diff --git a/CHANGELOG.md b/CHANGELOG.md
index c91af534e..a105657ea 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 ### Pending
 - Web auto-replies now resize/recompress media and honor `inbound.reply.mediaMaxMb` in `~/.warelay/warelay.json` (default 5 MB) to avoid provider/API limits.
+- Web provider now detects media kind (image/audio/video/document), logs the source path, and enforces provider caps: images ≤6 MB, audio/video ≤16 MB, documents ≤100 MB; images still target the configurable cap above with resize + JPEG recompress.
 - Optional voice-note transcription: set `inbound.transcribeAudio.command` (e.g., OpenAI Whisper CLI) to turn inbound audio into text before templating/Claude; verbose logs surface when transcription runs. Prompts now include the original media path plus a `Transcript:` block so models see both.
 
 ## 1.0.4 — 2025-11-25
diff --git a/README.md b/README.md
index 49bbfbce0..4e143d4a4 100644
--- a/README.md
+++ b/README.md
@@ -46,10 +46,10 @@ Install from npm (global): `npm install -g warelay` (Node 22+). Then choose **on
 | `warelay webhook` | Run inbound webhook (`ingress=tailscale` updates Twilio; `none` is local-only) | `--ingress tailscale\|none` `--port <port>` `--path <path>` `--reply <text>` `--verbose` `--yes` `--dry-run` |
 | `warelay login` | Link personal WhatsApp Web via QR | `--verbose` |
 
-### Sending images
-- Twilio: `warelay send --to +1... --message "Hi" --media ./pic.jpg --serve-media` (needs `warelay webhook --ingress tailscale` or `--serve-media` to auto-host via Funnel; max 5 MB).
-- Web: `warelay send --provider web --media ./pic.jpg --message "Hi"` (local path or URL; no hosting needed).
-- Auto-replies can attach `mediaUrl` in `~/.warelay/warelay.json` (used alongside `text` when present). Web auto-replies now auto-resize/recompress images and cap size by config: set `inbound.reply.mediaMaxMb` (default 5) to control the post-compression limit; images are resized (max side 2048px) and JPEG-compressed to fit.
+### Sending media
+- Twilio: `warelay send --to +1... --message "Hi" --media ./pic.jpg --serve-media` (needs `warelay webhook --ingress tailscale` or `--serve-media` to auto-host via Funnel; max 5 MB per file because of the built-in host).
+- Web: `warelay send --provider web --media ./pic.jpg --message "Hi"` (local path or URL; no hosting needed). Web auto-detects media kind: images (≤6 MB), audio/voice or video (≤16 MB), other docs (≤100 MB). Images are resized to max 2048px and JPEG recompressed when the cap would be exceeded.
+- Auto-replies can attach `mediaUrl` in `~/.warelay/warelay.json` (used alongside `text` when present). Web auto-replies honor `inbound.reply.mediaMaxMb` (default 5 MB) as a post-compression target but will never exceed the provider hard limits above.
 
 ### Voice notes (optional transcription)
 - If you set `inbound.transcribeAudio.command`, warelay will run that CLI when inbound audio arrives (e.g., WhatsApp voice notes) and replace the Body with the transcript before templating/Claude.
diff --git a/docs/audio.md b/docs/audio.md
index c92e93cf7..1efcb5336 100644
--- a/docs/audio.md
+++ b/docs/audio.md
@@ -37,7 +37,8 @@ Requires `OPENAI_API_KEY` in env and `openai` CLI installed:
 
 ## Notes & limits
 - We don’t ship a transcriber; you opt in with any CLI that prints text to stdout (Whisper cloud, whisper.cpp, vosk, Deepgram, etc.).
-- Size guard: inbound audio must be ≤5 MB (same as other media).
+- Size guard: inbound audio must be ≤5 MB (matches the temp media store and transcript pipeline).
+- Outbound caps: Web can send audio/voice up to 16 MB (sends as a voice note with `ptt: true`); Twilio still uses the 5 MB media host guard.
 - If transcription fails, we fall back to the original body/media note; replies still go through.
 - Transcript is available to templates as `{{Transcript}}`; models get both the media path and a `Transcript:` block in the prompt when using command mode.
 
