Hi all.  I have read the FAQ entry at
https://www.enigmail.net/index.php/en/faq?view=category&id=11#faqLink_2
and while my problem is related, it was not resolved by the steps
there.

I am using gpg 2.1.13 Enigmail 1.9.5 and Thunderbird 45.3.0 on a MAc.

When I choose an encrypted email in Thunderbird, it displays a blank
preview page, no prompt for passphrase. When I cache my password by
using gpg on the command line, then it decrypts.

I am using pinentry-mac from homebrew and symlinked pinentry to it. My
gpg-agent.conf file includes
pinentry-program /usr/local/bin/pinentry-mac

The pinentry example and the gpg-connect-agent GET_CONFIRMATION
example in the FAQ entry both work for me.  When I run gpg-agent with
debugging, I observe the following:

gpg-agent[7155]: WARNING: "--use-standard-socket" is an obsolete
option - it has no effect
gpg-agent[7155]: enabled debug flags: command cache ipc
gpg-agent[7155]: listening on socket '/Users/tritter/.gnupg/S.gpg-agent'
gpg-agent[7156]: gpg-agent (GnuPG) 2.1.13 started
sh-3.2$ gpg-agent[7156]: handler 0x700000081000 for fd 5 started
gpg-agent[7156]: DBG: chan_5 -> OK Pleased to meet you
gpg-agent[7156]: DBG: chan_5 <- RESET
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- GETINFO version
gpg-agent[7156]: DBG: chan_5 -> D 2.1.13
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- OPTION allow-pinentry-notify
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- OPTION agent-awareness=2.1.0
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- OPTION pinentry-mode=loopback
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- AGENT_ID
gpg-agent[7156]: DBG: chan_5 -> ERR 67109139 Unknown IPC command <GPG Agent>
gpg-agent[7156]: DBG: chan_5 <- HAVEKEY AAAAA
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- HAVEKEY BBBB CCCCC DDDDD EEEEE FFFFF
GGGGG HHHHH IIIII JJJJJ KKKKK AAAAA
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- HAVEKEY AAAAA
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- RESET
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- SETKEY AAAAA
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- SETKEYDESC
Please+enter+the+passphrase+to+unlock+the+OpenPGP+secret+key:%0A%22Tom+Ritter+<t...@ritter.vg>%22%0A4096-bit+RSA+key,+ID+03FFC8624E256AB8,%0Acreated+2016-08-15+(main+key+ID+66A109189B79658F).%0A
gpg-agent[7156]: DBG: chan_5 -> OK
gpg-agent[7156]: DBG: chan_5 <- PKDECRYPT
gpg-agent[7156]: DBG: chan_5 -> S INQUIRE_MAXLEN 4096
gpg-agent[7156]: DBG: chan_5 -> INQUIRE CIPHERTEXT
gpg-agent[7156]: DBG: chan_5 <- [ aa bb cc dd ee ff gg hh ii jj kk ll
mm nn oo pp ...(539 byte(s) skipped) ]
gpg-agent[7156]: DBG: chan_5 <- END
gpg-agent[7156]: DBG: agent_get_cache 'AAAAA' (mode 2) ...
gpg-agent[7156]: DBG: ... miss
gpg-agent[7156]: DBG: chan_5 -> S INQUIRE_MAXLEN 255
gpg-agent[7156]: DBG: chan_5 -> [[Confidential data not shown]]
gpg-agent[7156]: DBG: chan_5 <- [eof]
gpg-agent[7156]: failed to unprotect the secret key: End of file
gpg-agent[7156]: failed to read the secret key
gpg-agent[7156]: command 'PKDECRYPT' failed: End of file
gpg-agent[7156]: DBG: chan_5 -> ERR 67125247 End of file <GPG Agent>
gpg-agent[7156]: Assuan processing failed: Broken pipe
gpg-agent[7156]: handler 0x700000081000 for fd 5 terminated
gpg-agent[7156]: handler 0x700000104000 for fd 6 started

Strangely, all the items I replaced with AAAA etc are not in my
keyring.  Checked by doing gpg --fingerprint --fingerprint --list-keys
| grep AAAA (with the first 4 octets of each key).

-tom

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