diff --git a/static/settings_editor.html b/static/settings_editor.html
index c714c27..d7ce41b 100644
--- a/static/settings_editor.html
+++ b/static/settings_editor.html
@@ -185,10 +185,11 @@
         document.body.getAttribute('data-api-base') ??
         (location.pathname.includes('/led-tool') ? '/led-tool' : '');
       const prefix = api + '/static';
+      const v = '20260520';
       function loadScript(url) {
         return new Promise((resolve, reject) => {
           const s = document.createElement('script');
-          s.src = url;
+          s.src = url + (url.includes('?') ? '&' : '?') + 'v=' + v;
           s.onload = () => resolve();
           s.onerror = () => reject(new Error('Failed to load ' + url));
           document.body.appendChild(s);
diff --git a/static/settings_editor.js b/static/settings_editor.js
index a354ac1..f3ab2bf 100644
--- a/static/settings_editor.js
+++ b/static/settings_editor.js
@@ -24,8 +24,10 @@
   let hostConnected = false;
   let hostConnectedPort = '';
   let transferBusy = false;
+  let webConnectBusy = false;
 
   const webSerialOk = window.LedToolWebSerial && window.LedToolWebSerial.supported();
+  let webSerialGrantedCount = 0;
 
   function setStatus(text, isError) {
     if (!statusEl) return;
@@ -40,6 +42,17 @@
     setTimeout(() => messageEl.classList.remove('show'), 5000);
   }
 
+  function errorMessage(e) {
+    if (!e) return 'Unknown error';
+    if (typeof e === 'string') return e;
+    return e.message || String(e);
+  }
+
+  function onWebSerialTransferError(e) {
+    if (webClient) webClient.inRawRepl = false;
+    return errorMessage(e);
+  }
+
   function formToObject() {
     const out = {};
     document.querySelectorAll('[data-setting]').forEach((el) => {
@@ -99,7 +112,11 @@
     } else if (hostOpen) {
       setStatus(`Host serial: ${hostConnectedPort} (use Download or Upload).`);
     } else if (webSerialOk) {
-      setStatus('Connect host serial or Web Serial USB, then Download or Upload.');
+      if (webSerialGrantedCount === 1) {
+        setStatus('Connect USB (one remembered port) or host serial, then Download or Upload.');
+      } else {
+        setStatus('Connect host serial or Web Serial USB, then Download or Upload.');
+      }
     } else {
       setStatus(`Connect host serial (default ${DEFAULT_HOST_PORT}).`);
     }
@@ -205,21 +222,31 @@
   }
 
   async function connectWebSerial() {
+    if (webConnectBusy) return;
     if (!window.LedToolWebSerial || !window.LedToolWebSerial.supported()) {
       flash('Web Serial not supported (use Chrome or Edge over HTTPS or localhost).', true);
       return;
     }
+    if (usingWebSerial()) {
+      flash('USB already connected.', false);
+      return;
+    }
     if (usingHostSerial()) {
       disconnectHostSerial();
     }
-    log('connectWebSerial: requestPort');
-    setStatus('Opening USB port…');
-    webPort = await window.LedToolWebSerial.requestPort();
-    log('connectWebSerial: port selected', webPort);
-    webClient = new window.LedToolWebSerial.MicroPythonRawRepl();
-    await webClient.connect(webPort);
-    updateUi();
-    flash('USB port open. Use Download or Upload to talk to the device.', false);
+    webConnectBusy = true;
+    try {
+      log('connectWebSerial: requestPort');
+      setStatus('Opening USB port…');
+      webPort = await window.LedToolWebSerial.requestPort();
+      log('connectWebSerial: port selected', webPort);
+      webClient = new window.LedToolWebSerial.MicroPythonRawRepl();
+      await webClient.connect(webPort);
+      updateUi();
+      flash('USB port open. Wait for boot, then Download.', false);
+    } finally {
+      webConnectBusy = false;
+    }
   }
 
