The prompt dialog starts in background after first run when using a GUI app (like editor/IDEs)

[maicol07]

Description

The prompt dialog starts in the background, behind the GUI application that calls GPG (editor/IDE). It's better if the dialog starts in the foreground

Setup

• Description of your computer hardware
• Windows 11 build 25188.1000
• Version of gpg: 2.2.27
• Version of pinentry-wsl-ps1.sh: dev-master
• Version of the (optional) davotronic5000/PowerShell_Credential_Manager: None
• Describe how you installed pinentry-wsl-ps1.sh on your computer: I've followed the setup section in the README
• Detail any options you changed inside the pinentry-wsl-ps1.sh file: None

Steps to reproduce

Try to sign something with GPG, either from a terminal or IDE (I've tested this with Jetbrains IDEs and Windows Terminal). For example:

• Open WSL in Windows Terminal
• Type echo "test" | gpg --clearsign
• Sign this message with GPG
• Wait the pinentry timeout
• Resign again
• See the password dialog has spawned behind the terminal

Actual Result

The prompt dialog starts in the background

Expected Result

The prompt dialog starts in the foreground, above the window that calls GPG (editor/IDE).

Workarounds

None

GPG-agent log file

2022-09-12 10:01:30 gpg-agent[5263] listening on socket '/home/maicol07/.gnupg/S.gpg-agent'
2022-09-12 10:01:30 gpg-agent[5263] listening on socket '/home/maicol07/.gnupg/S.gpg-agent.extra'
2022-09-12 10:01:30 gpg-agent[5263] listening on socket '/home/maicol07/.gnupg/S.gpg-agent.browser'
2022-09-12 10:01:30 gpg-agent[5263] listening on socket '/home/maicol07/.gnupg/S.gpg-agent.ssh'
2022-09-12 10:01:30 gpg-agent[5264] gpg-agent (GnuPG) 2.2.35 started
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK Pleased to meet you, process 5262
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- RESET
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- OPTION ttytype=xterm-256color
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- OPTION display=:0.0
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- OPTION putenv=WAYLAND_DISPLAY=wayland-0
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- GETINFO version
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> D 2.2.35
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- OPTION allow-pinentry-notify
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- OPTION agent-awareness=2.1.0
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- HAVEKEY <CONFIDENTIAL><CONFIDENTIAL>
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- KEYINFO <CONFIDENTIAL>
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> S KEYINFO <CONFIDENTIAL>D - - - P - - -
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- RESET
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- SIGKEY <CONFIDENTIAL>
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- SETKEYDESC Please+enter+the+passphrase+to+unlock+the+OpenPGP+secret+key:%0A%22<CONFIDENTIAL>%22%0A4096-bit+RSA+key,+ID+<CONFIDENTIAL>,%0Acreated+2021-06-30.%0A
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- SETHASH 10 <CONFIDENTIAL>
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- PKSIGN
2022-09-12 10:01:30 gpg-agent[5264] starting a new PIN Entry
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK Your orders please
2022-09-12 10:01:30 gpg-agent[5264] DBG: connection to PIN entry established
2022-09-12 10:01:30 gpg-agent[5264] DBG: pinentry: atfork used setenv(DISPLAY,:0.0)
2022-09-12 10:01:30 gpg-agent[5264] DBG: pinentry: atfork used setenv(WAYLAND_DISPLAY,wayland-0)
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION no-grab
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION ttytype=xterm-256color
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION allow-external-password-cache
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION default-ok=_OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION default-cancel=_Cancel
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION default-yes=_Yes
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION default-no=_No
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION default-prompt=PIN:
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION default-pwmngr=_Save in password manager
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION default-cf-visi=Do you really want to make your passphrase visible on the screen?
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION default-tt-visi=Make passphrase visible
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION default-tt-hide=Hide passphrase
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION touch-file=/home/maicol07/.gnupg/S.gpg-agent
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> OPTION owner=5262 MAICOL-ROG
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> GETINFO flavor
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- ERR 83886355 unknown command
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> GETINFO version
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- D 0.2.1
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> GETINFO ttyinfo
