update api

Cargo.lock

@@ -139,6 +139,20 @@ dependencies = [
  "zeroize",
 ]
 
+[[package]]
+name = "aes-gcm"
+version = "0.10.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "831010a0f742e1209b3bcea8fab6a8e149051ba6099432c8cb2cc117dec3ead1"
+dependencies = [
+ "aead",
+ "aes",
+ "cipher 0.4.4",
+ "ctr",
+ "ghash",
+ "subtle",
+]
+
 [[package]]
 name = "ahash"
 version = "0.8.12"
@@ -1686,6 +1700,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "78c8292055d1c1df0cce5d180393dc8cce0abec0a7102adb6c7b1eef6016d60a"
 dependencies = [
  "generic-array",
+ "rand_core 0.6.4",
  "typenum",
 ]
 
@@ -1708,6 +1723,15 @@ dependencies = [
  "linktime-proc-macro",
 ]
 
+[[package]]
+name = "ctr"
+version = "0.9.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "0369ee1ad671834580515889b80f2ea915f23b8be8d0daa4bbaf2ac5c7590835"
+dependencies = [
+ "cipher 0.4.4",
+]
+
 [[package]]
 name = "ctutils"
 version = "0.4.2"
@@ -2542,6 +2566,16 @@ dependencies = [
  "wasm-bindgen",
 ]
 
+[[package]]
+name = "ghash"
+version = "0.5.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f0d8a4362ccb29cb0b265253fb0a2728f592895ee6854fd9bc13f2ffda266ff1"
+dependencies = [
+ "opaque-debug",
+ "polyval",
+]
+
 [[package]]
 name = "gif"
 version = "0.14.2"
@@ -5191,6 +5225,18 @@ dependencies = [
  "arrayvec",
 ]
 
+[[package]]
+name = "polyval"
+version = "0.6.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9d1fe60d06143b2430aa532c94cfe9e29783047f06c0d7fd359a9a51b729fa25"
+dependencies = [
+ "cfg-if",
+ "cpufeatures 0.2.17",
+ "opaque-debug",
+ "universal-hash",
+]
+
 [[package]]
 name = "portable-atomic"
 version = "1.15.0"
@@ -6631,7 +6677,9 @@ checksum = "6ce2be8dc25455e1f91df71bfa12ad37d7af1092ae736f3a6cd0e37bc7810596"
 name = "state"
 version = "1.0.1"
 dependencies = [
+ "aes-gcm",
  "anyhow",
+ "base64 0.22.1",
  "browser-signer-proxy",
  "common",
  "flume 0.11.1",
@@ -6650,6 +6698,7 @@ dependencies = [
  "nostr-sdk",
  "rustls",
  "serde_json",
+ "sha2 0.10.9",
  "smol",
  "webbrowser",
 ]

Cargo.toml

@@ -27,6 +27,11 @@ nostr-connect = { git = "https://github.com/rust-nostr/nostr" }
 nostr-sdk = { git = "https://github.com/rust-nostr/nostr" }
 nostr = { git = "https://github.com/rust-nostr/nostr", features = [ "nip59", "nip49", "nip44" ] }
 
+# Crypto (NIP-17 encrypted file messages)
+aes-gcm = "0.10"
+sha2 = "0.10"
+base64 = "0.22"
+
 # Others
 anyhow = "1.0.44"
 chrono = { version = "0.4.38", features = ["wasmbind"] }

