diff --git a/README.md b/README.md
index 86108ca7a..806f71332 100644
--- a/README.md
+++ b/README.md
@@ -303,12 +303,12 @@ This script automatically:
   - **`Cmd+Shift+V`** - Voice edit clipboard text
 
 > [!NOTE]
-> After setup, you may need to grant Accessibility permissions to skhd in System Settings → Privacy & Security → Accessibility
+> After setup, you may need to grant Accessibility permissions to skhd in System Settings → Privacy & Security → Accessibility. The transcription hotkey may also prompt for Microphone access for skhd the first time it records.
 
 > [!TIP]
 > To keep the recording-status notification visible for the whole flow, open System Settings → Notifications → *terminal-notifier* and set the Alert style to **Persistent** (or choose **Alerts** on older macOS versions).
 > Also enable "Allow notification when mirroring or sharing the display".
-> The hotkey scripts keep only the recording notification pinned; status and result toasts auto-dismiss.
+> The hotkey scripts keep only the recording notification pinned; status and result toasts auto-dismiss. Transcription hotkey diagnostics are written to `~/.cache/agent-cli/transcribe-hotkey.log` and `~/.cache/agent-cli/transcribe-hotkey-agent.log`.
 
 ### Linux Hotkeys
 
diff --git a/agent_cli/install/hotkeys.py b/agent_cli/install/hotkeys.py
index bb8c24f76..8f1edef6e 100644
--- a/agent_cli/install/hotkeys.py
+++ b/agent_cli/install/hotkeys.py
@@ -33,6 +33,7 @@ def install_hotkeys() -> None:
     2. Creates config at `~/.config/skhd/skhdrc`
     3. Starts skhd as a background service
     4. May require Accessibility permissions: System Settings → Privacy & Security → Accessibility → enable 'skhd'
+    5. May require Microphone permissions when the transcription hotkey first records
 
     **Linux** (manual DE configuration):
 
@@ -76,3 +77,7 @@ def install_hotkeys() -> None:
             "cyan",
         )
         print_with_style("  2. Add and enable 'skhd'", "cyan")
+        print_with_style(
+            "  3. Allow Microphone access for 'skhd' when prompted by the transcription hotkey",
+            "cyan",
+        )
diff --git a/docs/commands/install-hotkeys.md b/docs/commands/install-hotkeys.md
index 9d8ff8c03..0ca94b09c 100644
--- a/docs/commands/install-hotkeys.md
+++ b/docs/commands/install-hotkeys.md
@@ -32,7 +32,7 @@ Sets up hotkeys for common workflows:
 - Super+Shift+A: Autocorrect clipboard text
 - Super+Shift+V: Voice edit clipboard text
 
-On macOS, you may need to grant Accessibility permissions to skhd in System Settings → Privacy & Security → Accessibility.
+On macOS, you may need to grant Accessibility permissions to skhd in System Settings → Privacy & Security → Accessibility. The transcription hotkey may also prompt for Microphone access for skhd the first time it records.
 
 On a fresh install, `agent-cli install-hotkeys` may take longer than expected because it can download Python extras before setting up the platform-specific scripts.
 
diff --git a/docs/system-integration.md b/docs/system-integration.md
index bcb0c0f39..fe8defc91 100644
--- a/docs/system-integration.md
+++ b/docs/system-integration.md
@@ -36,6 +36,10 @@ This automatically installs missing `audio` and `llm` extras, then sets up the p
 >
 > After installation, grant Accessibility permissions to skhd:
 > System Settings → Privacy & Security → Accessibility → enable "skhd"
+>
+> The transcription hotkey may also prompt for Microphone permission for "skhd"
+> the first time it starts recording. Allow it so hotkey-launched recordings
+> contain real audio instead of silence.
 
 ### Manual skhd Configuration
 
@@ -67,6 +71,9 @@ skhd --reload
 
 The `install-hotkeys` command automatically installs terminal-notifier for visual feedback and keeps the active recording-status notification pinned while transient status/result toasts auto-dismiss.
 
