diff --git a/wled00/ota_update.cpp b/wled00/ota_update.cpp
index 042a14f9..bffaa511 100644
--- a/wled00/ota_update.cpp
+++ b/wled00/ota_update.cpp
@@ -7,6 +7,11 @@
 #include <esp_flash.h>
 #endif
 
+// Forward declarations
+#if defined(ARDUINO_ARCH_ESP32) && !defined(WLED_DISABLE_OTA)
+void invalidateBootloaderSHA256Cache();
+#endif
+
 // Platform-specific metadata locations
 #ifdef ESP32
 constexpr size_t METADATA_OFFSET = 256;          // ESP32: metadata appears after Espressif metadata
@@ -390,4 +395,182 @@ bool verifyBootloaderImage(const uint8_t* buffer, size_t len, String* bootloader
 
   return true;
 }
+
+// Bootloader OTA context structure
+struct BootloaderUpdateContext {
+  // State flags
+  bool replySent = false;
+  bool uploadComplete = false;
+  String errorMessage;
+
+  // Buffer to hold bootloader data
+  uint8_t* buffer = nullptr;
+  size_t bytesBuffered = 0;
+  const uint32_t bootloaderOffset = 0x1000;
+  const uint32_t maxBootloaderSize = 0x10000; // 64KB buffer size
+};
+
+// Cleanup bootloader OTA context
+static void endBootloaderOTA(AsyncWebServerRequest *request) {
+  BootloaderUpdateContext* context = reinterpret_cast<BootloaderUpdateContext*>(request->_tempObject);
+  request->_tempObject = nullptr;
+
+  DEBUG_PRINTF_P(PSTR("EndBootloaderOTA %x --> %x\n"), (uintptr_t)request, (uintptr_t)context);
+  if (context) {
+    if (context->buffer) {
+      free(context->buffer);
+      context->buffer = nullptr;
+    }
+
+    // If update failed, restore system state
+    if (!context->uploadComplete || !context->errorMessage.isEmpty()) {
+      strip.resume();
+      #if WLED_WATCHDOG_TIMEOUT > 0
+      WLED::instance().enableWatchdog();
+      #endif
+    }
+
+    delete context;
+  }
+}
+
+// Initialize bootloader OTA context
+bool initBootloaderOTA(AsyncWebServerRequest *request) {
+  if (request->_tempObject) {
+    return true; // Already initialized
+  }
+
+  BootloaderUpdateContext* context = new BootloaderUpdateContext();
+  if (!context) {
+    DEBUG_PRINTLN(F("Failed to allocate bootloader OTA context"));
+    return false;
+  }
+
+  request->_tempObject = context;
+  request->onDisconnect([=]() { endBootloaderOTA(request); });  // ensures cleanup on disconnect
+
+  DEBUG_PRINTLN(F("Bootloader Update Start - initializing buffer"));
+  #if WLED_WATCHDOG_TIMEOUT > 0
+  WLED::instance().disableWatchdog();
+  #endif
+  lastEditTime = millis(); // make sure PIN does not lock during update
+  strip.suspend();
+  strip.resetSegments();
+
+  // Check available heap before attempting allocation
+  size_t freeHeap = getFreeHeapSize();
+  DEBUG_PRINTF_P(PSTR("Free heap before bootloader buffer allocation: %d bytes (need %d bytes)\n"), freeHeap, context->maxBootloaderSize);
+
+  context->buffer = (uint8_t*)malloc(context->maxBootloaderSize);
+  if (!context->buffer) {
+    size_t freeHeapNow = getFreeHeapSize();
+    DEBUG_PRINTF_P(PSTR("Failed to allocate %d byte bootloader buffer! Free heap: %d bytes\n"), context->maxBootloaderSize, freeHeapNow);
+    context->errorMessage = "Out of memory! Free heap: " + String(freeHeapNow) + " bytes, need: " + String(context->maxBootloaderSize) + " bytes";
+    strip.resume();
+    #if WLED_WATCHDOG_TIMEOUT > 0
+    WLED::instance().enableWatchdog();
+    #endif
+    return false;
+  }
+
+  context->bytesBuffered = 0;
+  return true;
+}
+
+// Set bootloader OTA replied flag
+void setBootloaderOTAReplied(AsyncWebServerRequest *request) {
+  BootloaderUpdateContext* context = reinterpret_cast<BootloaderUpdateContext*>(request->_tempObject);
+  if (context) {
+    context->replySent = true;
+  }
+}
+
+// Get bootloader OTA result
+std::pair<bool, String> getBootloaderOTAResult(AsyncWebServerRequest *request) {
+  BootloaderUpdateContext* context = reinterpret_cast<BootloaderUpdateContext*>(request->_tempObject);
+
+  if (!context) {
+    return std::make_pair(true, String(F("Internal error: No bootloader OTA context")));
+  }
+
+  bool needsReply = !context->replySent;
+  String errorMsg = context->errorMessage;