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- ERR 83886355 unknown command
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> GETINFO pid
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- D 5266
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 -> INQUIRE PINENTRY_LAUNCHED 5266 unknown 0.2.1 ? ? ?
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_10 <- END
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> SETKEYINFO n/<CONFIDENTIAL>
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> SETDESC Please enter the passphrase to unlock the OpenPGP secret key:%0A%22<CONFIDENTIAL>%22%0A4096-bit RSA key, ID <CONFIDENTIAL>,%0Acreated 2021-06-30.%0A
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> SETPROMPT Passphrase:
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:01:30 gpg-agent[5264] DBG: chan_11 -> [[Confidential data not shown]]
2022-09-12 10:01:35 gpg-agent[5264] DBG: chan_11 <- [[Confidential data not shown]]
2022-09-12 10:01:35 gpg-agent[5264] DBG: chan_11 <- [[Confidential data not shown]]
2022-09-12 10:01:35 gpg-agent[5264] DBG: chan_11 -> BYE
2022-09-12 10:01:35 gpg-agent[5264] DBG: chan_10 -> [ 44 20 28 37 3a 73 69 67 2d 76 61 6c 28 33 3a 72 ...(535 byte(s) skipped) ]
2022-09-12 10:01:35 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:01:35 gpg-agent[5264] DBG: chan_10 <- [eof]
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK Pleased to meet you, process 6762
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- RESET
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- OPTION ttytype=xterm-256color
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- OPTION display=:0.0
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- OPTION putenv=WAYLAND_DISPLAY=wayland-0
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- GETINFO version
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> D 2.2.35
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- OPTION allow-pinentry-notify
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- OPTION agent-awareness=2.1.0
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- HAVEKEY <CONFIDENTIAL><CONFIDENTIAL>
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- KEYINFO <CONFIDENTIAL>
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> S KEYINFO <CONFIDENTIAL> D - - 1 P - - -
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- RESET
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- SIGKEY <CONFIDENTIAL>
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- SETKEYDESC Please+enter+the+passphrase+to+unlock+the+OpenPGP+secret+key:%0A%22<CONFIDENTIAL>%22%0A4096-bit+RSA+key,+ID+4FDB0F87CDB1D34A,%0Acreated+2021-06-30.%0A
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- SETHASH 10 <CONFIDENTIAL>
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- PKSIGN
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> [ 44 20 28 37 3a 73 69 67 2d 76 61 6c 28 33 3a 72 ...(533 byte(s) skipped) ]
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:09:38 gpg-agent[5264] DBG: chan_10 <- [eof]
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK Pleased to meet you, process 9930
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- RESET
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- OPTION ttytype=xterm-256color
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- OPTION display=:0.0
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- OPTION putenv=WAYLAND_DISPLAY=wayland-0
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- GETINFO version
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> D 2.2.35
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- OPTION allow-pinentry-notify
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- OPTION agent-awareness=2.1.0
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- HAVEKEY <CONFIDENTIAL><CONFIDENTIAL>
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- KEYINFO <CONFIDENTIAL>
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> S KEYINFO <CONFIDENTIAL>D - - - P - - -
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- RESET
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- SIGKEY <CONFIDENTIAL>
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- SETKEYDESC Please+enter+the+passphrase+to+unlock+the+OpenPGP+secret+key:%0A%22<CONFIDENTIAL>%22%0A4096-bit+RSA+key,+ID+<CONFIDENTIAL>,%0Acreated+2021-06-30.%0A
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- SETHASH 10 <CONFIDENTIAL>
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- PKSIGN
2022-09-12 10:23:25 gpg-agent[5264] starting a new PIN Entry
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK Your orders please
2022-09-12 10:23:25 gpg-agent[5264] DBG: connection to PIN entry established
2022-09-12 10:23:25 gpg-agent[5264] DBG: pinentry: atfork used setenv(DISPLAY,:0.0)
2022-09-12 10:23:25 gpg-agent[5264] DBG: pinentry: atfork used setenv(WAYLAND_DISPLAY,wayland-0)
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION no-grab
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION ttytype=xterm-256color
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION allow-external-password-cache
