Moved out from T4123:

In T4123#123782, @nbriggs wrote:

in I think a related scenario we are having the pinentry window not spawn at all, leading to "no pinentry" errors
Win 10 latest patches Mar 2019
Version 3.1.4-gpg4win-3.1.5
We've tried a few hacks including adding the .conf file to C:\Program Files (x86)\GnuPG\bin with
pinentry-program "C:\Program Files (x86)\Gpg4win\bin\pinentry-qt.exe"

C:\WINDOWS\system32>gpg --debug ipc -vK
gpg: reading options from 'C:/Users/nbriggs/AppData/Roaming/gnupg/gpg.conf'
gpg: enabled debug flags: ipc
gpg: using pgp trust model
gpg: DBG: chan_0x00000260 <- OK Pleased to meet you
gpg: DBG: connection to agent established
gpg: DBG: chan_0x00000260 -> RESET
gpg: DBG: chan_0x00000260 <- OK
gpg: DBG: chan_0x00000260 -> GETINFO version
gpg: DBG: chan_0x00000260 <- D 2.2.11
gpg: DBG: chan_0x00000260 <- OK
gpg: DBG: chan_0x00000260 -> OPTION allow-pinentry-notify
gpg: DBG: chan_0x00000260 <- OK
gpg: DBG: chan_0x00000260 -> OPTION agent-awareness=2.1.0
gpg: DBG: chan_0x00000260 <- OK
gpg: DBG: chan_0x00000260 -> HAVEKEY *KEY*
gpg: DBG: chan_0x00000260 <- OK
gpg: DBG: chan_0x00000260 -> KEYINFO *KEY*
gpg: DBG: chan_0x00000260 <- S KEYINFO *KEY* D - - 1 P - - -
gpg: DBG: chan_0x00000260 <- OK
gpg: DBG: chan_0x00000260 -> KEYINFO *KEY*
gpg: DBG: chan_0x00000260 <- S KEYINFO *KEY* D - - - P - - -
gpg: DBG: chan_0x00000260 <- OK

C:/Users/nbriggs/AppData/Roaming/gnupg/pubring.kbx

sec rsa2048 2019-03-25 [SC] [expires: 2021-03-25]

---

uid [ultimate] Nathan ***
ssb rsa2048 2019-03-25 [E] [expires: 2021-03-25]

gpg: DBG: chan_0x00000260 -> HAVEKEY *KEY*
gpg: DBG: chan_0x00000260 <- ERR 67108881 No secret key <GPG Agent>
gpg: DBG: chan_0x00000260 -> HAVEKEY *KEY*
gpg: DBG: chan_0x00000260 <- ERR 67108881 No secret key <GPG Agent>
gpg: DBG: chan_0x00000260 -> HAVEKEY *KEY*
gpg: DBG: chan_0x00000260 <- ERR 67108881 No secret key <GPG Agent>
gpg: secmem usage: 0/32768 bytes in 0 blocks

Is there anything more I can do, replicated it on 3 different machines