Using Gmail as your SMTP server When Using your ISP's Email

NOTE: You’re going to be using Google’s service to send the email but for all intents and purposes it’s completely transparent to both you and your recipient. It’s also a world lot better than using some random SMTP server (having to find out the local one and always change it) or finding all your email you sent doesn’t even arrive in your recipient’s inbox because it’s been marked as spam because of the server used. I’d recommend looking for an IMAP host instead for the long run.

For brevity I’m leaving out the exact steps to hook this up with your favourite mail client but you can find that out fairly easily as it’s only changing the SMTP server (or check my post about setting up Shaw’s SMTP service) and change mail.shaw.ca to smtp.gmail.com and using your Google login instead of say Shaw’s in the section about changing your SMTP server).

  1. Set up a Google Account. If you have one you’re good to go.
  2. Log into Gmail
  3. Go to Settings (link is in the top right)
  4. Go to Accounts and Import
  5. Under “Send mail as:” section click “Send mail from another address”
  6. Enter your email address you want to use (eg. [email protected]) and press Next
  7. Choose to use Gmail’s servers, press Next and choose Send Verification
  8. Click on the link in the verification email. This will verify the email address so you can move onto step 9. You may need to check your Junk Mail folder.
  9. Back at the “Send mail as” section (you may need to refresh the browser) click the “make default” link for the email address you set up and be sure that below it “Always reply from default address” is selected.
  10. Now be sure to change your SMTP settings on your computer/mobile device accordingly. This varies from device to device as to the steps but is the most important step. If not set correctly (eg. not turning off other SMTP servers on an iOS device) will make everything we’ve done for naught.
  11. Send an email to yourself to test and reply to it and make sure it gets to the right address. The only times I’ve ever seen an error here is if the SMTP wasn’t set up correctly, step 9 wasn’t followed or the carrier’s SMTP server was enabled again (yes it’s repeated because it accounts for 99% of errors I’ve seen).

Not difficult, but something I can grab when writing an email on how to do it. :-)

Hooking Up with Shaw's New "Remote SMTP" Service

Update (February 2012 - Webmail 2.0 is completely up with all it’s Exchange goodness - so check out Shaw’s new instructions )

Please join me in welcoming Shaw’s new feature of actually allowing Shaw email users to send email while travelling without resorting to webmail or trying to find the local ISP’s SMTP server address (or seeing that Telus' mobile SMTP server is blacklisted AGAIN marking all your email as spam). This is of course ignoring that I don’t recommend anyone actually use their ISP provided email address but instead use something a bit more dedicated like your own domain or an actual email service. It’s still better than an AOL address.

Previously I’d been setting clients up to use a Gmail account as their proxy sending address when they have a Shaw or Telus email address - this makes it easier for Shaw clients. It’s also a lot simpler than the Gmail approach (which I have yet to post here).

Coles Notes

  1. Turn on Mobile Access using the new Webmail beta: https://wmbeta.shaw.ca
  2. Change your SMTP settings to point to mail.shaw.ca using port 587, STARTTLS, and use your username and password as the authentication

More elaborate instructions

Setting Up Shaw’s End:

  1. Sign into https://wmbeta.shaw.ca
  2. Click on Preferences (right side of screen - it’s a text link beside Feedback)
  3. Click on the ‘tab’ that says ‘Mobile Access’
  4. Set it to Enabled (click the radio button beside it)
  5. You may need to change your password to meet their new security requirements.
  6. Press Save. It will say “Preferences saved” in a small yellow box at the top of the page if it’s successful.

Thunderbird:

  1. Go to the Tools menu and choose Account Settings
  2. On the left side on that window click on “Outgoing Server (SMTP)”. You may need to scroll as it’s always the last item.
  3. There should be an item associated with the Shaw account you just turned on. Whichever account you turned on Mobile Access for and click on it and then click the button that says “Edit…”
  4. In the window that appears change the server name to mail.shaw.ca instead of shawmail or shawmail.cg.shawcable.net that it was set to. The port number should be changed from 25 to 587 and the Connection Security to STARTTLS. Authentication: Normal password and then enter your username
  5. Press OK
  6. If you did not change your password when setting up Shaw then press OK and you’re done. If you did change your password when setting up Mobile Access the next time you check email it will ask you for a new password and you can enter it.

Mail.app:

  1. Go to the Preferences and click on the Accounts section
  2. Click on your Shaw account on the left side
  3. Where it says Outgoing Mail Server (SMTP): click on the drop down menu and choose “Edit SMTP Server List”.
  4. Find the Shaw SMTP server in that list and click on it.
  5. Change Server Name to mail.shaw.ca
  6. Click on the Advanced tab
  7. Check off Use Secure Sockets Layer
  8. Change the Authentication drop down menu to Password
  9. Enter your username and password and then press OK.
  10. Close the accounts preferences window and say yes to saving it if necessary.

