Outbound Apple Mail Gmail Messages Trapped in Outbox

Question

Mavens,
On an iMac running Mavericks (OS X 10.9 (13A603)) and Apple Mail 7.0 (1822), outbound GMail messages remain trapped in the Outbox.
NOTE: This GMail account is using Google's 2-step Verification with an Application-specific Password for Apple Mail.
Apple Mail does access GMail's Inbox (it seems that all Gmail Inbox messages are reflected in Apple Mail's Inbox).
Outbound Gmail Emails remain trapped in Apple Mail's Outbox.
ALSO—
If Apple Mail is closed, then re-opened, it (Apple Mail) asks for the GMail password...over & over & over...the only solution I've found is to create a new Google Application-specific password. Very tedious, and quite un-Apple-like ("...it just works.").
If you've encountered—and fixed—either of these problems...what do you suggest? Any ideas?
Many, many thanks in advance.
Best,
Plane Wryter

Answer 1

May have found a fix!
Thrashing around in Mail | Preferences | Accounts...
I painstakingly worked through all the settings for the GMail account (e.g., double-checking IMAP and SMTP parameters).
In doing so, I notices that the setting for "TLS Certificate" was "None" (as it is for my other GMail accounts).
On a whim, I clicked the drop-down for TLS Certificate...and selected com.apple.idms.etc.etc.
Allons-y! It worked.
A moment after selecting the TLS Certficate setting...the [formerly] trapped Outbox Emails launched on their way.
If you have the same symptoms, I hope this helps.