GMail App Specific Passwords for Mac Mail

I personally got tired of struggling with numerous mail clients over the years and have now been happily using Gmail through the browser (using Google Authenticator for 2-factor) for years now. Gmail, Outlook.com and even Yahoo mail have come a long way in usability over the last few years.

My first thought is that this isn't an issue related to app specific passwords at all. To Mail and keychain, I can't imagine that there is any difference in a typical password and a Google app specific password. That difference is only on Google's end. Therefore, you will likely have issues even if you turned off two-factor on your Google account (a bad idea as you understand). To prove this to yourself you could create a throwaway google account, without 2-factor turned on, and see if you can get that account to work with Mail. I bet you will find the same troubles.

It's unfortionate, but I have read enough troubled posts over the last year to make me recommend anything but trusting Apple Mail and it's interaction with Google accounts. The issue is obviously a combination of Google's non-standard implementation of IMAP and Apple Mail's inability to cope with it. That doesn't quite make sense to me because Mail on iOS seems to work just perfectly with Gmail accounts (including with app specific passwords). Just not on the Mac OS X version of Mail.

Either way, I need my email to be reliable and predictable and therefore I now find myself just using the browser for webmail even after years of saying that I would never use webmail over a client application. I'm now far more productive that I ever was with a local email client and I can move from computer to computer with no setup or configuration required.

Good luck with your search for an alternative Gmail client.

Yes, I currently use three Gmail accounts (regular Gmail and Google Apps both) and 5 Gmail calendars, from my iPhone (iOS 7) without any issues at all. All of them use app-specific passswords. They all work reliably and are stable.

On all laptops and desktops I use my Gmail accounts through the browser (Chrome is my browser of choice). The only annoyance is that you do need to login to each separately. But, Google has now streamlined that a bit and on logout it will list your multiple google accounts for easier login. You can use Google Authenticator on your phone to increase your browser email login security via Google 2-factor that you already have enabled.

One last suggestion is to consider consolidating your many email accounts by funneling them into fewer accounts by using their forwarding options. I also have far too many email accounts but I have the majority of them set to forward into the few accouts that I check. You can even set up Gmail to allow you to "send as" those accounts. And lastly, you can use Gmails "Filters" to apply labels to each of those forwarded account emails so they are color coded and can be instantly filtered by clicking on the label in the Gmail sidebar.

I wish you luck in your quest to tame your email.

what is the reference to Google Apps? you are saying here that you access your three GMail Email Accounts from GMail on the web (presumably on your computer) and you access these three email addresses on your iPhone using the GMail app?

Yes, I use Chrome browser from several computers to manage several gmail accounts and I use the Apple Mail app from my iPhone for those same accounts. The only real difference in a Google Apps account is simply that it has a real domain name associated. On the iPhone is where I use the app specific passwords.

how you use the Google Authenticator? i seem to use this nicely when i get a PROMPT for something from GMail but if i try to use this generated password in MAC MAIL or in SPARROW or something else it does not take

Google Authenticator codes are used for logging in through the browser only. A given code changes ever minute and can't be used for mail clients.

Google app specific passwords are still used for any mail client like Apple Mail, Sparrow, Thunderbird, Outlook, etc. on Mac OS. App specific passwords are also still used in Mail on iOS. App specific passwords do not expire like authenticator passcodes and therefore you don't need to change email client passwords after they are set up. You should use a different app specific password per device because you can cancel a single app specific password at any time if you were to have a lost iPhone for example.

The Google single use passwords are ONLY ever used if something goes really wrong and you don't have you iPhone and therefore can't generate an authenticator code when needed to login to webmail.

OK. i caught that Send As option at one point. this is if you log into the website, yes? also, the Filters means that you color individual EMAIL ADDRESSES in GMail website and then you can easily see which email in the UI was sent to which email address?

Yes, login to a Google account through the browser and click the "Cog" > "Settings" > "Accounts" > "Send mail as". In that section you can add your other email addresses that you may want to send mail as right from this single Google account. Once set up (and confirmed) you will be able to choose a "From" address when in the compose dialog.

Yes, you can set up a Google "Label" for each email account that you are forwarding in. Then, set up a "Filter" that applies the right label to all incoming emails from that account. You may then need to go into the label display settings and make sure that all your lables are displayed on the sidebar. The easy way to learn filters and lables is to try creating a label for a specific person you get email from and then create a filter to apply the lable to all of their incoming emails.

Lables are simply categorization tags that allow you to quickly query a specific set of email in your Google account. There are no real folders of any kind in Gmail, just labels. Clicking a label in the sidebar simply executes a databse query to display only those messages. The other benefit is that you can change the colors to have a visual que for messages with one or more lables applied as well.