diff --git a/docs/claude-config.md b/docs/claude-config.md
index be94e1475..63e3f612e 100644
--- a/docs/claude-config.md
+++ b/docs/claude-config.md
@@ -58,7 +58,8 @@ Notes on this configuration:
 - To send an image from Claude, include a line like `MEDIA:https://example.com/pic.jpg` in the output. warelay will:
   - Host local paths for Twilio using the media server/Tailscale Funnel.
   - Send buffers directly for the Web provider.
-- Inbound media is downloaded (≤5 MB) and exposed to your templates as `{{MediaPath}}`, `{{MediaUrl}}`, and `{{MediaType}}`. You can mention this in your prompt if you want Claude to reason about the attachment. Outbound media from Claude (via `MEDIA:`) is resized/recompressed on the Web provider path; control the cap with `inbound.reply.mediaMaxMb` (default 5).
+- Inbound media is downloaded (≤5 MB) and exposed to your templates as `{{MediaPath}}`, `{{MediaUrl}}`, and `{{MediaType}}`. You can mention this in your prompt if you want Claude to reason about the attachment.
+- Outbound media from Claude (via `MEDIA:`) follows provider caps: Web resizes images to the configured target (`inbound.reply.mediaMaxMb`, default 5 MB) within hard limits of 6 MB (image), 16 MB (audio/video voice notes), and 100 MB (documents); Twilio still uses the Funnel host with a 5 MB guard.
 - Voice notes: set `inbound.transcribeAudio.command` to run a CLI that emits the transcript to stdout (e.g., OpenAI Whisper: `openai api audio.transcriptions.create -m whisper-1 -f {{MediaPath}} --response-format text`). If it succeeds, warelay replaces `Body` with the transcript and adds the original media path plus a `Transcript:` block into the prompt before invoking Claude.
 
 ## Testing the setup
diff --git a/docs/images.md b/docs/images.md
index 6a622cb30..59d982c77 100644
--- a/docs/images.md
+++ b/docs/images.md
@@ -5,6 +5,7 @@ This document defines how `warelay` should handle sending and replying with imag
 ## Goals
 - Allow sending an image with an optional caption via `warelay send` for both providers.
 - Allow auto-replies (Twilio webhook, Twilio poller, Web inbox) to return an image (optionally with text) when configured.
+- For the Web provider, also support audio/voice, video, and generic documents with sensible per-type limits.
 - Keep the “one command at a time” queue intact; media fetch/serve must not block other replies longer than necessary.
 - Avoid introducing new external services: reuse the existing Tailscale Funnel port to host media for Twilio.
 
@@ -21,10 +22,12 @@ This document defines how `warelay` should handle sending and replying with imag
 ## Provider Behavior
 ### Web (Baileys)
 - Input: local file path **or** HTTP(S) URL.
-- Flow: load into Buffer, **resize + recompress to JPEG** (max side 2048px, quality step-down) to fit under a configurable cap, then send via `sock.sendMessage(jid, { image: buffer, caption })`.
-- Size cap: default 5 MB; override with `inbound.reply.mediaMaxMb` in `~/.warelay/warelay.json`.
+- Flow: load into Buffer, detect media kind, and apply the right payload:
+  - Images: **resize + recompress to JPEG** (max side 2048px, quality step-down) to fit under `inbound.reply.mediaMaxMb` (default 5 MB) but never above the Web hard cap (6 MB).
+  - Audio/voice and video: pass through up to 16 MB; set `ptt: true` for audio to send as a voice note.
+  - Everything else becomes a document with filename, up to 100 MB.
 - Caption uses `--message` or `reply.text`; if caption is empty, send media-only.
-- Logging: non-verbose shows `↩️`/`✅` with caption; verbose includes `(media, <bytes>B, <ms>ms fetch)`.
+- Logging: non-verbose shows `↩️`/`✅` with caption; verbose includes `(media, <bytes>B, <ms>ms fetch)` and the local/remote path.
 
 ### Twilio
 - Twilio API requires a public HTTPS `MediaUrl`; it will not accept local paths.
@@ -32,7 +35,7 @@ This document defines how `warelay` should handle sending and replying with imag
 - When `--media` is a local path, copy to temp dir (`~/.warelay/media/<uuid>`), serve at `/media/<uuid>` on the existing Express app started for webhook, or spin up a short-lived server on demand for `send`.
   - `MediaUrl` = `https://<tailnet-host>.ts.net/media/<uuid>`.
   - Files auto-removed after TTL (default 2 minutes) or after first successful fetch (best-effort).
-  - Enforce size limit 5 MB; reject early with clear error.
+  - Enforce size limit 5 MB (matches the media host guard); reject early with clear error.
 - If `--media` is already an HTTPS URL, pass through unchanged.
 - Fallback: if Funnel is not enabled (or host unknown) and a local path is provided, fail with guidance to run `warelay webhook --ingress tailscale` (or pass a URL instead).
 
