diff --git a/home/.chezmoiscripts/universal/run_before_02-decrypt-age-key.sh.tmpl b/home/.chezmoiscripts/universal/run_before_02-decrypt-age-key.sh.tmpl
index 7039b5ac..ec6c2e77 100644
--- a/home/.chezmoiscripts/universal/run_before_02-decrypt-age-key.sh.tmpl
+++ b/home/.chezmoiscripts/universal/run_before_02-decrypt-age-key.sh.tmpl
@@ -15,6 +15,10 @@
 #     If you want to automate a headless install that requires access to `encrypted_` files and encrypted variables, then
 #     you can save the decrypted Age key to `~/.config/age/chezmoi.txt` prior to running `bash <(curl -sSL https://install.doctor/start)`.
 #
+#     Alternatively, you can pass in your Age decryption passphrase in using the `AGE_PASSWORD` environment variable.
+#     Install Doctor will use this variable along with expect to headlessly automate the password prompt during the
+#     decryption process.
+#
 #     ## GPG
 #
 #     It is also possible to configure Chezmoi to utilize GPG instead of Age. This might be beneficial if you want to
@@ -28,35 +32,77 @@
 {{ includeTemplate "universal/logg-before" }}
 {{ includeTemplate "universal/profile-before" }}
 
-### Only run decryption process if HEADLESS_INSTALL variable is not set
-if [ -z "$HEADLESS_INSTALL" ]; then
-  ### Install Age via Homebrew if not present
-  if ! command -v age > /dev/null; then
-    if command -v brew > /dev/null; then
-      logg info 'Running `brew install age`'
-      brew install age
-    else
-      logg warn '`age` is not installed which is utilized in the decryption process'
-    fi
-  fi
+### Handle decryption failure
+decryptionFailure() {
+  logg info 'Proceeding without decrypting age encryption key stored at `~/.local/share/chezmoi/home/key.txt.age`'
+  logg info 'To have Chezmoi handle your encryption (so you can store your private files publicly) take a look at https://shorturl.at/jkpzG'
+  logg info 'Removing all files that begin with encrypted_ because decryption failed'
+  find "$HOME/.local/share/chezmoi" -type f -name "encrypted_*" | while read ENCRYPTED_FILE; do
+    logg info "Removing $ENCRYPTED_FILE"
+    rm -f "$ENCRYPTED_FILE"
+  done
+}
 
-  ### Decrypt private key if it is not already present
+### Install Age via Homebrew if not present
+installAge() {
+  if command -v brew > /dev/null; then
+    logg info 'Running `brew install age`'
+    brew install age
+  else
+    logg warn '`age` is not installed which is utilized in the decryption process'
+  fi
+}
+
+### Install Expect via Homebrew if not present
+installExpect() {
+  if command -v brew > /dev/null; then
+    logg info 'Running `brew install expect`'
+    brew install expect
+  else
+    logg warn '`expect` is not installed which is utilized in the decryption process'
+  fi
+}
+
+### Decrypt private key if it is not already present
+decryptKey() {
   if command -v age > /dev/null; then
     if [ ! -f "${XDG_CONFIG_HOME}/age/chezmoi.txt" ]; then
       mkdir -p "${XDG_CONFIG_HOME}/age"
-      logg star '`PRESS ENTER` if you have not set up your encryption token yet'
-      age --decrypt --output "${XDG_CONFIG_HOME}/age/chezmoi.txt" "{{ .chezmoi.sourceDir }}/key.txt.age" || EXIT_CODE=$?
-      if [ -n "$EXIT_CODE" ]; then
-        logg info 'Proceeding without decrypting age encryption key stored at `~/.local/share/chezmoi/home/key.txt.age`'
-        logg info 'To have Chezmoi handle your encryption (so you can store your private files publicly) take a look at https://shorturl.at/jkpzG'
-        logg info 'Removing all files that begin with encrypted_ because decryption failed'
-        find "$HOME/.local/share/chezmoi" -type f -name "encrypted_*" | while read ENCRYPTED_FILE; do
-          logg info "Removing $ENCRYPTED_FILE"
-          rm -f "$ENCRYPTED_FILE"
-        done
+      if [ -z "$AGE_PASSWORD" ]; then
+        logg star '`PRESS ENTER` if you have not set up your encryption token yet'
+        age --decrypt --output "${XDG_CONFIG_HOME}/age/chezmoi.txt" "{{ .chezmoi.sourceDir }}/key.txt.age" || EXIT_CODE=$?
+        if [ -n "$EXIT_CODE" ]; then
+          decryptionFailure
+        else
+          logg success 'The encryption key was successfully decrypted'
+        fi
+      else
+        installExpect
+        expect -c "set timeout -1
+        spawn age --decrypt --output "${XDG_CONFIG_HOME}/age/chezmoi.txt" "/usr/local/src/install.doctor/home/key.txt.age"
+        expect \"Enter passphrase:\"
+        send \"${AGE_PASSWORD}\r\"
+        expect eof" > /dev/null || EXIT_CODE=$?
+        if [ -n "$EXIT_CODE" ]; then
+          logg info 'There was an issue decrypting the `key.txt.age` file with the provided `AGE_PASSWORD`'
+          decryptionFailure
+        else
+          logg info 'The encryption key was successfully decrypted using expect and the provided `AGE_PASSWORD`'
+        fi
       fi
     fi
   fi
+}
+
+### Only run decryption process if HEADLESS_INSTALL variable is not set
+if [ -z "$HEADLESS_INSTALL" ]; then
+  installAge
+  decryptKey
+elif [ -n "$HEADLESS_INSTALL" ] && [ -n "$AGE_PASSWORD" ]; then
+  installAge
+  decryptKey
+else
+  logg info 'Skipping Age key decryption process'
 fi
 
