diff --git a/lib/hal/HalGPIO.cpp b/lib/hal/HalGPIO.cpp
index 803efba0..89ce13ba 100644
--- a/lib/hal/HalGPIO.cpp
+++ b/lib/hal/HalGPIO.cpp
@@ -24,12 +24,13 @@ bool HalGPIO::wasAnyReleased() const { return inputMgr.wasAnyReleased(); }
 unsigned long HalGPIO::getHeldTime() const { return inputMgr.getHeldTime(); }
 
 void HalGPIO::startDeepSleep() {
-  esp_deep_sleep_enable_gpio_wakeup(1ULL << InputManager::POWER_BUTTON_PIN, ESP_GPIO_WAKEUP_GPIO_LOW);
   // Ensure that the power button has been released to avoid immediately turning back on if you're holding it
   while (inputMgr.isPressed(BTN_POWER)) {
     delay(50);
     inputMgr.update();
   }
+  // Arm the wakeup trigger *after* the button is released
+  esp_deep_sleep_enable_gpio_wakeup(1ULL << InputManager::POWER_BUTTON_PIN, ESP_GPIO_WAKEUP_GPIO_LOW);
   // Enter Deep Sleep
   esp_deep_sleep_start();
 }
@@ -44,12 +45,20 @@ bool HalGPIO::isUsbConnected() const {
   return digitalRead(UART0_RXD) == HIGH;
 }
 
-bool HalGPIO::isWakeupByPowerButton() const {
+HalGPIO::WakeupReason HalGPIO::getWakeupReason() const {
+  const bool usbConnected = isUsbConnected();
   const auto wakeupCause = esp_sleep_get_wakeup_cause();
   const auto resetReason = esp_reset_reason();
-  if (isUsbConnected()) {
-    return wakeupCause == ESP_SLEEP_WAKEUP_GPIO;
-  } else {
-    return (wakeupCause == ESP_SLEEP_WAKEUP_UNDEFINED) && (resetReason == ESP_RST_POWERON);
+
+  if ((wakeupCause == ESP_SLEEP_WAKEUP_UNDEFINED && resetReason == ESP_RST_POWERON && !usbConnected) ||
+      (wakeupCause == ESP_SLEEP_WAKEUP_GPIO && resetReason == ESP_RST_DEEPSLEEP && usbConnected)) {
+    return WakeupReason::PowerButton;
   }
-}
+  if (wakeupCause == ESP_SLEEP_WAKEUP_UNDEFINED && resetReason == ESP_RST_UNKNOWN && usbConnected) {
+    return WakeupReason::AfterFlash;
+  }
+  if (wakeupCause == ESP_SLEEP_WAKEUP_UNDEFINED && resetReason == ESP_RST_POWERON && usbConnected) {
+    return WakeupReason::AfterUSBPower;
+  }
+  return WakeupReason::Other;
+}
\ No newline at end of file
diff --git a/lib/hal/HalGPIO.h b/lib/hal/HalGPIO.h
index 11ffb22e..615a8d63 100644
--- a/lib/hal/HalGPIO.h
+++ b/lib/hal/HalGPIO.h
@@ -47,8 +47,9 @@ class HalGPIO {
   // Check if USB is connected
   bool isUsbConnected() const;
 
-  // Check if wakeup was caused by power button press
-  bool isWakeupByPowerButton() const;
+  enum class WakeupReason { PowerButton, AfterFlash, AfterUSBPower, Other };
+
+  WakeupReason getWakeupReason() const;
 
   // Button indices
   static constexpr uint8_t BTN_BACK = 0;
diff --git a/src/main.cpp b/src/main.cpp
index df54fb6d..89c4e13c 100644
--- a/src/main.cpp
+++ b/src/main.cpp
@@ -294,10 +294,22 @@ void setup() {
   SETTINGS.loadFromFile();
   KOREADER_STORE.loadFromFile();
 
-  if (gpio.isWakeupByPowerButton()) {
-    // For normal wakeups, verify power button press duration
-    Serial.printf("[%lu] [   ] Verifying power button press duration\n", millis());
-    verifyPowerButtonDuration();
+  switch (gpio.getWakeupReason()) {
+    case HalGPIO::WakeupReason::PowerButton:
+      // For normal wakeups, verify power button press duration
+      Serial.printf("[%lu] [   ] Verifying power button press duration\n", millis());
+      verifyPowerButtonDuration();
+      break;
+    case HalGPIO::WakeupReason::AfterUSBPower:
+      // If USB power caused a cold boot, go back to sleep
+      Serial.printf("[%lu] [   ] Wakeup reason: After USB Power\n", millis());
+      gpio.startDeepSleep();
+      break;
+    case HalGPIO::WakeupReason::AfterFlash:
+      // After flashing, just proceed to boot
+    case HalGPIO::WakeupReason::Other:
+    default:
+      break;
   }
 
   // First serial output only here to avoid timing inconsistencies for power button press duration verification