   async function disconnectWebSerial() {
@@ -284,9 +311,10 @@
       }
     } catch (e) {
       console.error(LOG, 'download failed', e);
-      if (rawJson) rawJson.value = String(e.message || e);
-      flash(e.message, true);
-      setStatus(e.message, true);
+      const msg = usingWebSerial() ? onWebSerialTransferError(e) : errorMessage(e);
+      if (rawJson) rawJson.value = msg;
+      flash(msg, true);
+      setStatus(msg, true);
     } finally {
       transferBusy = false;
     }
@@ -310,8 +338,9 @@
       }
     } catch (e) {
       console.error(LOG, 'upload failed', e);
-      flash(e.message, true);
-      setStatus(e.message, true);
+      const msg = usingWebSerial() ? onWebSerialTransferError(e) : errorMessage(e);
+      flash(msg, true);
+      setStatus(msg, true);
     } finally {
       transferBusy = false;
     }
@@ -374,7 +403,19 @@
     }
   });
 
+  async function refreshWebSerialGrantHint() {
+    if (!webSerialOk || !window.LedToolWebSerial.getGrantedPorts) return;
+    try {
+      const ports = await window.LedToolWebSerial.getGrantedPorts();
+      webSerialGrantedCount = ports.length;
+      updateUi();
+    } catch (_) {
+      /* ignore */
+    }
+  }
+
   log('settings editor ready', { apiBase, webSerialOk });
   updateUi();
   loadHostPorts();
+  refreshWebSerialGrantHint();
 })();
diff --git a/static/web_serial.js b/static/web_serial.js
index 14c1624..7931f4d 100644
--- a/static/web_serial.js
+++ b/static/web_serial.js
@@ -3,7 +3,7 @@
  */
 (function (global) {
   const RAW_REPL_BANNER = 'raw REPL; CTRL-B to exit\r\n';
-  const SOFT_REBOOT = 'soft reboot\r\n';
+  const SOFT_REBOOT_MARKERS = ['soft reboot\r\n', 'MPY: soft reboot\r\n'];
   const LOG = '[led-tool/serial]';
 
   function log(...args) {
@@ -29,12 +29,65 @@
     return new Promise((resolve) => setTimeout(resolve, ms));
   }
 
-  function bytesEndsWith(buf, suffix) {
-    if (buf.length < suffix.length) return false;
-    for (let i = 0; i < suffix.length; i += 1) {
-      if (buf[buf.length - suffix.length + i] !== suffix[i]) return false;
+  /** Common ESP32 USB-UART bridges (usbVendorId only per Web Serial API). */
+  const ESP32_USB_FILTERS = [
+    { usbVendorId: 0x303a }, /* Espressif */
+    { usbVendorId: 0x10c4 }, /* Silicon Labs CP210x */
+    { usbVendorId: 0x1a86 }, /* WCH CH340 */
+    { usbVendorId: 0x0403 }, /* FTDI */
+  ];
+
+  async function deassertDtrRts(port) {
+    if (!port || !port.setSignals) return;
+    try {
+      await port.setSignals({ dataTerminalReady: false, requestToSend: false });
+    } catch (_) {
+      /* ignore — some adapters/browsers reject setSignals */
     }
-    return true;
+  }
+
+  function bytesIndexOf(buf, suffix) {
+    if (!suffix.length) return 0;
+    if (buf.length < suffix.length) return -1;
+    for (let i = 0; i <= buf.length - suffix.length; i += 1) {
+      let ok = true;
+      for (let j = 0; j < suffix.length; j += 1) {
+        if (buf[i + j] !== suffix[j]) {
+          ok = false;
+          break;
+        }
+      }
+      if (ok) return i;
+    }
+    return -1;
+  }
+
+  function bufferEndsWithFriendlyRepl(buf) {
+    if (bufferLooksLikeEspRomBoot(buf) && !bufferHasMicroPython(buf)) return false;
+    const tail = decodeText(Uint8Array.from(buf.slice(-80)));
+    return /(?:\r\n|\n)>>> ?$/.test(tail);
+  }
+
+  function bufferLooksLikeEspRomBoot(buf) {
+    if (bufferIndicatesRuntime(buf)) return false;
+    const text = decodeText(Uint8Array.from(buf.slice(-512)));
+    return /SPI_FAST_FLASH_BOOT|rst:0x/.test(text) && !/entry 0x403/.test(text);
+  }
+
+  /** MicroPython is up (banner, REPL, raw REPL, or post-ROM heap lines from boot). */
+  function bufferIndicatesRuntime(buf) {
+    const text = decodeText(Uint8Array.from(buf));
+    if (text.includes('MicroPython')) return true;
+    if (text.includes('raw REPL; CTRL-B to exit')) return true;
+    if (/(?:\r\n|\n)>>> ?/.test(text)) return true;
+    if (text.includes('entry 0x') && (/['"]?free['"]?\s*:/.test(text) || /,\s*'free'/.test(text))) {
+      return true;
+    }
+    return false;
+  }
+
+  function bufferHasMicroPython(buf) {
+    return bufferIndicatesRuntime(buf);
   }
 
