diff --git a/docs/architecture.md b/docs/architecture.md
index 5b492eb01..62f80b63b 100644
--- a/docs/architecture.md
+++ b/docs/architecture.md
@@ -252,6 +252,10 @@ Terminal I/O is sent as binary WebSocket frames decoded by `decodeTerminalStream
 Terminal PTY size is last-interacting-client-wins. A client claims the PTY size only when its terminal viewport genuinely changes size or the user focuses/taps the terminal. Passive rendering work — attaching, restoring visibility, font settling, renderer refits, or just looking at a visible terminal — must not send a resize frame. The server does not broadcast resize ownership; the resized PTY redraws through normal output, and every attached client renders that output in its own local viewport.
 
 There is also a separate file-transfer binary frame format in the same directory, used for download/upload streams.
+File downloads keep the existing `FileBegin`/`FileChunk`/`FileEnd` framing and stream 256 KiB chunks
+from one stable file handle. Each transfer awaits completion of its own physical WebSocket send before
+reading the next chunk; it is scoped to the requesting physical socket and does not queue unrelated
+messages or transfers.
 
 ### Compatibility rules
 
diff --git a/packages/relay/src/encrypted-channel.test.ts b/packages/relay/src/encrypted-channel.test.ts
index 90ef5e0e3..b2f79c494 100644
--- a/packages/relay/src/encrypted-channel.test.ts
+++ b/packages/relay/src/encrypted-channel.test.ts
@@ -1,5 +1,10 @@
 import { describe, it, expect, vi } from "vitest";
-import { createClientChannel, createDaemonChannel, Transport } from "./encrypted-channel.js";
+import {
+  createClientChannel,
+  createDaemonChannel,
+  EncryptedChannel,
+  Transport,
+} from "./encrypted-channel.js";
 import {
   deriveSharedKey,
   encrypt,
@@ -47,6 +52,64 @@ async function waitForAsyncDelivery(): Promise<void> {
 }
 
 describe("EncryptedChannel", () => {
+  it("rejects the daemon handshake when the ready frame fails to send", async () => {
+    const daemonKeyPair = generateKeyPair();
+    const clientKeyPair = generateKeyPair();
+    const transport: Transport = {
+      send: () => Promise.reject(new Error("ready send failed")),
+      close: () => undefined,
+      onmessage: null,
+      onclose: null,
+      onerror: null,
+    };
+    const channel = createDaemonChannel(transport, daemonKeyPair);
+
+    transport.onmessage?.({
+      data: JSON.stringify({
+        type: "e2ee_hello",
+        key: exportPublicKey(clientKeyPair.publicKey),
+      }),
+      isBinary: false,
+    });
+
+    await expect(channel).rejects.toThrow("ready send failed");
+  });
+
+  it("waits for transport send completion", async () => {
+    let completeSend: (() => void) | undefined;
+    const transport: Transport = {
+      send: () =>
+        new Promise<void>((resolve) => {
+          completeSend = resolve;
+        }),
+      close: () => undefined,
+      onmessage: null,
+      onclose: null,
+      onerror: null,
+    };
+    const first = generateKeyPair();
+    const second = generateKeyPair();
+    const channel = new EncryptedChannel(
+      transport,
+      deriveSharedKey(first.secretKey, second.publicKey),
+      {},
+      { binaryCiphertext: true },
+    );
+    channel.setState("open");
+    let completed = false;
+
+    const sending = channel.send(new Uint8Array([1, 2, 3]).buffer).then(() => {
+      completed = true;
+      return undefined;
+    });
+    await Promise.resolve();
+    expect(completed).toBe(false);
+
+    completeSend?.();
+    await sending;
+    expect(completed).toBe(true);
+  });
+
   it("establishes encrypted channel between daemon and client", async () => {
     const [daemonTransport, clientTransport] = createMockTransportPair();
 
@@ -191,6 +254,58 @@ describe("EncryptedChannel", () => {
     }
   });
 
+  it("reports rejected handshake hello sends", async () => {
+    const daemonKeyPair = generateKeyPair();
+    const daemonPubKeyB64 = exportPublicKey(daemonKeyPair.publicKey);
+    const transport: Transport = {
+      send: () => Promise.reject(new Error("hello send failed")),
+      close: vi.fn(),
+      onmessage: null,
+      onclose: null,
+      onerror: null,
+    };
+    const onerror = vi.fn();
+
+    await createClientChannel(transport, daemonPubKeyB64, { onerror });
+    await Promise.resolve();
+
+    expect(onerror).toHaveBeenCalledTimes(1);
+    expect((onerror.mock.calls[0][0] as Error).message).toBe("hello send failed");
+    transport.onclose?.(1000, "closed");
+  });
+
+  it("reports rejected sends while flushing the handshake backlog", async () => {
+    const daemonKeyPair = generateKeyPair();
+    const daemonPubKeyB64 = exportPublicKey(daemonKeyPair.publicKey);
+    let sendAttempts = 0;
+    const transport: Transport = {
+      send: () => {
+        sendAttempts += 1;
+        return sendAttempts === 1 ? undefined : Promise.reject(new Error("backlog send failed"));
+      },
+      close: vi.fn(),
+      onmessage: null,
+      onclose: null,
+      onerror: null,
+    };
+    const onerror = vi.fn();
+    const channel = await createClientChannel(transport, daemonPubKeyB64, { onerror });
+    await channel.send(new ArrayBuffer(8));
+
+    transport.onmessage?.({
+      data: JSON.stringify({
+        type: "e2ee_ready",
+        capabilities: { binaryCiphertext: true },
+      }),
+      isBinary: false,
+    });
+    await waitForAsyncDelivery();
+
+    expect(onerror).toHaveBeenCalledTimes(1);
+    expect((onerror.mock.calls[0][0] as Error).message).toBe("backlog send failed");
+    expect(transport.close).toHaveBeenCalledWith(1011, "backlog send failed");
+  });
+
   it("fails handshake on invalid hello", async () => {
     const [daemonTransport] = createMockTransportPair();
 
diff --git a/packages/relay/src/encrypted-channel.ts b/packages/relay/src/encrypted-channel.ts
index f25dc3d05..de953616a 100644
--- a/packages/relay/src/encrypted-channel.ts
+++ b/packages/relay/src/encrypted-channel.ts
@@ -19,7 +19,7 @@ import {
 import { arrayBufferToBase64, base64ToArrayBuffer } from "./base64.js";
 
 export interface Transport {
-  send(data: string | ArrayBuffer): void;
+  send(data: string | ArrayBuffer): void | Promise<void>;
   close(code?: number, reason?: string): void;
   onmessage: ((message: TransportMessage) => void) | null;
   onclose: ((code: number, reason: string) => void) | null;
@@ -169,7 +169,10 @@ export async function createClientChannel(
   };
   const sendHello = () => {
     try {
-      transport.send(helloText);
+      const result = transport.send(helloText);
+      if (result) {
+        void result.catch(emitSendError);
+      }
       return true;
     } catch (error) {
       // This can happen during daemon restarts while the socket transitions
@@ -263,11 +266,7 @@ export async function createDaemonChannel(
         const sharedKey = deriveSharedKey(daemonKeyPair.secretKey, clientPublicKey);
 
         const binaryCiphertext = supportsBinaryCiphertext(msg);
-        const channel = new EncryptedChannel(transport, sharedKey, events, {
-          daemonKeyPair,
-          binaryCiphertext,
-        });
-        transport.send(
+        await transport.send(
           JSON.stringify({
             type: "e2ee_ready",
             ...(binaryCiphertext
@@ -276,6 +275,10 @@ export async function createDaemonChannel(
           } satisfies E2EEReadyMessage),
         );
 
+        const channel = new EncryptedChannel(transport, sharedKey, events, {
+          daemonKeyPair,
+          binaryCiphertext,
+        });
         channel.setState("open");
         events.onopen?.();
 