+Transcription hotkey diagnostics are written to `~/.cache/agent-cli/transcribe-hotkey.log`
+and `~/.cache/agent-cli/transcribe-hotkey-agent.log`.
+
 Configure notifications in System Settings:
 1. Settings → Notifications → terminal-notifier
 2. Enable "Allow Notifications"
diff --git a/scripts/macos-hotkeys/README.md b/scripts/macos-hotkeys/README.md
index 9b12a31f9..e0e9afbc0 100644
--- a/scripts/macos-hotkeys/README.md
+++ b/scripts/macos-hotkeys/README.md
@@ -15,6 +15,8 @@ System-wide hotkeys for agent-cli voice AI features on macOS.
 - **`Cmd+Shift+V`** → Toggle voice edit mode for clipboard
 
 Results appear in notifications and clipboard.
+Diagnostics are written to `~/.cache/agent-cli/transcribe-hotkey.log` and
+`~/.cache/agent-cli/transcribe-hotkey-agent.log`.
 
 > [!TIP]
 > For a persistent recording-status notification, open System Settings → Notifications → *terminal-notifier* and set the Alert style to **Persistent** (or choose **Alerts** on older macOS versions).
@@ -32,6 +34,9 @@ Results appear in notifications and clipboard.
 **Hotkey not working?**
 - Grant accessibility permissions in System Settings
 