Shaw’s already provided instructions on setting up an account anew for iOS, Android and Blackberry devices: https://wmbeta.shaw.ca/doc/offnet-device-instructions.html

Disabling Mail.app's To Do Mailboxes and Quasi-Debugging Mailbox Creation

Leopard’s Mail.app introduced some nice speed improvements over Tiger’s version but introduced one of the most annoying features (IMNSHO) in Leopard. System Wide “To Dos” in a garish Marker Felt font intent on polluting my IMAP mailboxes with Apple Mail To Do or ToDos.mbox seemingly placed randomly (they aren’t but when your Prefixes differ from account to account it seems random at first). Additionally when I moved servers at my host my accounts on my computer started misbehaving creating nested mailboxes continuously. In the end it’s mostly user error but I’m hoping these tips on how to disable the To Do mailbox (see the edit for the easy way) and force Mail to look properly for the right mailbox will help someone jump to the fix that will stick.

Mailbox Setup Reference

To start with for reference I have several computers and an iPhone that share 4 IMAP accounts (GMail, my webhost and one from work). The main reason I use IMAP is that it keeps them in sync - the backup on the server is just gravy. By default Mail.app uses a mailbox called “Sent Messages” and “Deleted Messages” for it’s Sent and Trash mailboxes. If they do not exist it will attempt to create them - which isn’t entirely interoperable with some webmail clients out of the box (eg. Squirrelmail and RoundCube don’t use those mailboxes by default) or other email clients such as Thunderbird (which doesn’t allow you to change your Trash mailbox in Account Settings so you can’t tell it to use Deleted Messages as well).

Changing Your Sent and Trash Mailboxes Normally

In Mail.app you can click on a mailbox (eg. Trash Man O' Doom) you’ve created and then under the Mailbox menu scroll down to “Use This Mailbox For” and set the mailbox for what you would like to use it for Drafts, Sent, Trash or as the Junk Mailbox. Nice, easy and it nearly always works. (I’ve had it not work once and that wasn’t Mail’s fault)

To Do Mailboxes Are From Hell

You may have noticed above that there was no option for a “To Do” mailbox or even an option anywhere to disable System wide To Dos which means that once iCal is opened or any To Do is intentionally or accidentally created Mail.app will dutifully create Apple Mail To Do mailboxes for each account you have following the IMAP Prefix if necessary. On my iPhone where To Dos are not even recognized it means I’m always seeing a completely useless Apple Mail To Do mailbox somewhere in the hierarchy of my mailboxes.

Following the publishing of a hint on MacOSXHints.com that described the key used in Mail.app’s Preference file (com.apple.mail.plist) I decided to go digging to see what else was stored there. I discovered that by setting the value to nothing (as in just leave it blank) that To Dos were effectively disabled on that account - I could then delete the Apple Mail To Do mailbox on the account. By doing the same change on the other computers (4 accounts * 4 computers = tedious) I was then Apple Mail To Do mailbox free!

**EDIT: According to a newly published hint there’s another way to avoid ToDo mailboxes being recreated by changing the NewNoteToDoAccount key to the ID of your local account. After deleting all my To Do mailboxes this was auto set so I didn’t notice that it had changed.

**EDIT 2: As far as I can tell this is akin to setting Create Notes & To Do’s in: to On My Mac in the Composing section of the Mail Preferences - which is FAR easier than messing with the plist file.

Multiplying Inboxes

When I changed servers at my webhost, Mail.app got confused about the IMAP Prefixes (I believe the new server was telling Mail.app INBOX and the old server was saying /, but I’m unsure) and decided to whenever I deleted a message to move the message to a new mailbox it would create at INBOX/Deleted Messages. Thinking it was an anomaly I would move the message where it should have gone and delete the newly create mailbox. The next time a message would be deleted (wasn’t necessarily on that computer) it would recreate that mailbox but oddly at INBOX/INBOX/Deleted Messages and the cycle would keep repeating. This was the one time that selecting the Trash Mailbox (Deleted Messages at / and not in INBOX) and telling it to use it failed.

Using the knowledge that the mailbox information is stored in com.apple.mail.plist I edited the offending section setting it properly and haven’t had a problem with it since - it was a good way of having somewhere to write in “I want my Trash to go here”. So it’s useful for making changes and checking to see what path that Mail.app is looking for when it shouldn’t be looking at that location (especially via SSH when VNC is unavailable).

So my frustration ends with that to edit a binary plist the only Apple provided tool is the new Property List Editor 3.0 which is not an optimum solution for editing - it doesn’t provide searching and I find that the extra work using plutil to convert to xml instead of binary and back so I can use TextMate not worth it in the end. Much of what you need to do is in Mail.app itself but when Mail.app is acting up, it’s good to know where you can go to set it back straight and stop the cluttering of your mailbox hierarchies.

iPhone Cryptic Error : Invalid Recipient

While I really enjoy my iPhone’s ease of use it does spit some really cryptic errors sometimes. Namely one I’ve kept running into after changing over my domains to the new Shared Accelerators from Joyent which changed my SMTP information.

For some reason my new SMTP information just wouldn’t sync to my iPhone correctly - at best the server info will but the username and password were blank. I’m not 100% certain that the error is not exclusive to Joyebt’s email servers as I have seen it on another server as well - but when the username or password is wrong when attempting to send uemail you are presented with the following error:

“One of the recipient addresses was invalid”

Frustrating and exceedingly cryptic, but if I write it down then I might actually remember what the error means next time.