@@ -354,7 +357,14 @@ export class EncryptedChannel {
           this.state = "open";
           this.events.onopen?.();
           for (const cb of this.onOpenCallbacks) cb();
-          await this.flushPendingSends();
+          try {
+            await this.flushPendingSends();
+          } catch (error) {
+            const err = error instanceof Error ? error : new Error(String(error));
+            this.events.onerror?.(err);
+            this.state = "closed";
+            this.transport.close(1011, err.message);
+          }
         }
       } catch {
         // ignore non-ready handshake traffic
@@ -455,12 +465,12 @@ export class EncryptedChannel {
 
     const ciphertext = encrypt(this.sharedKey, data);
     if (this.options.binaryCiphertext && data instanceof ArrayBuffer) {
-      this.transport.send(ciphertext);
+      await this.transport.send(ciphertext);
       return;
     }
     // COMPAT(binaryCiphertext): added in v0.2.3, remove base64 binary sends
     // after 2027-01-27 once the supported peer floor includes negotiation.
-    this.transport.send(arrayBufferToBase64(ciphertext));
+    await this.transport.send(arrayBufferToBase64(ciphertext));
   }
 
   outboundWireByteLength(data: string | ArrayBuffer): number {
@@ -489,7 +499,7 @@ export class EncryptedChannel {
     // "ready" but do not re-key. Re-keying here would desync
     // the channel and cause decrypt failures.
     if (keysEqual(nextSharedKey, this.sharedKey)) {
-      this.transport.send(
+      await this.transport.send(
         JSON.stringify({
           type: "e2ee_ready",
           ...(this.options.binaryCiphertext
diff --git a/packages/server/src/server/file-explorer/service.test.ts b/packages/server/src/server/file-explorer/service.test.ts
index 1025f395e..07f451e83 100644
--- a/packages/server/src/server/file-explorer/service.test.ts
+++ b/packages/server/src/server/file-explorer/service.test.ts
@@ -1,8 +1,13 @@
-import { chmod, mkdtemp, rm, stat, writeFile } from "node:fs/promises";
+import { appendFile, chmod, mkdtemp, rm, stat, truncate, writeFile } from "node:fs/promises";
 import os from "node:os";
 import path from "node:path";
 import { describe, expect, it } from "vitest";
-import { getExplorerFileVersion, readExplorerFile, writeExplorerFile } from "./service.js";
+import {
+  getExplorerFileVersion,
+  readExplorerFile,
+  streamExplorerFile,
+  writeExplorerFile,
+} from "./service.js";
 
 async function createHomeTempDir(prefix: string): Promise<string> {
   return mkdtemp(path.join(os.homedir(), prefix));
@@ -192,6 +197,127 @@ describe("file explorer service", () => {
     }
   });
 
+  it("fails a stream when the file grows after its revision is advertised", async () => {
+    const root = await createTempDir("paseo-file-stream-growth-");
+
+    try {
+      const filePath = path.join(root, "growing.log");
+      const initial = Buffer.alloc(300 * 1024, 0x61);
+      await writeFile(filePath, initial);
+      await expect(
+        streamExplorerFile({ root, relativePath: "growing.log" }, async (file) => {
+          await appendFile(filePath, Buffer.alloc(300 * 1024, 0x62));
+          for await (const _chunk of file.chunks) {
+            // Consume through the advertised prefix before validating the revision.
+          }
+        }),
+      ).rejects.toThrow("File changed during transfer");
+    } finally {
+      await rm(root, { recursive: true, force: true });
+    }
+  });
+
+  it("fails a stream when the file shrinks below its advertised size", async () => {
+    const root = await createTempDir("paseo-file-stream-truncate-");
+
+    try {
+      const filePath = path.join(root, "shrinking.log");
+      await writeFile(filePath, Buffer.alloc(300 * 1024, 0x61));
+
+      await expect(
+        streamExplorerFile({ root, relativePath: "shrinking.log" }, async (file) => {
+          await truncate(filePath, 100 * 1024);
+          for await (const _chunk of file.chunks) {
+            // Consume until the stream detects the premature EOF.
+          }
+        }),
+      ).rejects.toThrow("File changed during transfer");
+    } finally {
+      await rm(root, { recursive: true, force: true });
+    }
+  });
+
+  it("fails a stream when the file is overwritten in place", async () => {
+    const root = await createTempDir("paseo-file-stream-overwrite-");
+
+    try {
+      const filePath = path.join(root, "changing.log");
+      const initial = Buffer.alloc(600 * 1024, 0x61);
+      await writeFile(filePath, initial);
+
+      await expect(
+        streamExplorerFile({ root, relativePath: "changing.log" }, async (file) => {
+          let chunkIndex = 0;
+          for await (const _chunk of file.chunks) {
+            chunkIndex += 1;
+            if (chunkIndex === 1) {
+              const replacement = Buffer.alloc(initial.byteLength, 0x62);
+              await writeFile(filePath, replacement);
+            }
+          }
+        }),
+      ).rejects.toThrow("File changed during transfer");
+    } finally {
+      await rm(root, { recursive: true, force: true });
+    }
+  });
+
+  it("classifies sampled text when UTF-8 crosses the sample boundary", async () => {
+    const root = await createTempDir("paseo-file-stream-utf8-");
+
+    try {
+      const content = Buffer.concat([Buffer.alloc(8191, 0x61), Buffer.from("€"), Buffer.from("z")]);
+      await writeFile(path.join(root, "sample.txt"), content);
+      let kind: string | undefined;
+      let encoding: string | undefined;
+
+      await streamExplorerFile({ root, relativePath: "sample.txt" }, async (file) => {
+        kind = file.kind;
+        encoding = file.encoding;
+      });
+
+      expect(kind).toBe("text");
+      expect(encoding).toBe("utf-8");
+    } finally {
+      await rm(root, { recursive: true, force: true });
+    }
+  });
+
+  it("rejects incomplete UTF-8 when the whole file was sampled", async () => {
+    const root = await createTempDir("paseo-file-stream-invalid-utf8-");
+
+    try {
+      await writeFile(path.join(root, "invalid.txt"), Buffer.from([0x61, 0xe2, 0x82]));
+      let kind: string | undefined;
+
+      await streamExplorerFile({ root, relativePath: "invalid.txt" }, async (file) => {
+        kind = file.kind;
+      });
+
+      expect(kind).toBe("binary");
+    } finally {
+      await rm(root, { recursive: true, force: true });
+    }
+  });
+
+  it("detects binary bytes beyond the initial classification block", async () => {
+    const root = await createTempDir("paseo-file-stream-late-binary-");
+
+    try {
+      const content = Buffer.concat([Buffer.alloc(8192, 0x61), Buffer.from([0xff])]);
+      await writeFile(path.join(root, "late-binary.unknown"), content);
+      let kind: string | undefined;
+
+      await streamExplorerFile({ root, relativePath: "late-binary.unknown" }, async (file) => {
+        kind = file.kind;
+      });
+
+      expect(kind).toBe("binary");
+    } finally {
+      await rm(root, { recursive: true, force: true });
+    }
+  });
+
   it("expands a ~ prefix in relative paths against the user home directory", async () => {
     const root = await createHomeTempDir(".paseo-file-explorer-home-");
 
diff --git a/packages/server/src/server/file-explorer/service.ts b/packages/server/src/server/file-explorer/service.ts
index 45a8d74ca..a33007b59 100644
--- a/packages/server/src/server/file-explorer/service.ts
+++ b/packages/server/src/server/file-explorer/service.ts
@@ -76,12 +76,24 @@ export interface FileExplorerFileBytes {
   revision: string;
 }
 
+export interface FileExplorerFileStream {
+  path: string;
+  kind: ExplorerFileKind;
+  encoding: "utf-8" | "binary";
+  mimeType: string;
+  size: number;
+  modifiedAt: string;
+  revision: string;
+  chunks: AsyncIterable<Uint8Array>;
+}
+
 const TEXT_MIME_TYPES: Record<string, string> = {
   ".json": "application/json",
 };
 
 const DEFAULT_TEXT_MIME_TYPE = "text/plain";
 const FILE_TYPE_SAMPLE_BYTES = 8192;
+export const FILE_EXPLORER_STREAM_CHUNK_BYTES = 256 * 1024;
 export const MAX_EDITABLE_FILE_BYTES = 1024 * 1024;
 const READ_FILE_OPEN_FLAGS =
   process.platform === "win32" ? constants.O_RDONLY : constants.O_RDONLY | constants.O_NOFOLLOW;
@@ -275,6 +287,109 @@ export async function readExplorerFileBytes({
   }
 }
 
