Using Shadowmail with GMail accounts

Using GMail accounts with Shadowmail

“Shadowmail” is a service for Sailmail members which monitors a separate email account via POP3 access. This post describes how to use Shadowmail with Google’s GMail accounts. GMail POP3 email access is a bit “quirky” (some would say “distinctly odd”).

The three great things about Gmail are that it is free, you get lots of space, and of course great search tools for archived email. The “quirky” part is that, depending on your GMail settings (see below), POP3 can try to forward everything in your GMail account, not just recent mail in your “inbox”. That is a problem if you have a large number of archived messages in your GMail account (which may be the whole point of GMail). If you pick the wrong option in setting up GMail’s POP3 access, then Shadowmail will try to send headers for a all of those messages. This is bad, so please read the following carefully.

Setting up Shadowmail access for GMail involves three steps:
1. Enabling POP3 access via settings in your GMail account;
2. Entering your Gmail login info into Airmail’s Shadowmail settings;
3. Resolving any GMail security issues to allow Shadowmail access.

One caution: Do this when you have internet access, and be sure that your internet connection allows Airmail to access Sailmail. See the post : “Connecting to SailMail, using AirMail, via the Internet” for more info.


Step 1: Setting up GMail for POP3 access:

First you need to enable POP3 access from GMail. Go to your GMail account, click “settings” (upper-right) and select the “Forwarding and POP” tab. In the “POP download” section you can enable POP access either for “all mail (even mail that’s already been downloaded)”, or “only for mail that arrives from now on”. That first setting is the problem if you have a lot of messages in your GMail account. So we strongly recommend checking the second “from now on” box. In this case only new messages, received after you enabled POP download, will then be available to Shadowmail. You probably also want to select “Keep GMail’s copy in the inbox”, it doesn’t matter for POP3 access but does effect how new messages are presented on the GMail web page.


Step 2: Airmail settings for Shadowmail:

The basic Shadowmail setup for Airmail is the same as for any account: The server-address is “” (without the quotes), the login name is your complete email-address (see below for the “recent:” prefix), and the password is your Gmail account password. A secure connection is required via port 995 but Shadowmail handles that automatically.

There is one more option: If you did select “all mail” in your GMail settings, then you can restrict POP3 access to only recent messages (less than 30 days old). Do this in your Airmail setup, by adding the prefix “recent:” to your login name in your Shadowmail settings– for example enter the login name of “” instead of “”– no spaces. This will cause GMail to only show recent messages to Shadowmail, and older messages will be ignored.

Keep in mind that (no matter what options are selected) GMail’s POP3-access includes sent-messages which were sent from GMail’s web-page. Also, unless you are using the “recent:” login-prefix described above, messages which have been read via GMail, or retrieved via POP3, are NO LONGER included in the POP3 index- they will disappear from your Shadowmail folder, but are accessible via GMail. However if the “recent:” prefix is used, then all recent messages are available to Shadowmail. (Like we said, “quirky”).

Once you get your Shadowmail settings set up for your GMail account, then connect to Sailmail (via internet, initially) and Airmail will send the settings message to the server. Shadowmail will immediately check your GMail inbox, and you should get back the initial batch of “new mail” messages which will sync your gmail “Shadow Folder” to your GMail account.


Step 3: Resolving GMail security issues:

Instead of a batch of “New Mail” messages, you may get an error message instead– have a look in “Shadow archive” folder under Airmail’s “Inbox”.

If you have entered the incorrect username or password then you will see:
[AUTH] Username and password not accepted.

Alternately you may have run afoul of GMail’s security checks, in which case you will see a message soemthing like this:
Exception while connecting: [AUTH] Web login required:

That is stunningly unhelpful, but if you follow the link then you will get some vague advice about “clearing the CAPTCHA” or maybe changing your password.

Here are the detailed instructions for fixing this:

First, you need internet (web) access. If you are trying to set this up via radio then disable the account until you have internet access: UN-check the ‘Account Active” box in Airmail’s Shadowmail Settings box, and connect to Sailmail to send the settings message.

With web access, the next step is to follow the instructions in the GMail error message and “Unlock the GMail CAPTCHA”. (A “Captcha” is that goofy “enter this text” box you sometimes see when you sign in via web). Either follow the link in the error message (above) or go directly to this web page:

You will need to log in with your Google username and password.
That takes you to a page titled “Allow access to your Google account”.
Click the “Continue” button.

Now go to Airmail and re-enable your GMail account in Shadowmail settings:
1. Open Airmail’s Shadowmail settings (Tools menu)
2. UN-check the “Account active” box. This creates a new settings message.
3. Connect to Sailmail (preferably via internet) to send the settings.
4. Go back to Shadowmail settings and CHECK the “Account active” box.
5. Connect again to Sailmail, to send the updated settings message.
This disables and then re-enables Shadowmail, forcing a new-mail check. Be sure to connect to Sailmail via internet each time, to send the updated Shadowmail settings message.

Wait a minute or two and check Sailmail again– you should have a batch of “new mail” messages.

If you still get an error message, then you need to get into your GMail account settings and authorize Saildocs access. Proceed as follows:

1. Open a web browser and sign in to your GMail account.
2. Open the settings window (the “gear” icon in the upper-right).
3. Select “Accounts” from the tabs across the top of that page,
4. Find “Change Account Settings” and click on
“Other Account Settings” (or “Google Account Settings”).
5. On this page click on “Security” (at the top).
6. You may see an “unusual activity” listing, with Saildocs listed.
If so, click “That was me”.
7. The second box on the left is “Account Permissions”, click “View All”.
This page lists all authorized devices and websites.
8. Look for “” there, if found then click “Allow access”.
(The IP address is
Then repeat the steps above to disable and re-enable Shadowmail.



As with other web-based email accounts, keep your Inbox tidy by archiving messages that you want to save and delete the rest. Gmail does not provide separate archive folders but you can add labels which is basically the same thing.

Revised 2014-03-03