+
+  // If upload was successful, return empty string and trigger reboot
+  if (context->uploadComplete && errorMsg.isEmpty()) {
+    doReboot = true;
+    endBootloaderOTA(request);
+    return std::make_pair(needsReply, String());
+  }
+
+  // If there was an error, return it
+  if (!errorMsg.isEmpty()) {
+    endBootloaderOTA(request);
+    return std::make_pair(needsReply, errorMsg);
+  }
+
+  // Should never happen
+  return std::make_pair(true, String(F("Internal software failure")));
+}
+
+// Handle bootloader OTA data
+void handleBootloaderOTAData(AsyncWebServerRequest *request, size_t index, uint8_t *data, size_t len, bool isFinal) {
+  BootloaderUpdateContext* context = reinterpret_cast<BootloaderUpdateContext*>(request->_tempObject);
+
+  if (!context) {
+    DEBUG_PRINTLN(F("No bootloader OTA context - ignoring data"));
+    return;
+  }
+
+  // Buffer the incoming data
+  if (context->buffer && context->bytesBuffered + len <= context->maxBootloaderSize) {
+    memcpy(context->buffer + context->bytesBuffered, data, len);
+    context->bytesBuffered += len;
+    DEBUG_PRINTF_P(PSTR("Bootloader buffer progress: %d / %d bytes\n"), context->bytesBuffered, context->maxBootloaderSize);
+  } else if (!context->buffer) {
+    DEBUG_PRINTLN(F("Bootloader buffer not allocated!"));
+    context->errorMessage = "Internal error: Bootloader buffer not allocated";
+    return;
+  } else {
+    size_t totalSize = context->bytesBuffered + len;
+    DEBUG_PRINTLN(F("Bootloader size exceeds maximum!"));
+    context->errorMessage = "Bootloader file too large: " + String(totalSize) + " bytes (max: " + String(context->maxBootloaderSize) + " bytes)";
+    return;
+  }
+
+  // Only write to flash when upload is complete
+  if (isFinal) {
+    DEBUG_PRINTLN(F("Bootloader Upload Complete - validating and flashing"));
+
+    if (context->buffer && context->bytesBuffered > 0) {
+      // Verify the complete bootloader image before flashing
+      if (!verifyBootloaderImage(context->buffer, context->bytesBuffered, &context->errorMessage)) {
+        DEBUG_PRINTLN(F("Bootloader validation failed!"));
+        // Error message already set by verifyBootloaderImage
+      } else {
+        // Erase bootloader region
+        DEBUG_PRINTLN(F("Erasing bootloader region..."));
+        esp_err_t err = esp_flash_erase_region(NULL, context->bootloaderOffset, context->maxBootloaderSize);
+        if (err != ESP_OK) {
+          DEBUG_PRINTF_P(PSTR("Bootloader erase error: %d\n"), err);
+          context->errorMessage = "Flash erase failed (error code: " + String(err) + ")";
+        } else {
+          // Write buffered data to flash
+          err = esp_flash_write(NULL, context->buffer, context->bootloaderOffset, context->bytesBuffered);
+          if (err != ESP_OK) {
+            DEBUG_PRINTF_P(PSTR("Bootloader flash write error: %d\n"), err);
+            context->errorMessage = "Flash write failed (error code: " + String(err) + ")";
+          } else {
+            DEBUG_PRINTF_P(PSTR("Bootloader Update Success - %d bytes written\n"), context->bytesBuffered);
+            // Invalidate cached bootloader hash
+            invalidateBootloaderSHA256Cache();
+            context->uploadComplete = true;
+          }
+        }
+      }
+    } else if (context->bytesBuffered == 0) {
+      context->errorMessage = "No bootloader data received";
+    }
+  }
+}
 #endif
diff --git a/wled00/wled_server.cpp b/wled00/wled_server.cpp
index 79cf3d18..9245d17f 100644
--- a/wled00/wled_server.cpp
+++ b/wled00/wled_server.cpp
@@ -244,6 +244,11 @@ String getBootloaderSHA256Hex() {
   return String(hex);
 }
 
+// Invalidate cached bootloader SHA256 (call after bootloader update)
+void invalidateBootloaderSHA256Cache() {
+  bootloaderSHA256Cached = false;
+}
+
 #endif
 
 static void handleUpload(AsyncWebServerRequest *request, const String& filename, size_t index, uint8_t *data, size_t len, bool isFinal) {
@@ -596,145 +601,47 @@ void initServer()
 #if defined(ARDUINO_ARCH_ESP32) && !defined(WLED_DISABLE_OTA)