+export async function streamExplorerFile(
+  { root, relativePath }: ReadFileParams,
+  consume: (file: FileExplorerFileStream) => Promise<void>,
+): Promise<void> {
+  const filePath = await resolveScopedPath({ root, relativePath });
+  const handle = await openFileForRead(filePath.resolvedPath);
+
+  try {
+    const stats = await handle.stat({ bigint: true });
+    if (!stats.isFile()) {
+      throw new Error("Requested path is not a file");
+    }
+
+    const advertisedSize = Number(stats.size);
+    const advertisedRevision = fileRevision(stats);
+    const ext = path.extname(filePath.resolvedPath).toLowerCase();
+    const isImage = ext in IMAGE_MIME_TYPES;
+    const isBinary = isImage || (await isFileHandleBinary(handle, advertisedSize));
+    let kind: ExplorerFileKind = "text";
+    let mimeType = textMimeTypeForExtension(ext);
+    if (isImage) {
+      kind = "image";
+      mimeType = IMAGE_MIME_TYPES[ext];
+    } else if (isBinary) {
+      kind = "binary";
+      mimeType = "application/octet-stream";
+    }
+
+    await consume({
+      path: normalizeRelativePath({ root, targetPath: filePath.requestedPath }),
+      kind,
+      encoding: isBinary ? "binary" : "utf-8",
+      mimeType,
+      size: advertisedSize,
+      modifiedAt: stats.mtime.toISOString(),
+      revision: advertisedRevision,
+      chunks: readFileHandleChunks(handle, advertisedSize, advertisedRevision),
+    });
+  } finally {
+    await handle.close();
+  }
+}
+
+async function isFileHandleBinary(handle: FileHandle, advertisedSize: number): Promise<boolean> {
+  if (advertisedSize === 0) return false;
+
+  const decoder = new TextDecoder("utf-8", { fatal: true });
+  let position = 0;
+  let suspiciousBytes = 0;
+  while (position < advertisedSize) {
+    const block = Buffer.allocUnsafe(
+      Math.min(FILE_EXPLORER_STREAM_CHUNK_BYTES, advertisedSize - position),
+    );
+    const { bytesRead } = await handle.read(block, 0, block.byteLength, position);
+    if (bytesRead === 0) {
+      throw new Error("File changed during transfer");
+    }
+    const bytes = block.subarray(0, bytesRead);
+    for (const byte of bytes) {
+      if (byte === 0) return true;
+      const isControl = byte < 32 && byte !== 9 && byte !== 10 && byte !== 13;
+      if (isControl || byte === 127) suspiciousBytes += 1;
+    }
+    try {
+      decoder.decode(bytes, { stream: true });
+    } catch {
+      return true;
+    }
+    position += bytesRead;
+  }
+
+  try {
+    decoder.decode();
+  } catch {
+    return true;
+  }
+  return suspiciousBytes / advertisedSize > 0.3;
+}
+
+async function* readFileHandleChunks(
+  handle: FileHandle,
+  advertisedSize: number,
+  advertisedRevision: string,
+): AsyncIterable<Uint8Array> {
+  let position = 0;
+  while (position < advertisedSize) {
+    const chunk = Buffer.allocUnsafe(
+      Math.min(FILE_EXPLORER_STREAM_CHUNK_BYTES, advertisedSize - position),
+    );
+    const { bytesRead } = await handle.read(chunk, 0, chunk.byteLength, position);
+    if (bytesRead === 0) {
+      throw new Error("File changed during transfer");
+    }
+    position += bytesRead;
+    yield chunk.subarray(0, bytesRead);
+  }
+
+  const finalStats = await handle.stat({ bigint: true });
+  if (fileRevision(finalStats) !== advertisedRevision) {
+    throw new Error("File changed during transfer");
+  }
+}
+
 export async function getExplorerFileVersion({
   root,
   relativePath,
diff --git a/packages/server/src/server/relay-transport.test.ts b/packages/server/src/server/relay-transport.test.ts
index fb1ddfe4b..06775e5c5 100644
--- a/packages/server/src/server/relay-transport.test.ts
+++ b/packages/server/src/server/relay-transport.test.ts
@@ -1,5 +1,7 @@
 import { afterEach, beforeEach, describe, expect, test, vi } from "vitest";
 import type pino from "pino";
+import { createClientChannel, type Transport } from "@getpaseo/relay/e2ee";
+import { exportPublicKey, generateKeyPair } from "@getpaseo/relay";
 import { startRelayTransport } from "./relay-transport";
 
 function createMockLogger() {
@@ -32,7 +34,10 @@ class FakeRelayWebSocket {
   sent: Array<string | Uint8Array | ArrayBuffer> = [];
   terminateCalls = 0;
   pingCalls = 0;
+  deferSendCompletion = false;
+  onSend: ((data: string | Uint8Array | ArrayBuffer) => void) | null = null;
   private readonly listeners = new Map<string, Array<(...args: unknown[]) => void>>();
+  private readonly pendingSendCallbacks: Array<(error?: Error) => void> = [];
 
   constructor(readonly url: string) {}
 
@@ -61,11 +66,22 @@ class FakeRelayWebSocket {
     this.emit("close", 1006, "");
   }
 
-  send(data: string | Uint8Array | ArrayBuffer) {
+  send(data: string | Uint8Array | ArrayBuffer, callback?: (error?: Error) => void) {
     if (this.readyState !== FakeRelayWebSocket.OPEN) {
       throw new Error(`WebSocket not open (readyState=${this.readyState})`);
     }
     this.sent.push(data);
+    this.onSend?.(data);
+    if (!callback) return;
+    if (this.deferSendCompletion) {
+      this.pendingSendCallbacks.push(callback);
+      return;
+    }
+    callback();
+  }
+
+  completeNextSend() {
+    this.pendingSendCallbacks.shift()?.();
   }
 
   ping() {
@@ -80,8 +96,8 @@ class FakeRelayWebSocket {
     this.emit("open");
   }
 
-  message(data: unknown) {
-    this.emit("message", data);
+  message(data: unknown, isBinary = data instanceof ArrayBuffer || ArrayBuffer.isView(data)) {
+    this.emit("message", data, isBinary);
   }
 
   pong() {
@@ -239,6 +255,80 @@ describe("relay-transport control lifecycle", () => {
     ]);
   });
 