@@ -56,12 +59,12 @@ This document defines how `warelay` should handle sending and replying with imag
 - For completeness: when inbound Twilio/Web messages include media, download to temp file, expose templating variables:
   - `{{MediaUrl}}` original URL (Twilio) or pseudo-URL (web).
   - `{{MediaPath}}` local temp path written before running the command.
-- Size guard: only download if ≤5 MB; else skip and log.
+- Size guard: only download if ≤5 MB; else skip and log (aligns with the temp media store limit).
 - Audio/voice notes: if you set `inbound.transcribeAudio.command`, warelay will run that CLI (templated with `{{MediaPath}}`) and replace `Body` with the transcript before continuing the reply flow; verbose logs indicate when transcription runs. The command prompt includes the original media path plus a `Transcript:` section so the model sees both.
 
 ## Errors & Messaging
 - Local path with twilio + Funnel disabled → error: “Twilio media needs a public URL; start `warelay webhook --ingress tailscale` or pass an https:// URL.”
-- File too large (>5 MB) → “Media exceeds 5 MB limit; resize or host elsewhere.”
+- File too large → error mentions the applicable cap (5 MB for Twilio host, 6/16/100 MB for Web image/audio-video/doc respectively).
 - Download failure for web provider → “Failed to load media from <source>; skipping send.”
 
 ## Tests to Add
diff --git a/src/provider-web.test.ts b/src/provider-web.test.ts
index c06b309b0..4ef875524 100644
--- a/src/provider-web.test.ts
+++ b/src/provider-web.test.ts
@@ -423,7 +423,7 @@ describe("provider-web", () => {
 			sendMedia,
 		});
 
-		expect(sendMedia).toHaveBeenCalled();
+		expect(sendMedia).toHaveBeenCalledTimes(1);
 		expect(reply).toHaveBeenCalledWith("hi");
 		fetchMock.mockRestore();
 	});
@@ -501,42 +501,42 @@ describe("provider-web", () => {
 		fetchMock.mockRestore();
 	});
 
-	it(
-		"compresses common formats to jpeg under the cap",
-		{ timeout: 15_000 },
-		async () => {
-			const formats = [
-				{
-					name: "png",
-					mime: "image/png",
-					make: (buf: Buffer, opts: { width: number; height: number }) =>
-						sharp(buf, {
-							raw: { width: opts.width, height: opts.height, channels: 3 },
-						})
-							.png({ compressionLevel: 0 })
-							.toBuffer(),
-				},
-				{
-					name: "jpeg",
-					mime: "image/jpeg",
-					make: (buf: Buffer, opts: { width: number; height: number }) =>
-						sharp(buf, {
-							raw: { width: opts.width, height: opts.height, channels: 3 },
-						})
-							.jpeg({ quality: 100, chromaSubsampling: "4:4:4" })
-							.toBuffer(),
-				},
-				{
-					name: "webp",
-					mime: "image/webp",
-					make: (buf: Buffer, opts: { width: number; height: number }) =>
-						sharp(buf, {
-							raw: { width: opts.width, height: opts.height, channels: 3 },
-						})
-							.webp({ quality: 100 })
-							.toBuffer(),
-				},
-			] as const;
+		it(
+			"compresses common formats to jpeg under the cap",
+			{ timeout: 15_000 },
+			async () => {
+				const formats = [
+					{
+						name: "png",
+						mime: "image/png",
+						make: (buf: Buffer, opts: { width: number; height: number }) =>
+							sharp(buf, {
+								raw: { width: opts.width, height: opts.height, channels: 3 },
+							})
+								.png({ compressionLevel: 0 })
+								.toBuffer(),
+					},
+					{
+						name: "jpeg",
+						mime: "image/jpeg",
+						make: (buf: Buffer, opts: { width: number; height: number }) =>
+							sharp(buf, {
+								raw: { width: opts.width, height: opts.height, channels: 3 },
+							})
+								.jpeg({ quality: 100, chromaSubsampling: "4:4:4" })
+								.toBuffer(),
+					},
+					{
+						name: "webp",
+						mime: "image/webp",
+						make: (buf: Buffer, opts: { width: number; height: number }) =>
+							sharp(buf, {
+								raw: { width: opts.width, height: opts.height, channels: 3 },
+							})
+								.webp({ quality: 100 })
+								.toBuffer(),
+					},
+				] as const;
 
 			for (const fmt of formats) {
 				// Force a small cap to ensure compression is exercised for every format.