   function decodeText(u8) {
@@ -84,12 +137,15 @@
       return result.value || null;
     }
 
+    /** Match suffix anywhere in the buffer; keep bytes after the match for the next read. */
     async readUntil(suffixBytes, timeoutMs = 15000) {
       const deadline = Date.now() + timeoutMs;
       while (Date.now() < deadline) {
-        if (bytesEndsWith(this._rxBuf, suffixBytes)) {
-          const matched = Uint8Array.from(this._rxBuf);
-          this._rxBuf.length = 0;
+        const idx = bytesIndexOf(this._rxBuf, suffixBytes);
+        if (idx >= 0) {
+          const end = idx + suffixBytes.length;
+          const matched = Uint8Array.from(this._rxBuf.slice(0, end));
+          this._rxBuf.splice(0, end);
           logDebug('readUntil matched', JSON.stringify(decodeText(suffixBytes)), 'len', matched.length);
           return matched;
         }
@@ -106,6 +162,29 @@
       throw new Error(err);
     }
 
+    async readUntilAny(suffixList, timeoutMs = 15000) {
+      const deadline = Date.now() + timeoutMs;
+      while (Date.now() < deadline) {
+        for (const suffixBytes of suffixList) {
+          const idx = bytesIndexOf(this._rxBuf, suffixBytes);
+          if (idx >= 0) {
+            const end = idx + suffixBytes.length;
+            const matched = Uint8Array.from(this._rxBuf.slice(0, end));
+            this._rxBuf.splice(0, end);
+            logDebug('readUntilAny matched', JSON.stringify(decodeText(suffixBytes)));
+            return matched;
+          }
+        }
+        const chunk = await this._readStreamChunk(Math.min(300, Math.max(1, deadline - Date.now())));
+        if (chunk && chunk.length) this._appendRx(chunk);
+        else await sleep(5);
+      }
+      const tail = decodeText(Uint8Array.from(this._rxBuf.slice(-240)));
+      throw new Error(
+        `Timed out waiting for one of ${suffixList.map((s) => JSON.stringify(decodeText(s))).join(', ')} (tail: ${JSON.stringify(tail)})`,
+      );
+    }
+
     async readExact(n, timeoutMs = 10000) {
       const deadline = Date.now() + timeoutMs;
       while (this._rxBuf.length < n && Date.now() < deadline) {
@@ -132,21 +211,38 @@
         flowControl: 'none',
         bufferSize: 65536,
       });
-      if (this.port.setSignals) {
-        try {
-          await this.port.setSignals({ dataTerminalReady: false, requestToSend: false });
-        } catch (_) {
-          /* ignore */
-        }
-      }
+      await deassertDtrRts(this.port);
+      await sleep(50);
+      await deassertDtrRts(this.port);
       this.reader = this.port.readable.getReader();
       this.writer = this.port.writable.getWriter();
       this.portOpen = true;
       await sleep(100);
-      await this.drainInput(300);
+      await this.collectIncoming(8000);
+      if (bufferIndicatesRuntime(this._rxBuf)) {
+        log('connect: MicroPython output seen during open');
+      }
       log('connect: port open (raw REPL not entered yet)');
     }
 