+  test("encrypted sends wait for the physical data socket callback", async () => {
+    const logger = createMockLogger();
+    const daemonKeyPair = generateKeyPair();
+    let resolveAttached: ((socket: unknown) => void) | undefined;
+    const attached = new Promise<unknown>((resolve) => {
+      resolveAttached = resolve;
+    });
+    const controller = startRelayTransport({
+      logger: logger as unknown as pino.Logger,
+      attachSocket: async (socket) => resolveAttached?.(socket),
+      relayEndpoint: "relay.paseo.sh:443",
+      relayUseTls: true,
+      serverId: "srv_test",
+      daemonKeyPair,
+      createWebSocket: relay.createWebSocket,
+    });
+    controllers.push(controller);
+
+    const control = relay.sockets[0];
+    control.open();
+    control.message(JSON.stringify({ type: "sync", connectionIds: [] }), false);
+    control.message(JSON.stringify({ type: "connected", connectionId: "clt_test" }), false);
+
+    const dataSocket = relay.sockets[1];
+    dataSocket.deferSendCompletion = true;
+    dataSocket.open();
+    let clientTransport: Transport;
+    clientTransport = {
+      send: (data) => dataSocket.message(data, data instanceof ArrayBuffer),
+      close: () => undefined,
+      onmessage: null,
+      onclose: null,
+      onerror: null,
+    };
+    dataSocket.onSend = (data) => {
+      clientTransport.onmessage?.({
+        data: data instanceof Uint8Array ? data.slice().buffer : data,
+        isBinary: data instanceof ArrayBuffer || data instanceof Uint8Array,
+      });
+    };
+    let resolveClientOpen: (() => void) | undefined;
+    const clientOpen = new Promise<void>((resolve) => {
+      resolveClientOpen = resolve;
+    });
+    await createClientChannel(clientTransport, exportPublicKey(daemonKeyPair.publicKey), {
+      onopen: () => resolveClientOpen?.(),
+    });
+
+    let attachedCompleted = false;
+    void attached.then(() => {
+      attachedCompleted = true;
+      return undefined;
+    });
+    await clientOpen;
+    await Promise.resolve();
+    expect(attachedCompleted).toBe(false);
+    dataSocket.completeNextSend();
+    const encryptedSocket = (await attached) as {
+      send: (data: Uint8Array) => void | Promise<void>;
+    };
+    let completed = false;
+
+    const sending = Promise.resolve(encryptedSocket.send(new Uint8Array([1, 2, 3]))).then(() => {
+      completed = true;
+      return undefined;
+    });
+    await Promise.resolve();
+    expect(completed).toBe(false);
+
+    dataSocket.completeNextSend();
+    await sending;
+    expect(completed).toBe(true);
+  });
+
   test("uses relayUseTls for control and data socket URLs", () => {
     const logger = createMockLogger();
     const controller = startRelayTransport({
diff --git a/packages/server/src/server/relay-transport.ts b/packages/server/src/server/relay-transport.ts
index b39fef1a2..b60b01bd0 100644
--- a/packages/server/src/server/relay-transport.ts
+++ b/packages/server/src/server/relay-transport.ts
@@ -28,7 +28,7 @@ export interface RelayTransportController {
 interface RelaySocketLike {
   readyState: number;
   bufferedAmount?: number;
-  send: (data: string | Uint8Array | ArrayBuffer) => void;
+  send: (data: string | Uint8Array | ArrayBuffer, callback?: (error?: Error) => void) => void;
   close: (code?: number, reason?: string) => void;
   terminate?: () => void;
   on: (event: "message" | "close" | "error", listener: (...args: unknown[]) => void) => void;
@@ -467,16 +467,23 @@ function createRelayTransportAdapter(
   logger: pino.Logger,
 ): RelayTransport {
   const relayTransport: RelayTransport = {
-    send: (data) => {
-      try {
-        socket.send(data);
-      } catch (err) {
-        // Socket likely transitioned to closed between checks; let onclose/onerror
-        // drive cleanup. Without this guard the synchronous throw would propagate
-        // up as an uncaughtException and take down the daemon.
-        logger.warn({ err }, "relay_socket_send_failed");
-      }
-    },
+    send: (data) =>
+      new Promise<void>((resolve, reject) => {
+        try {
+          socket.send(data, (error) => {
+            if (!error) {
+              resolve();
+              return;
+            }
+            logger.warn({ err: error }, "relay_socket_send_failed");
+            reject(error);
+          });
+        } catch (error) {
+          const err = error instanceof Error ? error : new Error(String(error));
+          logger.warn({ err }, "relay_socket_send_failed");
+          reject(err);
+        }
+      }),
     close: (code?: number, reason?: string) => socket.close(code, reason),
     onmessage: null,
     onclose: null,
diff --git a/packages/server/src/server/session.ts b/packages/server/src/server/session.ts
index 04f04fe6f..7cf2f24c3 100644
--- a/packages/server/src/server/session.ts
+++ b/packages/server/src/server/session.ts
@@ -405,6 +405,7 @@ export interface SessionOptions {
   onMessage: (msg: SessionOutboundMessage) => void;
   onMessageToSource?: (source: object, msg: SessionOutboundMessage) => void;
   onBinaryMessage?: (frame: Uint8Array) => void;
+  onBinaryMessageToSource?: (source: object, frame: Uint8Array) => Promise<void>;
   getTransportBufferedAmount?: () => number | null;
   onLifecycleIntent?: (intent: SessionLifecycleIntent) => void;
   onWorkspaceRecovered?: (workspace: PersistedWorkspaceRecord) => Promise<void>;
@@ -568,6 +569,9 @@ export class Session {
     | ((source: object, msg: SessionOutboundMessage) => void)
     | null;
   private readonly onBinaryMessage: ((frame: Uint8Array) => void) | null;
+  private readonly onBinaryMessageToSource:
+    | ((source: object, frame: Uint8Array) => Promise<void>)
+    | null;
   private readonly getTransportBufferedAmount: () => number | null;
   private readonly onLifecycleIntent: ((intent: SessionLifecycleIntent) => void) | null;
   private readonly onWorkspaceRecovered:
@@ -646,6 +650,7 @@ export class Session {
       onMessage,
       onMessageToSource,
       onBinaryMessage,
+      onBinaryMessageToSource,
       getTransportBufferedAmount,
       onLifecycleIntent,
       onWorkspaceRecovered,
@@ -698,6 +703,7 @@ export class Session {
     this.onMessage = onMessage;
     this.onMessageToSource = onMessageToSource ?? null;
     this.onBinaryMessage = onBinaryMessage ?? null;
+    this.onBinaryMessageToSource = onBinaryMessageToSource ?? null;
     this.getTransportBufferedAmount = getTransportBufferedAmount ?? (() => 0);
     this.onLifecycleIntent = onLifecycleIntent ?? null;
     this.onWorkspaceRecovered = onWorkspaceRecovered ?? null;
@@ -711,8 +717,8 @@ export class Session {
     });
     this.workspaceFilesSession = new WorkspaceFilesSession({
       host: {
-        emit: (msg) => this.emit(msg),
-        emitBinary: (frame) => this.emitBinary(frame),
+        emit: (msg, source) => this.emitForSource(msg, source),
+        emitBinary: (frame, source) => this.emitBinaryForFileTransfer(frame, source),
         hasBinaryChannel: () => this.onBinaryMessage !== null,
       },
       downloadTokenStore,
@@ -1786,7 +1792,7 @@ export class Session {
       this.dispatchCheckoutMessage(msg) ??
       this.dispatchWorkspaceRecoveryMessage(msg) ??
       this.dispatchWorkspaceAndProjectMessage(msg) ??
-      this.dispatchWorkspaceFileMessage(msg) ??
+      this.dispatchWorkspaceFileMessage(msg, source) ??
       this.dispatchProviderMessage(msg) ??
       this.dispatchTerminalMessage(msg) ??
       this.dispatchChatScheduleLoopMessage(msg) ??
@@ -2106,10 +2112,13 @@ export class Session {
     }
   }
 
-  private dispatchWorkspaceFileMessage(msg: SessionInboundMessage): Promise<void> | undefined {
+  private dispatchWorkspaceFileMessage(
+    msg: SessionInboundMessage,
+    source?: object,
+  ): Promise<void> | undefined {
     switch (msg.type) {
       case "file_explorer_request":
-        return this.workspaceFilesSession.handleFileExplorerRequest(msg);
+        return this.workspaceFilesSession.handleFileExplorerRequest(msg, source);
       case "fs.file.subscribe.request":
         return this.workspaceFilesSession.handleFileSubscribeRequest(msg);
       case "fs.file.unsubscribe.request":
@@ -6532,6 +6541,22 @@ export class Session {
     }
   }
 
+  private async emitBinaryForFileTransfer(frame: Uint8Array, source?: object): Promise<void> {
+    if (source && this.onBinaryMessageToSource) {
+      await this.onBinaryMessageToSource(source, frame);
+      return;
+    }
+    this.emitBinary(frame);
+  }
+
+  private emitForSource(msg: SessionOutboundMessage, source?: object): void {
+    if (source && this.onMessageToSource) {
+      this.onMessageToSource(source, msg);
+      return;
+    }
+    this.emit(msg);
+  }
+
   /**
    * Clean up session resources
    */
diff --git a/packages/server/src/server/session/files/workspace-files-session.test.ts b/packages/server/src/server/session/files/workspace-files-session.test.ts
index cfc45c5c7..0b09c8774 100644
--- a/packages/server/src/server/session/files/workspace-files-session.test.ts
+++ b/packages/server/src/server/session/files/workspace-files-session.test.ts
@@ -30,13 +30,21 @@ function makeDir(prefix: string): string {
   return dir;
 }
 
