranges they allow you to send through their mailserver. However, some ISPs will allow you to authenticate by a username and password (SMTP auth) so that you can send from any IP address.
Another alternative if your ISP doesn’t provide SMTP auth is, if you have a home server you can set up a mailserver there that relays to your ISPs mailserver and then set up SMTP auth on your home mailserver.
Aug 20th, 2006 at 2:50 pm
Actually, I think that this solution works because it’s NOT using port 25. Most ISPs block port 25, thus having a mailserver at home answering on this port won’t due much good (though you could move it to 26 or, even better, 80).
However, being that google offers SSL SMTP, you’re using a different port that isn’t (currently) blocked by ISPs. (Since SSL SMTP implies authentication (though not necessarily), ISPs probably won’t bother blocking it.)
Aug 20th, 2006 at 7:26 pm
-wow-
This is binary gold!
Thank you for publishing this.
~Miscellt
Aug 21st, 2006 at 5:25 am
Although this solution is usually workable, there is a hitch. Here is the problem I face… my employer provides an SMTP address as well as an IMAP address in order to allow us to set up our work e-mail on our personal laptops if we so desire. I had set mine up with the IMAP server for both sending and receiving e-mail. I have two different residences. While the IMAP server setting worked completely fine for both sending and receiving from one residence, it did not work for sending mail from the other residence. I tried using the SMTP server (again, from work) for sending but this didn’t work as well. I called my local internet provider about this problem and they told me to set up my SMTP server to use their ISP (similar to what you suggested above).
When I did this, I was able to:
(1) receive e-mail - which was never a problem to begin with
(2) send e-mail using my ISP’s SMTP server (as expected).
However, there were two problems:
(1) I could not send e-mail using this server if I wasn’t at this residence (as expected based on what you’ve written
(2) If I sent e-mail using the SMTP server of my ISP, and sent it internally to someone at work, my WORK server would reject it… essentially the e-mail would seem to me as though it had been sent, I would never get an undeliverable message and the message would disappear into cyberspace forever, not having reached its recipient. I’m guessing the reason for this is that the work server cross checked to see if the e-mail address (my work address) matched the sending server’s address - as a way to block out spam.
Any suggestions for getting around that one? I suspect it doesn’t matter whether I use my ISP’s SMTP or Google’s but as long as it’s not my employers, it won’t work for sending internal e-mails.
And of course I can’t use my employer’s servers to send mail from this location because the ISP won’t allow it…
Aug 21st, 2006 at 11:47 am
NB, your workplace will have to do what Google does, and use an alternate smtp port for you to send through them. They must have one already set up if anyone else is sending email from outside their office.
Sep 3rd, 2006 at 2:50 pm
I just found this page:
http://www.dan.co.jp/cases/macosx/tiger/postfix-tiger.html
which has an interesting alternative solution, to run sendmail-type apps on your own laptop. I think I’ll be trying this…
Sep 7th, 2006 at 1:12 am
This isn’t about the topic at hand, but because there’s so many mac gurus here i thought i might ask. i’m looking for a program to simply password protect folders. there are a fwe people that get on my computer every now and then and i would like to password protect some folders so that they cannot access them. I’m just looking for a simply password prompt box to pop up and i enter the password. does anyone know of anything like this? or where i could look? thanks!
Oct 6th, 2006 at 6:25 pm
Didn’t work on my Mac, maybe because of my ISP…
Oct 6th, 2006 at 11:43 pm
Yep, this did the trick. In my case I did not have to switch on the SSL checkbox. (Using GMX)
It took me 5 days to figure out this problem. My provider, BigGlobe NEC did not repond to any of my support emails. Screw them!
Nov 2nd, 2006 at 5:09 am
I cant belive it. Tis is perfect. I’ve been trying doing something like that for months.
Thank you very much
r
Dec 4th, 2006 at 11:41 pm
Thank you so much for this solution.
Dec 14th, 2006 at 7:23 pm
Here’s a catch (I didn’t see it covered): When you use GMail’s SMTP servers, when you reply, it will reply directly to your gmail account. A little annoying.
Jan 18th, 2007 at 2:52 am
Jason is right in that mail will always appear to come from the google account, but if you have the option to add a ‘reply-to’ address, then this will be used.
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