PLAN.md

@@ -0,0 +1,452 @@
+# NIP-17 Encrypted File Messages (kind 15) — Backend Plan
+
+Implementation plan for sending and receiving NIP-17 **file messages** in coop.
+
+**Scope: backend only.** This document covers crypto, blob upload/download, rumor
+construction, rumor parsing and local caching. No UI work (composer button, file
+rendering, image cache, decryption-on-render state) — that is a separate follow-up
+once these APIs exist.
+
+---
+
+## 1. What the protocol requires
+
+NIP-17 file messages are **not** a new transport. They reuse everything coop already
+has (NIP-44, NIP-59 seal + gift wrap, kind 10050 inbox relays) and only add:
+
+1. A new inner **rumor kind: `15`** (`Kind::Custom(15)`), whose `.content` is the URL
+   of an **encrypted** blob and whose tags carry the MIME type and the decryption
+   material.
+2. **AES-256-GCM** encryption of the file bytes before upload.
+
+Kind 15 tags (per NIP-17):
+
+| Tag | Required | Meaning |
+|---|---|---|
+| `p` | yes | receivers (as for kind 14) |
+| `e` | if reply | parent message id |
+| `subject` | optional | conversation title |
+| `file-type` | yes | MIME type of the **plaintext** file |
+| `encryption-algorithm` | yes | `aes-gcm` (only supported value) |
+| `decryption-key` | yes | key for the recipient |
+| `decryption-nonce` | yes | nonce for the recipient |
+| `x` | yes | SHA-256 hex of the **encrypted** file |
+| `ox` | expected | SHA-256 hex of the file **before** encryption |
+| `size` | optional | size of the **encrypted** file in bytes |
+| `dim` | optional | `<width>x<height>` in pixels |
+| `thumbhash` / `blurhash` | optional | placeholder previews |
+| `thumb` | optional | thumbnail URL (same key/nonce) |
+| `fallback` | optional | extra file sources (same key/nonce) |
+
+Key material travels **inside** the gift wrap, so the public blob URL is useless
+without it. That property falls out of the existing seal/gift-wrap code for free.
+
+`thumbhash`, `blurhash`, `thumb`, `fallback` are out of scope for v1 (all optional).
+
+---
+
+## 2. What already exists in coop (verified against the pinned deps)
+
+| Requirement | Location | Status |
+|---|---|---|
+| NIP-59 seal + gift wrap | `crates/chat/src/room.rs::send_gift_wrap` (`nip59::GiftWrapBuilder`) | exists |
+| Per-recipient publish + self backup | `crates/chat/src/room.rs::send` | exists |
+| Inbox relays (kind 10050) | `crates/chat/src/lib.rs::handle_notifications` | exists |
+| Rumor unwrap + local cache | `crates/chat/src/lib.rs::{extract_rumor,try_unwrap_with,set_rumor,get_rumor}` | exists |
+| Kind 14 rumor construction | `crates/chat/src/room.rs::rumor` | exists |
+| Blossom upload | `crates/state/src/blossom.rs::upload` (plaintext, random signing key) | partial |
+| **Kind 15 rumor + parse** | — | **to add** |
+| **AES-256-GCM encrypt/decrypt** | — | **to add** |
+| **Encrypted blob upload/download** | — | **to add** |
+
+Verified facts about the pinned SDK (`rust-nostr@b230cec`, `nostr 0.45.4`) and
+`gpui@69af529`:
+
+- rust-nostr has **no** kind-15 helper and **no** AES-GCM/AES-GCM-tag support anywhere
+  (`FileMetadata` in NIP-94 is kind 1063, unrelated). `nip17.rs` only covers kind 14
+  and 10050.
+- `nip59::GiftWrapBuilder::new(receiver, rumor: UnsignedEvent)` accepts **any**
+  `UnsignedEvent`, so kind 15 flows through the existing wrap/send path unchanged.
+- `Kind` has no named variant for 15; `Kind::Custom(15)` is required, and
+  `Kind: Display` prints `as_u16()`, so `rumor.kind.to_string()` yields `"15"`.
+- `nostr::nips::nip94::Sha256Hash` is public (`from_byte_array`, `to_hex`, `Display`,
+  `from_hex`) even though it lives in the nip94 module — usable for `x`/`ox` hex
+  formatting without a new hashing crate.
+- `gpui::App::http_client()` returns `Arc<dyn HttpClient>` and
+  `gpui_web/src/http_client.rs` implements it, so HTTP download is cross-platform.
+  `AsyncApp` exposes `update(|app| ...)`, which is how backend async code reaches it.
+- `nostr-blossom` exposes `upload_blob`, `get_blob`, `has_blob`, `list_blobs`,
+  `delete_blob`.
+- The `k` tag is currently hardcoded to `"14"` in two places
+  (`room.rs::send_gift_wrap`, `lib.rs::set_rumor`) and used as a room-list filter
+  (`lib.rs::get_rooms_task`, `custom_tag(LOWERCASE_K, "14")`).
+
+---
+
+## 3. Dependencies
+
+Add to `[workspace.dependencies]` in `Cargo.toml`, then reference from the crates below.
+
+```toml
+aes-gcm = "0.10"   # NEW - RustCrypto: Aes256Gcm, aead::{Aead, KeyInit, OsRng}
+sha2    = "0.10"   # NEW (already in Cargo.lock, cached) - SHA-256 for x / ox
+base64  = "0.22"   # NEW as a direct dep (already in the tree transitively)
+```
+
+- No new RNG dependency: `aes_gcm::aead::OsRng` (the wasm getrandom backends are
+  already configured in `web/Cargo.toml`).