-function makeSubsystem(options: { hasBinaryChannel?: boolean } = {}) {
+function makeSubsystem(
+  options: {
+    hasBinaryChannel?: boolean;
+    emitBinary?: (frame: Uint8Array) => Promise<void> | void;
+  } = {},
+) {
   const emitted: SessionOutboundMessage[] = [];
   const binary: Uint8Array[] = [];
   let hasBinary = options.hasBinaryChannel ?? false;
   const host: WorkspaceFilesSessionHost = {
     emit: (msg) => emitted.push(msg),
-    emitBinary: (frame) => binary.push(frame),
+    emitBinary: async (frame) => {
+      binary.push(frame);
+      await options.emitBinary?.(frame);
+    },
     hasBinaryChannel: () => hasBinary,
   };
   const paseoHome = makeDir("workspace-files-home-");
@@ -136,6 +144,74 @@ describe("WorkspaceFilesSession", () => {
     ]);
   });
 
+  test("streams a real file larger than the socket limit as paced ordered chunks", async () => {
+    const cwd = makeDir("workspace-files-large-binary-");
+    const fileBytes = Buffer.alloc(8 * 1024 * 1024 + 123);
+    for (let index = 0; index < fileBytes.length; index += 1) {
+      fileBytes[index] = index % 251;
+    }
+    writeFileSync(join(cwd, "large.bin"), fileBytes);
+
+    let releaseFirstChunk: (() => void) | undefined;
+    const firstChunkSent = new Promise<void>((resolve) => {
+      releaseFirstChunk = resolve;
+    });
+    let chunkSends = 0;
+    const { subsystem, emitted, binary } = makeSubsystem({
+      hasBinaryChannel: true,
+      emitBinary: async (frame) => {
+        if (decodeFileTransferFrame(frame)?.opcode !== FileTransferOpcode.FileChunk) return;
+        chunkSends += 1;
+        if (chunkSends === 1) await firstChunkSent;
+      },
+    });
+
+    const transfer = subsystem.handleFileExplorerRequest({
+      type: "file_explorer_request",
+      cwd,
+      path: "large.bin",
+      mode: "file",
+      requestId: "req-large-binary",
+      acceptBinary: true,
+    });
+
+    await expect.poll(() => chunkSends).toBe(1);
+    expect(binary.map((frame) => decodeFileTransferFrame(frame)?.opcode)).toEqual([
+      FileTransferOpcode.FileBegin,
+      FileTransferOpcode.FileChunk,
+    ]);
+
+    await subsystem.handleFileExplorerRequest({
+      type: "file_explorer_request",
+      cwd,
+      path: ".",
+      mode: "list",
+      requestId: "req-unrelated-list",
+    });
+    expect(emitted).toEqual([
+      expect.objectContaining({
+        type: "file_explorer_response",
+        payload: expect.objectContaining({ requestId: "req-unrelated-list", error: null }),
+      }),
+    ]);
+
+    releaseFirstChunk?.();
+    await transfer;
+
+    const frames = binary.map((frame) => decodeFileTransferFrame(frame));
+    const chunks = frames.flatMap((frame) =>
+      frame?.opcode === FileTransferOpcode.FileChunk ? [frame.payload] : [],
+    );
+    expect(chunks.length).toBeGreaterThan(1);
+    expect(chunks.every((chunk) => chunk.byteLength <= 256 * 1024)).toBe(true);
+    expect(
+      Buffer.compare(Buffer.concat(chunks.map((chunk) => Buffer.from(chunk))), fileBytes),
+    ).toBe(0);
+    expect(frames.at(0)?.opcode).toBe(FileTransferOpcode.FileBegin);
+    expect(frames.at(-1)?.opcode).toBe(FileTransferOpcode.FileEnd);
+    expect(emitted).toHaveLength(1);
+  }, 30_000);
+
   test("rejects an empty file-explorer cwd with an error envelope", async () => {
     const { subsystem, emitted } = makeSubsystem();
 
diff --git a/packages/server/src/server/session/files/workspace-files-session.ts b/packages/server/src/server/session/files/workspace-files-session.ts
index 740f74a61..dd7d7d04d 100644
--- a/packages/server/src/server/session/files/workspace-files-session.ts
+++ b/packages/server/src/server/session/files/workspace-files-session.ts
@@ -21,7 +21,7 @@ import {
   getDownloadableFileInfo,
   listDirectoryEntries,
   readExplorerFile,
-  readExplorerFileBytes,
+  streamExplorerFile,
   writeExplorerFile,
 } from "../../file-explorer/service.js";
 import { workspaceFileObserver, type FileObserver } from "../../file-explorer/observer.js";
@@ -34,8 +34,8 @@ import { getProjectIcon } from "../../../utils/project-icon.js";
  * — old clients without a binary channel fall back to inline JSON file content.
  */
 export interface WorkspaceFilesSessionHost {
-  emit(msg: SessionOutboundMessage): void;
-  emitBinary(frame: Uint8Array): void;
+  emit(msg: SessionOutboundMessage, source?: object): void;
+  emitBinary(frame: Uint8Array, source?: object): Promise<void>;
   hasBinaryChannel(): boolean;
 }
 
@@ -136,22 +136,25 @@ export class WorkspaceFilesSession {
     this.fileSubscriptions.clear();
   }
 
-  async handleFileExplorerRequest(request: FileExplorerRequest): Promise<void> {
+  async handleFileExplorerRequest(request: FileExplorerRequest, source?: object): Promise<void> {
     const { cwd: workspaceCwd, path: requestedPath = ".", mode, requestId } = request;
     const cwd = workspaceCwd.trim();
     if (!cwd) {
-      this.host.emit({
-        type: "file_explorer_response",
-        payload: {
-          cwd: workspaceCwd,
-          path: requestedPath,
-          mode,
-          directory: null,
-          file: null,
-          error: "cwd is required",
-          requestId,
+      this.host.emit(
+        {
+          type: "file_explorer_response",
+          payload: {
+            cwd: workspaceCwd,
+            path: requestedPath,
+            mode,
+            directory: null,
+            file: null,
+            error: "cwd is required",
+            requestId,
+          },
         },
-      });
+        source,
+      );
       return;
     }
 
@@ -162,69 +165,77 @@ export class WorkspaceFilesSession {
           relativePath: requestedPath,
         });
 
-        this.host.emit({
-          type: "file_explorer_response",
-          payload: {
-            cwd,
-            path: directory.path,
-            mode,
-            directory,
-            file: null,
-            error: null,
-            requestId,
+        this.host.emit(
+          {
+            type: "file_explorer_response",
+            payload: {
+              cwd,
+              path: directory.path,
+              mode,
+              directory,
+              file: null,
+              error: null,
+              requestId,
+            },
           },
-        });
+          source,
+        );
       } else {
         if (request.acceptBinary && this.host.hasBinaryChannel()) {
-          const file = await readExplorerFileBytes({
-            root: cwd,
-            relativePath: requestedPath,
+          await streamExplorerFile({ root: cwd, relativePath: requestedPath }, async (file) => {
+            await this.host.emitBinary(
+              encodeFileTransferFrame({
+                opcode: FileTransferOpcode.FileBegin,
+                requestId,
+                metadata: {
+                  mime: file.mimeType,
+                  size: file.size,
+                  encoding: file.encoding,
+                  modifiedAt: file.modifiedAt,
+                  revision: file.revision,
+                },
+              }),
+              source,
+            );
+            for await (const chunk of file.chunks) {
+              await this.host.emitBinary(
+                encodeFileTransferFrame({
+                  opcode: FileTransferOpcode.FileChunk,
+                  requestId,
+                  payload: chunk,
+                }),
+                source,
+              );
+            }
+            await this.host.emitBinary(
+              encodeFileTransferFrame({
+                opcode: FileTransferOpcode.FileEnd,
+                requestId,
+              }),
+              source,
+            );
           });
-
-          this.host.emitBinary(
-            encodeFileTransferFrame({
-              opcode: FileTransferOpcode.FileBegin,
-              requestId,
-              metadata: {
-                mime: file.mimeType,
-                size: file.size,
-                encoding: file.encoding,
-                modifiedAt: file.modifiedAt,
-                revision: file.revision,
-              },
-            }),
-          );
-          this.host.emitBinary(
-            encodeFileTransferFrame({
-              opcode: FileTransferOpcode.FileChunk,
-              requestId,
-              payload: file.bytes,
-            }),
-          );
-          this.host.emitBinary(
-            encodeFileTransferFrame({
-              opcode: FileTransferOpcode.FileEnd,
-              requestId,
-            }),
-          );
         } else {
           const file = await readExplorerFile({
             root: cwd,
             relativePath: requestedPath,
           });
 