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION default-ok=_OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION default-cancel=_Cancel
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION default-yes=_Yes
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION default-no=_No
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION default-prompt=PIN:
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION default-pwmngr=_Save in password manager
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION default-cf-visi=Do you really want to make your passphrase visible on the screen?
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION default-tt-visi=Make passphrase visible
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION default-tt-hide=Hide passphrase
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION touch-file=/home/maicol07/.gnupg/S.gpg-agent
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> OPTION owner=9930 MAICOL-ROG
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> GETINFO flavor
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- ERR 83886355 unknown command
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> GETINFO version
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- D 0.2.1
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> GETINFO ttyinfo
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- ERR 83886355 unknown command
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> GETINFO pid
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- D 9932
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 -> INQUIRE PINENTRY_LAUNCHED 9932 unknown 0.2.1 ? ? ?
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_10 <- END
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> SETKEYINFO n/<CONFIDENTIAL>
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> SETDESC Please enter the passphrase to unlock the OpenPGP secret key:%0A%22<CONFIDENTIAL>%22%0A4096-bit RSA key, ID <CONFIDENTIAL>,%0Acreated 2021-06-30.%0A
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> SETPROMPT Passphrase:
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 <- OK
2022-09-12 10:23:25 gpg-agent[5264] DBG: chan_11 -> [[Confidential data not shown]]
2022-09-12 10:23:40 gpg-agent[5264] DBG: chan_11 <- [[Confidential data not shown]]
2022-09-12 10:23:40 gpg-agent[5264] DBG: chan_11 <- [[Confidential data not shown]]
2022-09-12 10:23:41 gpg-agent[5264] DBG: chan_11 -> BYE
2022-09-12 10:23:41 gpg-agent[5264] DBG: chan_10 -> [ 44 20 28 37 3a 73 69 67 2d 76 61 6c 28 33 3a 72 ...(531 byte(s) skipped) ]
2022-09-12 10:23:41 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:23:41 gpg-agent[5264] DBG: chan_10 <- [eof]
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK Pleased to meet you, process 11738
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- RESET
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- OPTION ttytype=xterm-256color
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- OPTION display=:0.0
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- OPTION putenv=WAYLAND_DISPLAY=wayland-0
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- GETINFO version
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> D 2.2.35
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- OPTION allow-pinentry-notify
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- OPTION agent-awareness=2.1.0
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- HAVEKEY <CONFIDENTIAL><CONFIDENTIAL>
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- KEYINFO <CONFIDENTIAL>
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> S KEYINFO <CONFIDENTIAL> D - - 1 P - - -
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- RESET
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- SIGKEY <CONFIDENTIAL>
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- SETKEYDESC Please+enter+the+passphrase+to+unlock+the+OpenPGP+secret+key:%0A%22<CONFIDENTIAL>%22%0A4096-bit+RSA+key,+ID+<CONFIDENTIAL>,%0Acreated+2021-06-30.%0A
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- SETHASH 10 <CONFIDENTIAL>
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:02 gpg-agent[5264] DBG: chan_10 <- PKSIGN
2022-09-12 10:24:03 gpg-agent[5264] DBG: chan_10 -> [ 44 20 28 37 3a 73 69 67 2d 76 61 6c 28 33 3a 72 ...(531 byte(s) skipped) ]
2022-09-12 10:24:03 gpg-agent[5264] DBG: chan_10 -> OK
2022-09-12 10:24:03 gpg-agent[5264] DBG: chan_10 <- [eof]

[diablodale]

I can't repro your issue.

Also, I do not understand step 4 "Wait the pinentry timeout". There is no timeout. The dialog box asking for the password will infinitely wait. I waited 5 minutes and then pressed cancel.

[SimonMaths]

I believe what "Wait the pinentry timeout" means to wait so that the gpg-agent no longer has the passphrase cached, this can be skipped by setting ttl to 0 in the gpg-agent settings for example.

I had a similar issue with the dialog appearing in the background from the second time it appears onward, but this seems to have be resolved with an update to Windows 11. [edit: ] I was wrong, the problem still sometimes occurs in Windows 11, though I can't seem to make it happen reliably.