   // ESP32 bootloader update endpoint
   server.on(F("/updatebootloader"), HTTP_POST, [](AsyncWebServerRequest *request){
-    static String bootloaderErrorMsg = "";
-
-    if (!correctPIN) {
-      serveSettings(request, true); // handle PIN page POST request
-      return;
-    }
-    if (otaLock) {
-      serveMessage(request, 401, FPSTR(s_accessdenied), FPSTR(s_unlock_ota), 254);
-      return;
-    }
-    if (Update.hasError() || !bootloaderErrorMsg.isEmpty()) {
-      String errorDetail = bootloaderErrorMsg.isEmpty() ? F("Please check your file and retry!") : bootloaderErrorMsg;
-      serveMessage(request, 500, F("Bootloader update failed!"), errorDetail.c_str(), 254);
-      bootloaderErrorMsg = ""; // Clear error for next attempt
+    if (request->_tempObject) {
+      auto bootloader_result = getBootloaderOTAResult(request);
+      if (bootloader_result.first) {
+        if (bootloader_result.second.length() > 0) {
+          serveMessage(request, 500, F("Bootloader update failed!"), bootloader_result.second, 254);
+        } else {
+          serveMessage(request, 200, F("Bootloader updated successfully!"), FPSTR(s_rebooting), 131);
+        }
+      }
     } else {
-      serveMessage(request, 200, F("Bootloader updated successfully!"), FPSTR(s_rebooting), 131);
-      doReboot = true;
+      // No context structure - something's gone horribly wrong
+      serveMessage(request, 500, F("Bootloader update failed!"), F("Internal server fault"), 254);
     }
   },[](AsyncWebServerRequest *request, String filename, size_t index, uint8_t *data, size_t len, bool isFinal){
-    static String bootloaderErrorMsg = "";
-    IPAddress client = request->client()->remoteIP();
-    if (((otaSameSubnet && !inSameSubnet(client)) && !strlen(settingsPIN)) || (!otaSameSubnet && !inLocalSubnet(client))) {
-      DEBUG_PRINTLN(F("Attempted bootloader update from different/non-local subnet!"));
-      request->send(401, FPSTR(CONTENT_TYPE_PLAIN), FPSTR(s_accessdenied));
-      return;
-    }
-    if (!correctPIN || otaLock) return;
-
-    static uint8_t* bootloaderBuffer = nullptr;
-    static size_t bootloaderBytesBuffered = 0;
-    const uint32_t bootloaderOffset = 0x1000;
-    // ESP32 bootloader is typically 28-32KB. Use 64KB to be safe while keeping memory reasonable
-    const uint32_t maxBootloaderSize = 0x10000; // 64KB buffer size
-
-    if (!index) {
-      DEBUG_PRINTLN(F("Bootloader Update Start - buffering data"));
-      #if WLED_WATCHDOG_TIMEOUT > 0
-      WLED::instance().disableWatchdog();
-      #endif
-      lastEditTime = millis(); // make sure PIN does not lock during update
-      strip.suspend();
-      strip.resetSegments();
-
-      // Allocate buffer for entire bootloader
-      if (bootloaderBuffer) {
-        free(bootloaderBuffer);
-        bootloaderBuffer = nullptr;
+    if (index == 0) {
+      // Allocate the context structure
+      if (!initBootloaderOTA(request)) {
+        return; // Error will be dealt with after upload in response handler, above
       }
 
-      // Check available heap before attempting allocation
-      size_t freeHeap = getFreeHeapSize();
-      DEBUG_PRINTF_P(PSTR("Free heap before bootloader buffer allocation: %d bytes (need %d bytes)\n"), freeHeap, maxBootloaderSize);
-
-      bootloaderBuffer = (uint8_t*)malloc(maxBootloaderSize);
-      if (!bootloaderBuffer) {
-        size_t freeHeapNow = getFreeHeapSize();
-        DEBUG_PRINTF_P(PSTR("Failed to allocate %d byte bootloader buffer! Free heap: %d bytes\n"), maxBootloaderSize, freeHeapNow);
-        bootloaderErrorMsg = "Out of memory! Free heap: " + String(freeHeapNow) + " bytes, need: " + String(maxBootloaderSize) + " bytes";
-        strip.resume();
-        #if WLED_WATCHDOG_TIMEOUT > 0
-        WLED::instance().enableWatchdog();
-        #endif
-        Update.abort();
+      // Privilege checks
+      IPAddress client = request->client()->remoteIP();
+      if (((otaSameSubnet && !inSameSubnet(client)) && !strlen(settingsPIN)) || (!otaSameSubnet && !inLocalSubnet(client))) {
