LarryHN,
Thanks for your reply.
1. Understand that you cannot "fix" anything and that you are not Apple support. What I am looking for are suggestions to an issue that I'm sure is not unique to my Apple MacBook Pro running iPhoto 11 (9.3.2), particularly with regards to sending email through iPhoto (NOT through Mac Mail).
2. While I can understand your assumption that this is not a software glitch (or bug) due to incorrect user settings, you'd would not be correct in your assumption. I am well aware of how to configure a mail client, as I've been doing so on all types of platforms (Macs, PCs, Linux, and Unix (before it was Linux)) for the past 20 years. The issue with iPhoto appears to be the authentication (or lack thereof) between the application an the mail servers (most notably Google Apps SMTP servers).
3. Yes, Little Snitch may be an issue in some cases, as could OSX's built-in firewall if it were misconfigured. However, Little Snitch is not the cultprit here, as I have configured it correctly and I've troubleshot that angle.
4. Regarding your suggestion to use Mac Mail as the client, that really doesn't address my question, nor does it solve my problem (which is sending mail through iPhoto directly.) I'd prefer not to simply work-around a marketed feature of this commercial software because it does not function. That may be a solution for some, but it not for me. I'd rather find...a solution.
(time passed....took a look into it later in the evening....)
With a solution in mind -- I think I may have found it. Thanks to "wtobiasjr" here:
https://discussions.apple.com/thread/2699095?answerId=17637554022#17637554022 (see wtobiasjr's entry)
Here's what I did:
- Remove all mail accounts from iPhoto
- Log into Google Mail (including Google Apps Mail - which I use) and enable the 2-way authentication feature. This can be somewhat confusing, but go to this link and follow the guide: http://support.google.com/accounts/bin/answer.py?hl=en&answer=185833
- You'll need to create a password code and name it "iPhoto Email"
- Once you generate the passcode, copy it to your clipboard
- Go back into iPhoto and go to Preferences > Accounts > Hit the '+' to add an account
- NOTE: Do not choose the Gmail email type, use the "Other" type
- Fill in your Full name, Email Address, Description, Outgoing Mail Server (use smtp.gmail.com), keep port 587, enter your Username (which is your full email), and finally enter the code from your clipboard
Give it a try and you should not get the connection error message when you send an email. I tested it with one photo, multiple photos, and with various email accounts. All worked flawlessly for me.
Good luck!
DRD2