 ### Ensure proper permissions on private key
diff --git a/home/dot_config/Code/User/README.md b/home/dot_config/Code/User/README.md
index 27bcc676..84301420 100644
--- a/home/dot_config/Code/User/README.md
+++ b/home/dot_config/Code/User/README.md
@@ -14,4 +14,6 @@
     // "sonarsource.sonarlint-vscode", Creates a ~/.sonarlint folder. Does not respect XDG spec.
         // "sprkldev.sprkl-vscode", Creates a ~/.sprkl folder. Does not respect XDG spec.
 // Creates ~/.console-ninja folder -- needs to respect XDG
-    // "wallabyjs.console-ninja",
\ No newline at end of file
+    // "wallabyjs.console-ninja",
+    "gitpod.gitpod-remote-ssh", // Bunch of errors like this during install [gitpod-remote-ssh]: Couldn't find message for key openPreview.
+    // "leonardssh.vscord", Discord presence plugin (requires embedding key in settings.json)
\ No newline at end of file
diff --git a/home/dot_config/Code/User/extensions.json b/home/dot_config/Code/User/extensions.json
index 2540604c..eacf712a 100644
--- a/home/dot_config/Code/User/extensions.json
+++ b/home/dot_config/Code/User/extensions.json
@@ -78,7 +78,6 @@
     "github.vscode-pull-request-github",
     "gitlab.gitlab-workflow",
     "gitpod.gitpod-desktop",
-    "gitpod.gitpod-remote-ssh",
     "golang.go",
     "google-home.google-home-extension",
     "googlecloudtools.cloudcode",
@@ -115,9 +114,7 @@
     "kruemelkatze.vscode-dashboard",
     "l13rary.l13-diff",
     "lennartlence.chadcommit",
-    "leonardssh.vscord",
     "llvm-vs-code-extensions.vscode-clangd",
-    "logerfo.gitlab-notifications",
     "lottiefiles.vscode-lottie",
     "loyieking.smalise",
     "mads-hartmann.bash-ide-vscode",
diff --git a/home/dot_config/shell/private_private.sh.tmpl b/home/dot_config/shell/private_private.sh.tmpl
index 7229c9f8..bd5cc76d 100644
--- a/home/dot_config/shell/private_private.sh.tmpl
+++ b/home/dot_config/shell/private_private.sh.tmpl
@@ -35,6 +35,21 @@ export GITLAB_TOKEN="$GL_TOKEN"
 ### Heroku
 export HEROKU_API_KEY="{{ if (stat (joinPath .chezmoi.sourceDir ".chezmoitemplates" "secrets" "HEROKU_API_KEY")) }}{{ includeTemplate "secrets/HEROKU_API_KEY" | decrypt }}{{ else }}{{ env "HEROKU_API_KEY" }}{{ end }}"
 
+### Install Doctor
+export HEADLESS_INSTALL=true
+export SOFTWARE_GROUP="Full"
+export FULL_NAME="Brian Zalewski"
+export PRIMARY_EMAIL="help@megabyte.space"
+export PUBLIC_SERVICES_DOMAIN="megabyte.space"
+export RESTRICTED_ENVIRONMENT=false
+export WORK_ENVIRONMENT=false
+export HOST="$HOST"
+
+# Set to work environment if Cisco applications are installed (modify this to your liking)
+if [ -d /Applications/Cisco ]; then
+    export WORK_ENVIRONMENT=true
+fi
+
 ### Megabyte Labs
 export FULLY_AUTOMATED_TASKS=true