-          this.host.emit({
-            type: "file_explorer_response",
-            payload: {
-              cwd,
-              path: file.path,
-              mode,
-              directory: null,
-              file,
-              error: null,
-              requestId,
+          this.host.emit(
+            {
+              type: "file_explorer_response",
+              payload: {
+                cwd,
+                path: file.path,
+                mode,
+                directory: null,
+                file,
+                error: null,
+                requestId,
+              },
             },
-          });
+            source,
+          );
         }
       }
     } catch (error) {
@@ -232,18 +243,21 @@ export class WorkspaceFilesSession {
         { err: error, cwd, path: requestedPath },
         `Failed to fulfill file explorer request for workspace ${cwd}`,
       );
-      this.host.emit({
-        type: "file_explorer_response",
-        payload: {
-          cwd,
-          path: requestedPath,
-          mode,
-          directory: null,
-          file: null,
-          error: getErrorMessage(error),
-          requestId,
+      this.host.emit(
+        {
+          type: "file_explorer_response",
+          payload: {
+            cwd,
+            path: requestedPath,
+            mode,
+            directory: null,
+            file: null,
+            error: getErrorMessage(error),
+            requestId,
+          },
         },
-      });
+        source,
+      );
     }
   }
 
diff --git a/packages/server/src/server/websocket-server.file-transfer.e2e.test.ts b/packages/server/src/server/websocket-server.file-transfer.e2e.test.ts
new file mode 100644
index 000000000..5131456ee
--- /dev/null
+++ b/packages/server/src/server/websocket-server.file-transfer.e2e.test.ts
@@ -0,0 +1,168 @@
+import { mkdtempSync, rmSync, writeFileSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { afterEach, expect, test } from "vitest";
+import { WebSocket, type RawData } from "ws";
+import {
+  decodeFileTransferFrame,
+  FileTransferOpcode,
+} from "@getpaseo/protocol/binary-frames/index";
+import { createTestPaseoDaemon, type TestPaseoDaemon } from "./test-utils/index.js";
+import { WSOutboundMessageSchema, type WSOutboundMessage } from "./messages.js";
+
+const TEST_TIMEOUT_MS = 30_000;
+const FILE_SIZE = 8 * 1024 * 1024 + 123;
+
+let daemon: TestPaseoDaemon | undefined;
+const temporaryDirectories: string[] = [];
+const sockets: WebSocket[] = [];
+
+afterEach(async () => {
+  for (const socket of sockets.splice(0)) socket.terminate();
+  await daemon?.close();
+  daemon = undefined;
+  for (const directory of temporaryDirectories.splice(0)) {
+    rmSync(directory, { recursive: true, force: true });
+  }
+});
+
+test(
+  "a large file stays ordered, source-scoped, and does not block another socket",
+  async () => {
+    const cwd = mkdtempSync(join(tmpdir(), "paseo-large-file-transfer-"));
+    temporaryDirectories.push(cwd);
+    const expected = Buffer.alloc(FILE_SIZE);
+    for (let index = 0; index < expected.length; index += 1) expected[index] = index % 251;
+    writeFileSync(join(cwd, "large.bin"), expected);
+
+    daemon = await createTestPaseoDaemon();
+    const source = await connectSocket(daemon.port, "shared-file-client");
+    const unrelated = await connectSocket(daemon.port, "shared-file-client");
+    sockets.push(source, unrelated);
+
+    let unrelatedBinaryFrames = 0;
+    unrelated.on("message", (_data, isBinary) => {
+      if (isBinary) unrelatedBinaryFrames += 1;
+    });
+
+    const transfer = receiveFileTransfer(source, "req-large-file");
+    source.send(
+      JSON.stringify({
+        type: "session",
+        message: {
+          type: "file_explorer_request",
+          cwd,
+          path: "large.bin",
+          mode: "file",
+          acceptBinary: true,
+          requestId: "req-large-file",
+        },
+      }),
+    );
+
+    await sendAndWait(
+      unrelated,
+      {
+        type: "session",
+        message: { type: "ping", requestId: "req-unrelated", clientSentAt: 1 },
+      },
+      (message) =>
+        message.type === "session" &&
+        message.message.type === "pong" &&
+        message.message.payload.requestId === "req-unrelated",
+    );
+
+    const frames = await transfer;
+    const chunks = frames.flatMap((frame) =>
+      frame.opcode === FileTransferOpcode.FileChunk ? [frame.payload] : [],
+    );
+    expect(frames[0]?.opcode).toBe(FileTransferOpcode.FileBegin);
+    expect(frames.at(-1)?.opcode).toBe(FileTransferOpcode.FileEnd);
+    expect(chunks.length).toBeGreaterThan(1);
+    expect(chunks.every((chunk) => chunk.byteLength <= 256 * 1024)).toBe(true);
+    expect(Buffer.compare(Buffer.concat(chunks.map((chunk) => Buffer.from(chunk))), expected)).toBe(
+      0,
+    );
+    expect(source.readyState).toBe(WebSocket.OPEN);
+    expect(unrelated.readyState).toBe(WebSocket.OPEN);
+    expect(unrelatedBinaryFrames).toBe(0);
+  },
+  TEST_TIMEOUT_MS,
+);
+
+async function connectSocket(port: number, clientId: string): Promise<WebSocket> {
+  const socket = new WebSocket(`ws://127.0.0.1:${port}/ws`);
+  await new Promise<void>((resolve, reject) => {
+    socket.once("open", resolve);
+    socket.once("error", reject);
+  });
+  await sendAndWait(
+    socket,
+    { type: "hello", clientId, clientType: "browser", protocolVersion: 1 },
+    (message) =>
+      message.type === "session" &&
+      message.message.type === "status" &&
+      message.message.payload.status === "server_info",
+  );
+  return socket;
+}
+
+function receiveFileTransfer(source: WebSocket, requestId: string) {
+  return new Promise<NonNullable<ReturnType<typeof decodeFileTransferFrame>>[]>(
+    (resolve, reject) => {
+      const frames: NonNullable<ReturnType<typeof decodeFileTransferFrame>>[] = [];
+      const timeout = setTimeout(() => {
+        cleanup();
+        reject(new Error("Timed out waiting for file transfer"));
+      }, TEST_TIMEOUT_MS);
+      const onMessage = (data: RawData, isBinary: boolean) => {
+        if (!isBinary) return;
+        const frame = decodeFileTransferFrame(new Uint8Array(data as Buffer));
+        if (!frame || frame.requestId !== requestId) return;
+        frames.push(frame);
+        if (frame.opcode === FileTransferOpcode.FileEnd) {
+          cleanup();
+          resolve(frames);
+        }
+      };
+      const onClose = () => {
+        cleanup();
+        reject(new Error("Socket closed during file transfer"));
+      };
+      const cleanup = () => {
+        clearTimeout(timeout);
+        source.off("message", onMessage);
+        source.off("close", onClose);
+      };
+      source.on("message", onMessage);
+      source.on("close", onClose);
+    },
+  );
+}
+
+function sendAndWait(
+  socket: WebSocket,
+  message: unknown,
+  matches: (message: WSOutboundMessage) => boolean,
+): Promise<WSOutboundMessage> {
+  const response = new Promise<WSOutboundMessage>((resolve, reject) => {
+    const timeout = setTimeout(() => {
+      cleanup();
+      reject(new Error("Timed out waiting for WebSocket message"));
+    }, TEST_TIMEOUT_MS);
+    const onMessage = (data: RawData, isBinary: boolean) => {
+      if (isBinary) return;
+      const parsed = WSOutboundMessageSchema.safeParse(JSON.parse(data.toString()));
+      if (!parsed.success || !matches(parsed.data)) return;
+      cleanup();
+      resolve(parsed.data);
+    };
+    const cleanup = () => {
+      clearTimeout(timeout);
+      socket.off("message", onMessage);
+    };
+    socket.on("message", onMessage);
+  });
+  socket.send(JSON.stringify(message));
+  return response;
+}
diff --git a/packages/server/src/server/websocket-server.ts b/packages/server/src/server/websocket-server.ts
index 104eb08e9..c54c4c5fc 100644
--- a/packages/server/src/server/websocket-server.ts
+++ b/packages/server/src/server/websocket-server.ts
@@ -96,6 +96,7 @@ import {
   outboundFrameByteLength,
   physicalSocketHasCapacity,
   sendBoundedPhysicalFrame,
+  sendBoundedPhysicalFrameAndWait,
 } from "./websocket/physical-socket.js";
 