+**Recording is silent?**
+- Allow microphone permissions for `skhd` in System Settings
+
 **No notifications?**
 ```bash
 terminal-notifier -title "Test" -message "Hello"
diff --git a/scripts/macos-hotkeys/toggle-transcription.sh b/scripts/macos-hotkeys/toggle-transcription.sh
index 53738c191..06bd03f0d 100755
--- a/scripts/macos-hotkeys/toggle-transcription.sh
+++ b/scripts/macos-hotkeys/toggle-transcription.sh
@@ -4,17 +4,27 @@
 
 NOTIFIER=${NOTIFIER:-/opt/homebrew/bin/terminal-notifier}
 AGENT_CLI=${AGENT_CLI:-"$HOME/.local/bin/agent-cli"}
-PID_FILE=${PID_FILE:-"$HOME/.cache/agent-cli/transcribe.pid"}
+CACHE_DIR=${CACHE_DIR:-"$HOME/.cache/agent-cli"}
+LAST_FILE=${LAST_FILE:-"$CACHE_DIR/transcribe-hotkey.last"}
+LOG_FILE=${LOG_FILE:-"$CACHE_DIR/transcribe-hotkey.log"}
+AGENT_LOG_FILE=${AGENT_LOG_FILE:-"$CACHE_DIR/transcribe-hotkey-agent.log"}
+DEBOUNCE_SECONDS=${DEBOUNCE_SECONDS:-1}
 RECORDING_GROUP="agent-cli-transcribe-recording"
 TEMP_PREFIX="agent-cli-transcribe-temp"
 
+mkdir -p "$CACHE_DIR"
+
+log_event() {
+    printf '%s %s\n' "$(date '+%Y-%m-%dT%H:%M:%S%z')" "$*" >> "$LOG_FILE"
+}
+
 notify_temp() {
     local title=$1
     local message=$2
     local duration=${3:-4}  # 4 seconds default
     local group="${TEMP_PREFIX}-${RANDOM}-$$"
 
-    "$NOTIFIER" -title "$title" -message "$message" -group "$group"
+    "$NOTIFIER" -title "$title" -message "$message" -group "$group" || true
     (
         sleep "$duration"
         "$NOTIFIER" -remove "$group" >/dev/null 2>&1 || true
@@ -22,26 +32,48 @@ notify_temp() {
 }
 
 is_transcribe_running() {
-    [ -f "$PID_FILE" ] || return 1
-    local pid
-    pid=$(cat "$PID_FILE" 2>/dev/null || true)
-    [ -n "$pid" ] && kill -0 "$pid" >/dev/null 2>&1
+    local status_json
+    if ! status_json=$("$AGENT_CLI" transcribe --status --json 2>> "$LOG_FILE"); then
+        log_event "status check failed"
+        return 1
+    fi
+    log_event "status: $status_json"
+    printf '%s\n' "$status_json" | grep -Eq '"running"[[:space:]]*:[[:space:]]*true'
 }
 
+now=$(date +%s)
+last=$(cat "$LAST_FILE" 2>/dev/null || echo 0)
+
+# skhd can emit repeated key-down events while the hotkey chord is held.
+# Ignore immediate repeats so one press cannot start and stop recording.
+if [ "$((now - last))" -lt "$DEBOUNCE_SECONDS" ]; then
+    log_event "ignored repeat hotkey"
+    exit 0
+fi
+
+echo "$now" > "$LAST_FILE"
+log_event "hotkey pressed"
+
 if is_transcribe_running; then
-    "$AGENT_CLI" transcribe --toggle --quiet >/dev/null 2>&1 || true
+    "$AGENT_CLI" transcribe --stop --quiet --wait-for-start --log-file "$AGENT_LOG_FILE" >> "$LOG_FILE" 2>&1 || true
 
     "$NOTIFIER" -remove "$RECORDING_GROUP" >/dev/null 2>&1 || true
     notify_temp "🛑 Stopped" "Processing results..."
+    log_event "stop requested"
 else
-    "$NOTIFIER" -title "🎙️ Starting" -message "Preparing transcription..." -group "$RECORDING_GROUP"
+    "$NOTIFIER" -title "🎙️ Recording" -message "Press Cmd+Shift+R again to stop." -group "$RECORDING_GROUP" || true
     (
-        OUTPUT=$("$AGENT_CLI" transcribe --toggle --llm --quiet 2>/dev/null)
+        OUTPUT=$("$AGENT_CLI" transcribe --start --llm --quiet --log-file "$AGENT_LOG_FILE" 2>> "$LOG_FILE")
+        status=$?
         "$NOTIFIER" -remove "$RECORDING_GROUP" >/dev/null 2>&1 || true
-        if [ -n "$OUTPUT" ]; then
+        if [ "$status" -ne 0 ]; then
+            notify_temp "❌ Error" "Transcription failed. See $AGENT_LOG_FILE"
+        elif [ -n "$OUTPUT" ]; then
             notify_temp "📄 Result" "$OUTPUT"
         else
-            notify_temp "❌ Error" "No output"
+            notify_temp "⚠️ No Transcript" "Recording captured no speech."
         fi
+        log_event "recording finished with status $status"
     ) &
+    log_event "recording started"
 fi
diff --git a/scripts/setup-macos-hotkeys.sh b/scripts/setup-macos-hotkeys.sh
index 0ad572b7e..f013b3845 100755
--- a/scripts/setup-macos-hotkeys.sh
+++ b/scripts/setup-macos-hotkeys.sh
@@ -20,6 +20,33 @@ fi
 brew install terminal-notifier
 brew tap jackielii/tap && brew install jackielii/tap/skhd-zig
 
+REREGISTER_SKHD_SERVICE=0
+
+patch_skhd_microphone_usage() {
+    local app_path
+    app_path="$(brew --prefix skhd-zig)/skhd.app"
+
+    if [[ ! -d "$app_path" ]]; then
+        return
+    fi
+
+    if /usr/libexec/PlistBuddy -c "Print :NSMicrophoneUsageDescription" "$app_path/Contents/Info.plist" >/dev/null 2>&1; then
+        return
+    fi
+
+    echo "🎙️ Adding microphone usage description to skhd.app..."
+    plutil -insert NSMicrophoneUsageDescription \
+        -string "skhd launches agent-cli voice transcription hotkeys that record from the microphone." \
+        "$app_path/Contents/Info.plist"
+    codesign --force --deep --sign - "$app_path" >/dev/null
+    tccutil reset Microphone com.jackielii.skhd >/dev/null 2>&1 || true
+    tccutil reset Accessibility com.jackielii.skhd >/dev/null 2>&1 || true