+    /** Read serial into _rxBuf without discarding (for post-open boot). */
+    async collectIncoming(maxMs) {
+      const deadline = Date.now() + maxMs;
+      while (Date.now() < deadline) {
+        const chunk = await this._readStreamChunk(Math.min(80, Math.max(1, deadline - Date.now())));
+        if (chunk && chunk.length) this._appendRx(chunk);
+        else if (
+          bufferHasMicroPython(this._rxBuf) ||
+          bufferEndsWithFriendlyRepl(this._rxBuf) ||
+          bytesIndexOf(this._rxBuf, new TextEncoder().encode(RAW_REPL_BANNER)) >= 0
+        ) {
+          break;
+        } else {
+          await sleep(15);
+        }
+      }
+    }
+
     async ensureRawRepl() {
       if (this.inRawRepl) return;
       if (this._replLock) {
@@ -154,7 +250,8 @@
         return;
       }
       log('ensureRawRepl: entering raw REPL');
-      this._replLock = this.enterRawRepl(true).finally(() => {
+      // USB open already resets the ESP32; skip soft-reset (unlike host led-cli/mpremote).
+      this._replLock = this.enterRawRepl(false).finally(() => {
         this._replLock = null;
       });
       await this._replLock;
@@ -193,6 +290,11 @@
         this.writer = null;
       }
       if (this.port) {
+        try {
+          await deassertDtrRts(this.port);
+        } catch (_) {
+          /* ignore */
+        }
         try {
           await this.port.close();
         } catch (_) {
@@ -209,41 +311,147 @@
       await this.writer.write(data);
     }
 
-    async drainInput(maxMs = 400) {
+    async drainInput(maxMs = 400, clearBuffer = true) {
       const deadline = Date.now() + maxMs;
       while (Date.now() < deadline) {
         const chunk = await this._readStreamChunk(40);
         if (!chunk || !chunk.length) break;
+        if (!clearBuffer && chunk.length) this._appendRx(chunk);
       }
-      this._rxBuf.length = 0;
+      if (clearBuffer) this._rxBuf.length = 0;
+    }
+
+    async sendCtrlA() {
+      await this.writeBytes(new Uint8Array([0x0d, 0x01]));
+    }
+
+    /** USB open often resets the ESP32; wait through ROM boot until MicroPython is up. */
+    async waitForMicroPythonBoot(timeoutMs = 60000) {
+      log('enterRawRepl: wait for MicroPython after boot', 'buf', this._rxBuf.length);
+      if (bufferHasMicroPython(this._rxBuf) || bufferEndsWithFriendlyRepl(this._rxBuf)) {
+        log('enterRawRepl: MicroPython already in buffer');
+        return;
+      }
+      const deadline = Date.now() + timeoutMs;
+      let nudgeSent = false;
+      let lastLog = Date.now();
+      while (Date.now() < deadline) {
+        if (bufferHasMicroPython(this._rxBuf) || bufferEndsWithFriendlyRepl(this._rxBuf)) {
+          log('enterRawRepl: MicroPython running');
+          return;
+        }
+        const text = decodeText(Uint8Array.from(this._rxBuf));
+        if (!nudgeSent && text.includes('entry 0x')) {
+          nudgeSent = true;
+          log('enterRawRepl: past ROM loader, nudge REPL');
+          await this.writeBytes(new Uint8Array([0x0d]));
+          await sleep(200);
+        }
+        if (Date.now() - lastLog > 5000) {
+          lastLog = Date.now();
+          log('enterRawRepl: still waiting…', 'buf', this._rxBuf.length);
+        }
+        const rem = Math.max(1, deadline - Date.now());
+        const chunk = await this._readStreamChunk(Math.min(300, rem));
+        if (chunk && chunk.length) this._appendRx(chunk);
+        else await sleep(bufferLooksLikeEspRomBoot(this._rxBuf) ? 20 : 10);
+      }
+      const tail = decodeText(Uint8Array.from(this._rxBuf.slice(-240)));
+      throw new Error(`Timed out waiting for MicroPython boot (tail: ${JSON.stringify(tail)})`);
+    }
+
+    /** Wait until raw REPL banner and `>` prompt (not banner alone — device may still be booting). */
+    async waitRawReplAfterSoftReboot(bannerBytes, bannerPromptBytes, timeoutMs = 15000) {
+      const deadline = Date.now() + timeoutMs;
+      while (Date.now() < deadline) {
+        const rem = Math.max(1, deadline - Date.now());
+        const promptAt = bytesIndexOf(this._rxBuf, bannerPromptBytes);
+        if (promptAt >= 0) {
+          this._rxBuf.splice(0, promptAt + bannerPromptBytes.length);
+          log('enterRawRepl: raw REPL prompt ready');
+          return;
+        }
+        if (bufferEndsWithFriendlyRepl(this._rxBuf)) {
+          log('enterRawRepl: friendly REPL, ctrl-A');
+          await this.sendCtrlA();
+          await sleep(30);
+          continue;
+        }
+        if (bufferLooksLikeEspRomBoot(this._rxBuf) && !bufferHasMicroPython(this._rxBuf)) {
+          logDebug('enterRawRepl: ROM boot in progress…');
+        }
+        const chunk = await this._readStreamChunk(Math.min(300, rem));
+        if (chunk && chunk.length) this._appendRx(chunk);
+        else await sleep(10);
+      }
+      const tail = decodeText(Uint8Array.from(this._rxBuf.slice(-240)));
+      throw new Error(
+        `Timed out waiting for raw REPL after soft reboot (tail: ${JSON.stringify(tail)})`,
+      );
     }
 