 const WS_CLOSE_DAEMON_AUTH_FAILED = 4401;
@@ -371,7 +372,10 @@ function getBrowserHostCapability(
 export interface WebSocketLike {
   readyState: number;
   bufferedAmount?: number;
-  send: (data: string | Uint8Array | ArrayBuffer) => void;
+  send: (
+    data: string | Uint8Array | ArrayBuffer,
+    callback?: (error?: Error) => void,
+  ) => void | Promise<void>;
   close: (code?: number, reason?: string) => void;
   terminate?: () => void;
   on: (event: "message" | "close" | "error", listener: (...args: unknown[]) => void) => void;
@@ -423,6 +427,7 @@ interface SocketSessionOptions {
   onMessage: (message: SessionOutboundMessage) => void;
   onMessageToSource?: (source: object, message: SessionOutboundMessage) => void;
   onBinaryMessage?: (frame: Uint8Array) => void;
+  onBinaryMessageToSource?: (source: object, frame: Uint8Array) => Promise<void>;
   getTransportBufferedAmount?: () => number | null;
   onLifecycleIntent?: (intent: SessionLifecycleIntent) => void;
   hubExecutionAgents?: HubExecutionAgents;
@@ -1054,6 +1059,23 @@ export class VoiceAssistantWebSocketServer {
     });
   }
 
+  private async sendBinaryToClientAndWait(ws: WebSocketLike, frame: Uint8Array): Promise<void> {
+    try {
+      const sent = await sendBoundedPhysicalFrameAndWait({
+        socket: ws,
+        frame,
+        onHighWater: () => this.closeAtOutboundHighWater(ws),
+      });
+      if (!sent) {
+        throw new Error("Physical WebSocket is not open");
+      }
+      this.runtimeMetrics.recordOutboundBinaryFrame(ws.bufferedAmount);
+    } catch (err) {
+      this.logger.warn({ err }, "ws_send_failed");
+      throw err;
+    }
+  }
+
   private sendFrameToClient(
     ws: WebSocketLike,
     frame: string | Uint8Array,
@@ -1226,6 +1248,12 @@ export class VoiceAssistantWebSocketServer {
         }
         this.sendBinaryToConnection(connection, frame);
       },
+      onBinaryMessageToSource: async (source, frame) => {
+        if (!connection || !connection.sockets.has(source as WebSocketLike)) {
+          throw new Error("File transfer source socket is no longer attached");
+        }
+        await this.sendBinaryToClientAndWait(source as WebSocketLike, frame);
+      },
       getTransportBufferedAmount: () => {
         if (!connection) {
           return null;
@@ -1271,6 +1299,7 @@ export class VoiceAssistantWebSocketServer {
       onMessage: options.onMessage,
       onMessageToSource: options.onMessageToSource,
       onBinaryMessage: options.onBinaryMessage,
+      onBinaryMessageToSource: options.onBinaryMessageToSource,
       getTransportBufferedAmount: options.getTransportBufferedAmount,
       onLifecycleIntent: options.onLifecycleIntent,
       logger: options.connectionLogger.child({ module: "session" }),
diff --git a/packages/server/src/server/websocket/encrypted-relay-socket.test.ts b/packages/server/src/server/websocket/encrypted-relay-socket.test.ts
index 53b230c56..2e50d7530 100644
--- a/packages/server/src/server/websocket/encrypted-relay-socket.test.ts
+++ b/packages/server/src/server/websocket/encrypted-relay-socket.test.ts
@@ -40,10 +40,11 @@ class BlockingChannel implements EncryptedRelayChannel {
 test("negotiated binary ciphertext accepts the exact hard bound and rejects one byte over", async () => {
   const channel = new BlockingChannel();
   let terminations = 0;
+  let transportBufferedAmount = 0;
   const socket = createEncryptedRelaySocket({
     channel,
     emitter: new EventEmitter(),
-    getTransportBufferedAmount: () => 0,
+    getTransportBufferedAmount: () => transportBufferedAmount,
     terminateTransport: () => {
       terminations += 1;
     },
@@ -51,9 +52,11 @@ test("negotiated binary ciphertext accepts the exact hard bound and rejects one
 
   socket.send(new Uint8Array(MAX_PHYSICAL_SOCKET_BUFFERED_BYTES - 40));
   expect(channel.sent).toHaveLength(1);
+  transportBufferedAmount = MAX_PHYSICAL_SOCKET_BUFFERED_BYTES;
   expect(socket.bufferedAmount).toBe(MAX_PHYSICAL_SOCKET_BUFFERED_BYTES);
 
-  socket.send(new Uint8Array(1));
+  const rejected = socket.send(new Uint8Array(1));
+  await expect(rejected).rejects.toThrow("outbound high-water mark");
 
   expect(channel.sent).toHaveLength(1);
   expect(terminations).toBe(1);
@@ -64,7 +67,7 @@ test("negotiated binary ciphertext accepts the exact hard bound and rejects one
   await Promise.resolve();
 });
 
-test("underlying relay backpressure rejects binary before encryption and terminates physically", () => {
+test("underlying relay backpressure rejects binary before encryption and terminates physically", async () => {
   const channel = new BlockingChannel();
   let terminations = 0;
   const socket = createEncryptedRelaySocket({
@@ -76,36 +79,14 @@ test("underlying relay backpressure rejects binary before encryption and termina
     },
   });
 
-  socket.send(new Uint8Array(1));
+  const rejected = socket.send(new Uint8Array(1));
+  await expect(rejected).rejects.toThrow("outbound high-water mark");
 
   expect(channel.sent).toEqual([]);
   expect(channel.closes).toEqual([]);
   expect(terminations).toBe(1);
 });
 