+    tccutil reset ListenEvent com.jackielii.skhd >/dev/null 2>&1 || true
+    REREGISTER_SKHD_SERVICE=1
+}
+
+patch_skhd_microphone_usage
+
 # Setup configuration
 echo "⚙️ Setting up configuration..."
 mkdir -p ~/.config/skhd
@@ -38,6 +65,9 @@ EOF
 
 # Start service
 echo "🚀 Starting skhd..."
+if [[ "$REREGISTER_SKHD_SERVICE" = "1" ]]; then
+    skhd --uninstall-service >/dev/null 2>&1 || true
+fi
 skhd --start-service
 
 # Test
@@ -53,6 +83,7 @@ echo ""
 echo "If the hotkey doesn't work:"
 echo "1. Open System Settings → Privacy & Security → Accessibility"
 echo "2. Add and enable 'skhd'"
+echo "3. If prompted, allow Microphone access for 'skhd'"
 echo ""
 echo "If the notification doesn't show:"
 echo "1. Open System Settings → Notifications"
diff --git a/tests/test_macos_hotkeys.py b/tests/test_macos_hotkeys.py
new file mode 100644
index 000000000..ac7354ac0
--- /dev/null
+++ b/tests/test_macos_hotkeys.py
@@ -0,0 +1,120 @@
+"""Tests for macOS hotkey shell script behavior."""
+
+from __future__ import annotations
+
+import os
+import subprocess
+import time
+from pathlib import Path
+
+ROOT = Path(__file__).resolve().parents[1]
+TOGGLE_TRANSCRIPTION = ROOT / "scripts" / "macos-hotkeys" / "toggle-transcription.sh"
+
+
+def _write_executable(path: Path, content: str) -> None:
+    path.write_text(content, encoding="utf-8")
+    path.chmod(0o755)
+
+
+def _run_toggle_script(
+    tmp_path: Path,
+    agent_cli_body: str,
+    *,
+    expected_notifications: int = 2,
+) -> tuple[list[str], list[str]]:
+    bin_dir = tmp_path / "bin"
+    bin_dir.mkdir()
+    command_log = tmp_path / "commands.log"
+    notification_log = tmp_path / "notifications.log"
+
+    _write_executable(
+        bin_dir / "agent-cli",
+        f"""#!/usr/bin/env bash
+set -euo pipefail
+printf '%s\\n' "$*" >> "{command_log}"
+{agent_cli_body}
+""",
+    )
+    _write_executable(
+        bin_dir / "terminal-notifier",
+        f"""#!/usr/bin/env bash
+printf '%s\\n' "$*" >> "{notification_log}"
+""",
+    )
+
+    env = {
+        **os.environ,
+        "AGENT_CLI": str(bin_dir / "agent-cli"),
+        "NOTIFIER": str(bin_dir / "terminal-notifier"),
+        "HOME": str(tmp_path),
+    }
+    subprocess.run([str(TOGGLE_TRANSCRIPTION)], check=True, env=env)
+
+    deadline = time.monotonic() + 2
+    while time.monotonic() < deadline:
+        command_count = (
+            len(command_log.read_text(encoding="utf-8").splitlines()) if command_log.exists() else 0
+        )
+        notification_count = (
+            len(notification_log.read_text(encoding="utf-8").splitlines())
+            if notification_log.exists()
+            else 0
+        )
+        if command_count >= 2 and notification_count >= expected_notifications:
+            break
+        time.sleep(0.01)
+
+    commands = command_log.read_text(encoding="utf-8").splitlines() if command_log.exists() else []
+    notifications = (
+        notification_log.read_text(encoding="utf-8").splitlines()
+        if notification_log.exists()
+        else []
+    )
+    return commands, notifications
+
+
+def test_macos_transcription_hotkey_stops_using_process_status_json(tmp_path: Path) -> None:
+    commands, notifications = _run_toggle_script(
+        tmp_path,
+        """
+if [[ "$*" == "transcribe --status --json" ]]; then
+    printf '{"action":"status","process":"transcribe","running":true,"status":"running","pid":123,"stale_cleaned":false}\\n'
+    exit 0
+fi
+if [[ "$*" == "transcribe --stop --quiet --wait-for-start"* ]]; then
+    exit 0
+fi
+printf 'unexpected command: %s\\n' "$*" >&2
+exit 2
+""",
+    )
+
+    assert commands[0] == "transcribe --status --json"
+    assert commands[1].startswith("transcribe --stop --quiet --wait-for-start")
+    assert not any("--toggle" in command for command in commands)
+    assert any("Stopped" in notification for notification in notifications)
+
+
+def test_macos_transcription_hotkey_starts_from_process_status_json(tmp_path: Path) -> None:
+    commands, notifications = _run_toggle_script(
+        tmp_path,
+        """
+if [[ "$*" == "transcribe --status --json" ]]; then
+    printf '{"action":"status","process":"transcribe","running":false,"status":"stopped","pid":null,"stale_cleaned":false}\\n'
+    exit 0
+fi
+if [[ "$*" == "transcribe --start --llm --quiet"* ]]; then
+    printf 'hello from transcript\\n'
+    exit 0
+fi
+printf 'unexpected command: %s\\n' "$*" >&2
+exit 2
+""",
+        expected_notifications=3,
+    )
+
+    assert commands[0] == "transcribe --status --json"
+    assert commands[1].startswith("transcribe --start --llm --quiet")
+    assert not any("--toggle" in command for command in commands)
+    assert any("Recording" in notification for notification in notifications)
+    assert any("hello from transcript" in notification for notification in notifications)