     /** Match mpremote SerialTransport.enter_raw_repl(soft_reset). */
     async enterRawRepl(softReset = true) {
       log('enterRawRepl', { softReset });
-      await this.writeBytes(new Uint8Array([0x0d, 0x03]));
-      await this.drainInput(400);
-      await this.writeBytes(new Uint8Array([0x0d, 0x01]));
+      const bannerBytes = new TextEncoder().encode(RAW_REPL_BANNER);
+      const bannerPromptBytes = new TextEncoder().encode(RAW_REPL_BANNER + '>');
+      const softRebootBytes = SOFT_REBOOT_MARKERS.map((m) => new TextEncoder().encode(m));
 
-      if (softReset) {
-        log('enterRawRepl: wait banner+>, soft reset');
-        await this.readUntil(new TextEncoder().encode(RAW_REPL_BANNER + '>'), 15000);
-        await this.writeBytes(new Uint8Array([0x04]));
+      if (
+        !bufferHasMicroPython(this._rxBuf) &&
+        !bufferEndsWithFriendlyRepl(this._rxBuf) &&
+        bytesIndexOf(this._rxBuf, bannerBytes) < 0
+      ) {
+        await this.waitForMicroPythonBoot(60000);
+      } else {
+        log('enterRawRepl: already have REPL output in buffer');
+      }
+
+      if (bufferEndsWithFriendlyRepl(this._rxBuf)) {
+        await this.writeBytes(new Uint8Array([0x0d, 0x03]));
+        await sleep(50);
+      }
+
+      let ctrlARetries = 0;
+      const maxCtrlARetries = 3;
+      while (ctrlARetries <= maxCtrlARetries) {
         try {
-          await this.readUntil(new TextEncoder().encode(SOFT_REBOOT), 15000);
-          log('enterRawRepl: saw soft reboot');
+          await this.sendCtrlA();
+          await this.waitRawReplAfterSoftReboot(bannerBytes, bannerPromptBytes, 20000);
+          break;
         } catch (e) {
-          log('enterRawRepl: no soft reboot banner', e.message);
+          if (ctrlARetries >= maxCtrlARetries) throw e;
+          ctrlARetries += 1;
+          log('enterRawRepl: retry ctrl-A', ctrlARetries, e.message);
+          this._rxBuf.length = 0;
         }
       }
 