+        DEBUG_PRINTLN(F("Attempted bootloader update from different/non-local subnet!"));
+        serveMessage(request, 401, FPSTR(s_accessdenied), F("Client is not on local subnet."), 254);
+        setBootloaderOTAReplied(request);
         return;
       }
-      bootloaderBytesBuffered = 0;
-      bootloaderErrorMsg = ""; // Clear any previous errors
-    }
-
-    // Buffer the incoming data
-    if (bootloaderBuffer && bootloaderBytesBuffered + len <= maxBootloaderSize) {
-      memcpy(bootloaderBuffer + bootloaderBytesBuffered, data, len);
-      bootloaderBytesBuffered += len;
-      DEBUG_PRINTF(PSTR("Bootloader buffer progress: %d / %d bytes\n"), bootloaderBytesBuffered, maxBootloaderSize);
-    } else if (!bootloaderBuffer) {
-      DEBUG_PRINTLN(F("Bootloader buffer not allocated!"));
-      bootloaderErrorMsg = "Internal error: Bootloader buffer not allocated";
-      Update.abort();
-    } else {
-      size_t totalSize = bootloaderBytesBuffered + len;
-      DEBUG_PRINTLN(F("Bootloader size exceeds maximum!"));
-      bootloaderErrorMsg = "Bootloader file too large: " + String(totalSize) + " bytes (max: " + String(maxBootloaderSize) + " bytes)";
-      if (bootloaderBuffer) {
-        free(bootloaderBuffer);
-        bootloaderBuffer = nullptr;
+      if (!correctPIN) {
+        serveMessage(request, 401, FPSTR(s_accessdenied), FPSTR(s_unlock_cfg), 254);
+        setBootloaderOTAReplied(request);
+        return;
       }
-      Update.abort();
-    }
-
-    // Only write to flash when upload is complete
-    if (isFinal) {
-      bool success = false;
-      if (!Update.hasError() && bootloaderBuffer && bootloaderBytesBuffered > 0) {
-        DEBUG_PRINTF_P(PSTR("Bootloader buffered (%d bytes) - validating\n"), bootloaderBytesBuffered);
-
-        // Verify the complete bootloader image before flashing
-        if (!verifyBootloaderImage(bootloaderBuffer, bootloaderBytesBuffered, &bootloaderErrorMsg)) {
-          DEBUG_PRINTLN(F("Bootloader validation failed!"));
-          // Error message already set by verifyBootloaderImage
-        } else {
-          // Erase bootloader region
-          DEBUG_PRINTLN(F("Erasing bootloader region..."));
-          esp_err_t err = esp_flash_erase_region(NULL, bootloaderOffset, maxBootloaderSize);
-          if (err != ESP_OK) {
-            DEBUG_PRINTF_P(PSTR("Bootloader erase error: %d\n"), err);
-            bootloaderErrorMsg = "Flash erase failed (error code: " + String(err) + ")";
-          } else {
-            // Write buffered data to flash
-            err = esp_flash_write(NULL, bootloaderBuffer, bootloaderOffset, bootloaderBytesBuffered);
-            if (err != ESP_OK) {
-              DEBUG_PRINTF_P(PSTR("Bootloader flash write error: %d\n"), err);
-              bootloaderErrorMsg = "Flash write failed (error code: " + String(err) + ")";
-            } else {
-              DEBUG_PRINTF_P(PSTR("Bootloader Update Success - %d bytes written\n"), bootloaderBytesBuffered);
-              bootloaderSHA256Cached = false; // Invalidate cached bootloader hash
-              success = true;
-            }
-          }
-        }
-      } else if (bootloaderBytesBuffered == 0) {
-        bootloaderErrorMsg = "No bootloader data received";
-      }
-
-      // Cleanup
-      if (bootloaderBuffer) {
-        free(bootloaderBuffer);
-        bootloaderBuffer = nullptr;
-      }
-      bootloaderBytesBuffered = 0;
-
-      if (!success) {
-        DEBUG_PRINTLN(F("Bootloader Update Failed"));
-        serveMessage(request, 500, F("Bootloader upgrade failed!"), bootloaderErrorMsg, 254);
-        strip.resume();
-        #if WLED_WATCHDOG_TIMEOUT > 0
-        WLED::instance().enableWatchdog();
-        #endif
+      if (otaLock) {
+        serveMessage(request, 401, FPSTR(s_accessdenied), FPSTR(s_unlock_ota), 254);
+        setBootloaderOTAReplied(request);
+        return;
       }
     }
+
+    handleBootloaderOTAData(request, index, data, len, isFinal);
   });
 #endif