diff --git a/gnupg/.gnupg/gpg-agent.conf b/gnupg/.gnupg/gpg-agent.conf
index 390db16..1e5446d 100644
Binary files a/gnupg/.gnupg/gpg-agent.conf and b/gnupg/.gnupg/gpg-agent.conf differ
diff --git a/gnupg/.gnupg/gpg.conf b/gnupg/.gnupg/gpg.conf
new file mode 100644
index 0000000..c59138f
Binary files /dev/null and b/gnupg/.gnupg/gpg.conf differ
diff --git a/gnupg/.gnupg/sshcontrol b/gnupg/.gnupg/sshcontrol
index 397a7b8..aaac24e 100644
Binary files a/gnupg/.gnupg/sshcontrol and b/gnupg/.gnupg/sshcontrol differ
diff --git a/local-bin/.local/bin/pinentry-wrapper b/local-bin/.local/bin/pinentry-wrapper
new file mode 100755
index 0000000..d31df4b
--- /dev/null
+++ b/local-bin/.local/bin/pinentry-wrapper
@@ -0,0 +1,12 @@
+#!/bin/sh
+# Context-aware pinentry wrapper
+# Uses pinentry-curses for terminal sessions and pinentry-gtk for GUI sessions
+
+# Check if we're in a graphical environment
+if [ -n "$DISPLAY" ] || [ -n "$WAYLAND_DISPLAY" ]; then
+    # GUI environment - use GTK pinentry
+    exec /usr/bin/pinentry-gtk "$@"
+else
+    # Terminal environment - use curses pinentry
+    exec /usr/bin/pinentry-curses "$@"
+fi
diff --git a/zsh/.config/zsh/.zprofile b/zsh/.config/zsh/.zprofile
index 89c53d9..6cfc0cc 100644
--- a/zsh/.config/zsh/.zprofile
+++ b/zsh/.config/zsh/.zprofile
@@ -1,6 +1,9 @@
 # === Zsh Profile Configuration ===
 # This file is sourced for login shells
 
+# Source environment configuration (includes GPG setup)
+source ~/.config/env
+
 # Set ZDOTDIR if not already set
 export ZDOTDIR=${ZDOTDIR:-~/.config/zsh}
 
diff --git a/zsh/.config/zsh/zsh_history_fw b/zsh/.config/zsh/zsh_history_fw
index a70fbf6..a49ba33 100644
Binary files a/zsh/.config/zsh/zsh_history_fw and b/zsh/.config/zsh/zsh_history_fw differ