-      try {
-        await this.readUntil(new TextEncoder().encode(RAW_REPL_BANNER), 45000);
-      } catch (e) {
-        log('enterRawRepl: retry ctrl-A after', e.message);
-        await this.writeBytes(new Uint8Array([0x0d, 0x01]));
-        await this.readUntil(new TextEncoder().encode(RAW_REPL_BANNER), 30000);
+      if (softReset) {
+        log('enterRawRepl: soft reset');
+        await this.writeBytes(new Uint8Array([0x04]));
+        try {
+          await this.readUntilAny(softRebootBytes, 20000);
+          log('enterRawRepl: saw soft reboot');
+          this._rxBuf.length = 0;
+        } catch (e) {
+          log('enterRawRepl: no soft reboot banner', e.message);
+        }
+        ctrlARetries = 0;
+        while (ctrlARetries <= maxCtrlARetries) {
+          try {
+            await this.waitRawReplAfterSoftReboot(bannerBytes, bannerPromptBytes, 60000);
+            break;
+          } catch (e) {
+            if (ctrlARetries >= maxCtrlARetries) throw e;
+            ctrlARetries += 1;
+            log('enterRawRepl: post-reboot retry ctrl-A', ctrlARetries, e.message);
+            this._rxBuf.length = 0;
+            await this.sendCtrlA();
+          }
+        }
       }
+
       this.inRawRepl = true;
       log('enterRawRepl: ready');
     }
@@ -275,9 +483,34 @@
       await this.readUntil(new Uint8Array([0x04]), 30000);
     }
 
+    async awaitRawReplExecPrompt(timeoutMs = 60000) {
+      const bannerPromptBytes = new TextEncoder().encode(RAW_REPL_BANNER + '>');
+      const deadline = Date.now() + timeoutMs;
+      while (Date.now() < deadline) {
+        const promptAt = bytesIndexOf(this._rxBuf, bannerPromptBytes);
+        if (promptAt >= 0) {
+          this._rxBuf.splice(0, promptAt + bannerPromptBytes.length);
+          return;
+        }
+        if (bufferEndsWithFriendlyRepl(this._rxBuf)) {
+          log('exec: friendly REPL before prompt, ctrl-A');
+          this._rxBuf.length = 0;
+          await this.sendCtrlA();
+        } else if (bufferLooksLikeEspRomBoot(this._rxBuf)) {
+          logDebug('exec: still in ROM boot, waiting…');
+        }
+        const rem = Math.max(1, deadline - Date.now());
+        const chunk = await this._readStreamChunk(Math.min(300, rem));
+        if (chunk && chunk.length) this._appendRx(chunk);
+        else await sleep(10);
+      }
+      const tail = decodeText(Uint8Array.from(this._rxBuf.slice(-240)));
+      throw new Error(`Timed out waiting for raw REPL prompt (tail: ${JSON.stringify(tail)})`);
+    }
+
     async execRawNoFollow(commandBytes) {
       log('execRawNoFollow', commandBytes.length, 'bytes');
-      await this.readUntil(new TextEncoder().encode('>'), 10000);
+      await this.awaitRawReplExecPrompt(60000);
 
       if (this.useRawPaste) {
         await this.writeBytes(new Uint8Array([0x05, 0x41, 0x01]));
@@ -388,9 +621,33 @@
     }
   }
 
+  function serialSupported() {
+    return typeof navigator !== 'undefined' && 'serial' in navigator;
+  }
+
+  async function getGrantedPorts() {
+    if (!serialSupported()) return [];
+    return navigator.serial.getPorts();
+  }
+
+  async function requestPort() {
+    if (!serialSupported()) {
+      throw new Error('Web Serial not supported');
+    }
+    const granted = await navigator.serial.getPorts();
+    if (granted.length === 1) {
+      log('requestPort: reusing single granted port');
+      return granted[0];
+    }
+    log('requestPort: showing picker', { grantedCount: granted.length });
+    return navigator.serial.requestPort({ filters: ESP32_USB_FILTERS });
+  }
+
   global.LedToolWebSerial = {
-    supported: () => typeof navigator !== 'undefined' && 'serial' in navigator,
-    requestPort: () => navigator.serial.requestPort(),
+    supported: serialSupported,
+    getGrantedPorts,
+    requestPort,
     MicroPythonRawRepl,
+    _test: { bytesIndexOf, decodeText },
   };
 })(typeof window !== 'undefined' ? window : globalThis);