It certainly looks like it has something to do with the double Primary Password prompt: - if I enter my primary password once, and dismiss the second PP prompt, then the first email I send fails to sign, with "no cached password", but the second email I send signs fine. - if I enter my pp twice, once to each prompt (one per window), then the first email I send signs fine. What's odd is that entering my pp only once, and dismissing the second prompt, doesn't cause a problem for anything else: I am still able to access all my IMAP & SMTP accounts, whose passwords are stored. And of course it's my belief that TB shouldn't only prompt me *once* for the primary password, regardless of how many windows open at startup. I will continue to test having entered the primary password twice, once for each prompt, and see if I get any failures at all.
Bug 1764175 Comment 16 Edit History
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It certainly looks like it has something to do with the double Primary Password prompt: - if I enter my primary password once, and dismiss the second PP prompt, then the first email I send fails to sign, with "no cached password", but the second email I send signs fine. - if I enter my pp twice, once to each prompt (one per window), then the first email I send signs fine. What's odd is that entering my pp only once, and dismissing the second prompt, doesn't cause a problem for anything else: I am still able to access all my IMAP & SMTP accounts, whose passwords are stored. And of course it's my belief that TB should only prompt me *once* for the primary password, regardless of how many windows open at startup. I will continue to test having entered the primary password twice, once for each prompt, and see if I get any failures at all.