-test("pending encryption and underlying relay backpressure share one hard bound", () => {
-  const channel = new BlockingChannel();
-  let transportBufferedAmount = 3 * 1024 * 1024;
-  let terminations = 0;
-  const socket = createEncryptedRelaySocket({
-    channel,
-    emitter: new EventEmitter(),
-    getTransportBufferedAmount: () => transportBufferedAmount,
-    terminateTransport: () => {
-      terminations += 1;
-    },
-  });
-
-  socket.send(new Uint8Array(3 * 1024 * 1024));
-  expect(channel.sent).toHaveLength(1);
-
-  transportBufferedAmount = 6 * 1024 * 1024;
-  socket.send(new Uint8Array(1));
-
-  expect(channel.sent).toHaveLength(1);
-  expect(terminations).toBe(1);
-});
-
 test("explicit encrypted-socket termination forcibly terminates the relay transport", () => {
   const channel = new BlockingChannel();
   let terminations = 0;
@@ -124,3 +105,42 @@ test("explicit encrypted-socket termination forcibly terminates the relay transp
   expect(channel.closes).toEqual([]);
   expect(socket.readyState).toBe(3);
 });
+
+test("encrypted sends report physical completion through the returned promise", async () => {
+  const channel = new BlockingChannel();
+  const socket = createEncryptedRelaySocket({
+    channel,
+    emitter: new EventEmitter(),
+    getTransportBufferedAmount: () => 0,
+    terminateTransport: () => undefined,
+  });
+  let completed = false;
+
+  const sending = socket.send(new Uint8Array([1]));
+  if (!sending) throw new Error("Expected an awaitable encrypted send");
+  void sending.then(() => (completed = true));
+  await Promise.resolve();
+  expect(completed).toBe(false);
+
+  channel.drain();
+  await sending;
+  expect(completed).toBe(true);
+  expect(socket.bufferedAmount).toBe(0);
+});
+
+test("encrypted sockets do not double-count bytes already buffered by the transport", () => {
+  const channel = new BlockingChannel();
+  let transportBufferedAmount = 0;
+  const socket = createEncryptedRelaySocket({
+    channel,
+    emitter: new EventEmitter(),
+    getTransportBufferedAmount: () => transportBufferedAmount,
+    terminateTransport: () => undefined,
+  });
+  const payload = new Uint8Array(3 * 1024 * 1024);
+
+  void socket.send(payload);
+  transportBufferedAmount = payload.byteLength + 40;
+
+  expect(socket.bufferedAmount).toBe(payload.byteLength + 40);
+});
diff --git a/packages/server/src/server/websocket/encrypted-relay-socket.ts b/packages/server/src/server/websocket/encrypted-relay-socket.ts
index c225ed3ec..3b76a4971 100644
--- a/packages/server/src/server/websocket/encrypted-relay-socket.ts
+++ b/packages/server/src/server/websocket/encrypted-relay-socket.ts
@@ -11,7 +11,7 @@ export interface EncryptedRelayChannel {
 export interface EncryptedRelaySocket {
   readonly readyState: number;
   readonly bufferedAmount: number;
-  send: (data: string | Uint8Array | ArrayBuffer) => void;
+  send: (data: string | Uint8Array | ArrayBuffer) => void | Promise<void>;
   close: (code?: number, reason?: string) => void;
   terminate: () => void;
   on: (event: "message" | "close" | "error", listener: (...args: unknown[]) => void) => void;
@@ -26,7 +26,6 @@ export function createEncryptedRelaySocket(params: {
 }): EncryptedRelaySocket {
   const { channel, emitter, getTransportBufferedAmount, terminateTransport } = params;
   let readyState = 1;
-  let pendingEncryptedBytes = 0;
 
   channel.setState("open");
 
@@ -51,26 +50,25 @@ export function createEncryptedRelaySocket(params: {
       return readyState;
     },
     get bufferedAmount() {
-      return pendingEncryptedBytes + (getTransportBufferedAmount() ?? 0);
+      return getTransportBufferedAmount() ?? 0;
     },
     send: (data) => {
-      if (readyState !== 1) return;
+      if (readyState !== 1) {
+        return Promise.reject(new Error("Encrypted relay socket is not open"));
+      }
       const outbound = normalizeRelaySendPayload(data);
       const outboundBytes = channel.outboundWireByteLength(outbound);
-      const queuedBytes = pendingEncryptedBytes + (getTransportBufferedAmount() ?? 0);
+      const queuedBytes = getTransportBufferedAmount() ?? 0;
       if (queuedBytes + outboundBytes > MAX_PHYSICAL_SOCKET_BUFFERED_BYTES) {
         terminate();
-        return;
+        return Promise.reject(
+          new Error("Encrypted relay socket exceeded its outbound high-water mark"),
+        );
       }
-      pendingEncryptedBytes += outboundBytes;
-      void channel
-        .send(outbound)
-        .catch((error) => {
-          emitter.emit("error", error);
-        })
-        .finally(() => {
-          pendingEncryptedBytes -= outboundBytes;
-        });
+      return channel.send(outbound).catch((error) => {
+        emitter.emit("error", error);
+        throw error;
+      });
     },
     close,
     terminate,
diff --git a/packages/server/src/server/websocket/physical-socket.test.ts b/packages/server/src/server/websocket/physical-socket.test.ts
index 9b334cc11..c81b1410d 100644
--- a/packages/server/src/server/websocket/physical-socket.test.ts
+++ b/packages/server/src/server/websocket/physical-socket.test.ts
@@ -4,6 +4,7 @@ import {
   ApplicationSocketLease,
   MAX_PHYSICAL_SOCKET_BUFFERED_BYTES,
   sendBoundedPhysicalFrame,
+  sendBoundedPhysicalFrameAndWait,
 } from "./physical-socket.js";
 
 test("sockets remain exempt until they send an application ping", () => {
@@ -66,3 +67,56 @@ test("the shared physical send boundary rejects binary above the hard bound", ()
   expect(sent).toEqual([]);
   expect(terminated).toBe(true);
 });
+
+test("the awaitable physical send resolves only when that frame send completes", async () => {
+  const sent: Array<string | Uint8Array | ArrayBuffer> = [];
+  let completeSend: (() => void) | undefined;
+  const socket = {
+    readyState: 1,
+    bufferedAmount: 0,
+    send: (_data: string | Uint8Array | ArrayBuffer, callback?: (error?: Error) => void) => {
+      sent.push(_data);
+      if (callback) completeSend = () => callback();
+    },
+  };
+  let completed = false;
+
+  const sending = sendBoundedPhysicalFrameAndWait({
+    socket,
+    frame: new Uint8Array([1, 2, 3]),
+    onHighWater: () => undefined,
+  }).then(() => {
+    return (completed = true);
+  });
+
+  await Promise.resolve();
+  expect(completed).toBe(false);
+  expect(
+    sendBoundedPhysicalFrame({
+      socket,
+      frame: "unrelated",
+      onHighWater: () => undefined,
+    }),
+  ).toBe(true);
+  expect(sent).toEqual([new Uint8Array([1, 2, 3]), "unrelated"]);
+  completeSend?.();
+  await sending;
+  expect(completed).toBe(true);
+});
+
+test("the awaitable physical send rejects callback errors", async () => {
+  const socket = {
+    readyState: 1,
+    bufferedAmount: 0,
+    send: (_data: string | Uint8Array | ArrayBuffer, callback?: (error?: Error) => void) =>
+      callback?.(new Error("send failed")),
+  };
+
+  await expect(
+    sendBoundedPhysicalFrameAndWait({
+      socket,
+      frame: new Uint8Array([1]),
+      onHighWater: () => undefined,
+    }),
+  ).rejects.toThrow("send failed");
+});
diff --git a/packages/server/src/server/websocket/physical-socket.ts b/packages/server/src/server/websocket/physical-socket.ts
index eed29ae35..491a7c612 100644
--- a/packages/server/src/server/websocket/physical-socket.ts
+++ b/packages/server/src/server/websocket/physical-socket.ts
@@ -50,7 +50,39 @@ export function outboundFrameByteLength(data: string | Uint8Array | ArrayBuffer)
 interface BoundedPhysicalSocket {
   readyState: number;
   bufferedAmount?: number;
-  send: (data: string | Uint8Array | ArrayBuffer) => void;
+  send: (
+    data: string | Uint8Array | ArrayBuffer,
+    callback?: (error?: Error) => void,
+  ) => void | Promise<void>;
+}
+
+export async function sendBoundedPhysicalFrameAndWait(params: {
+  socket: BoundedPhysicalSocket;
+  frame: string | Uint8Array | ArrayBuffer;
+  frameBytes?: number;
+  onHighWater: () => void;
+}): Promise<boolean> {
+  const { socket, frame, frameBytes = outboundFrameByteLength(frame), onHighWater } = params;
+  if (socket.readyState !== 1) return false;
+  if (!physicalSocketHasCapacity(socket, frameBytes)) {
+    onHighWater();
+    return false;
+  }
+
+  await new Promise<void>((resolve, reject) => {
+    let callbackUsed = false;
+    const result = socket.send(frame, (error) => {
+      callbackUsed = true;
+      if (error) reject(error);
+      else resolve();
+    });
+    if (result && typeof result.then === "function") {
+      result.then(resolve, reject);
+    } else if (socket.send.length < 2 && !callbackUsed) {
+      resolve();
+    }
+  });
+  return true;
 }
 
 export function physicalSocketHasCapacity(
@@ -73,6 +105,9 @@ export function sendBoundedPhysicalFrame(params: {
     onHighWater();
     return false;
   }
-  socket.send(frame);
+  const result = socket.send(frame);
+  if (result && typeof result.then === "function") {
+    void result.catch(() => undefined);
+  }
   return true;
 }