+- No new hashing/hex dependency: `sha2` output → `nostr::nips::nip94::Sha256Hash::from_byte_array(...).to_hex()`.
+- `aes-gcm` is the only crate that needs a crates.io fetch (`aes 0.8` / `aead 0.5` are
+  already in the lock file), so it is a small addition to the build graph.
+- Hand-rolling AES-GCM is explicitly **not** an option.
+
+---
+
+## 4. Layering and type ownership
+
+`chat` depends on `state` (see `crates/chat/Cargo.toml`), never the reverse, so the
+shared types and tag names must live in `state`.
+
+- `crates/state/src/file.rs` (new) owns:
+  - `EncryptedFile`, `FileAttachment`, the tag-name constants, `ALGORITHM = "aes-gcm"`
+  - `encrypt` / `decrypt` / `sha256_hex`
+  - `FileAttachment::from_tags` / `FileAttachment::tags` (single source of truth for
+    tag names, so build and parse can't drift)
+  - `upload_encrypted`, `download_and_decrypt`
+  - re-exported from `crates/state/src/lib.rs`: `mod file; pub use file::*;`
+- `crates/chat` consumes it: `message.rs` (parse into `Message`), `room.rs`
+  (build kind-15 rumor), `lib.rs` (cache tag + room list query).
+- `crates/chat` should re-export the type for the future UI layer:
+  `pub use state::FileAttachment;` in `crates/chat/src/lib.rs`.
+
+---
+
+## 5. Data flow (backend)
+
+```mermaid
+flowchart TD
+    A[caller: path + blossom server] --> B[read bytes + guess mime]
+    B --> C[encrypt: random 32B key, 12B nonce, AES-256-GCM]
+    C --> D[sha256 ciphertext = x, sha256 plaintext = ox]
+    D --> E[Blossom upload ciphertext]
+    E --> F[FileAttachment]
+    F --> G[Room::file_rumor -> kind 15 rumor]
+    G --> H[Room::send -> existing NIP-59 wrap per member + self backup]
+    H --> I[existing extract_rumor on receiver]
+    I --> J[Message.file]
+    J --> K[download_and_decrypt: GET url, verify x, decrypt]
+```
+
+---
+
+## 6. Implementation steps
+
+### Step 1 — Dependencies
+
+Add the three lines from section 3 and wire them into `crates/state/Cargo.toml`
+(`aes-gcm`, `sha2`, `base64`). Run `cargo check -p state` to confirm the fetch works.
+
+### Step 2 — `crates/state/src/file.rs` (new, ~180 LOC)
+
+```rust
+use aes_gcm::aead::{Aead, KeyInit, OsRng};
+use aes_gcm::{AeadCore, Aes256Gcm, Key, Nonce};
+use nostr::nips::nip94::Sha256Hash;
+use sha2::{Digest, Sha256};
+
+pub const ALGORITHM: &str = "aes-gcm";
+/// Ciphertext hash tag (NIP-17).
+const TAG_SHA256: &str = "x";
+const TAG_ORIGINAL_SHA256: &str = "ox";
+const TAG_FILE_TYPE: &str = "file-type";
+const TAG_ALGORITHM: &str = "encryption-algorithm";
+const TAG_KEY: &str = "decryption-key";
+const TAG_NONCE: &str = "decryption-nonce";
+const TAG_SIZE: &str = "size";
+const TAG_DIM: &str = "dim";
+const TAG_ALT: &str = "alt";
+
+/// Maximum blob size accepted when downloading (bytes). See edge cases.
+pub const MAX_FILE_SIZE: usize = 25 * 1024 * 1024;
+
+/// Result of encrypting a file: ciphertext to upload plus NIP-17 key material.
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub struct EncryptedFile {
+    pub data: Vec<u8>,
+    /// base64-encoded 32-byte key
+    pub key: String,
+    /// base64-encoded 12-byte nonce
+    pub nonce: String,
+}
+
+/// NIP-17 kind 15 attachment metadata (tags + `.content` URL).
+#[derive(Debug, Clone, PartialEq, Eq, PartialOrd, Ord)]
+pub struct FileAttachment {
+    pub url: Url,
+    pub mime: String,
+    pub key: String,
+    pub nonce: String,
+    pub sha256: Option<String>,
+    pub original_sha256: Option<String>,
+    pub size: Option<u64>,
+    pub dim: Option<(u32, u32)>,
+    /// Non-standard display name (see "Open decisions" #2).
+    pub name: Option<String>,
+}
+
+impl FileAttachment {
+    /// Build the NIP-17 tags for a kind 15 rumor.
+    pub fn tags(&self) -> Vec<Tag>;
+    /// Parse a kind 15 rumor's tags. Returns `None` if key material is missing
+    /// or `encryption-algorithm` is not `aes-gcm`.
+    pub fn from_tags(tags: &Tags) -> Option<Self>;
+    pub fn is_image(&self) -> bool;
+    pub fn display_name(&self) -> SharedString; // falls back to mime/size
+}
+
+/// AES-256-GCM encrypt with a fresh random key and nonce.
+pub fn encrypt(data: &[u8]) -> Result<EncryptedFile>;
+/// AES-256-GCM decrypt using the values from a kind 15 rumor.
+pub fn decrypt(data: &[u8], key: &str, nonce: &str) -> Result<Vec<u8>>;
+
+/// Lowercase hex SHA-256, matching the NIP-94 `x`/`ox` convention.
+pub fn sha256_hex(data: &[u8]) -> String;
+
+/// Read a file, encrypt it, upload the ciphertext to Blossom, return the attachment.
+#[cfg(not(target_arch = "wasm32"))]
+pub async fn upload_encrypted(server: Url, path: PathBuf, cx: &AsyncApp) -> Result<FileAttachment>;
+
+/// Fetch the blob, verify its SHA-256 against `expected_sha256`, then decrypt.
+pub async fn download_and_decrypt(
+    url: &Url,
+    key: &str,
+    nonce: &str,
+    expected_sha256: Option<&str>,
+    cx: &AsyncApp,
+) -> Result<Vec<u8>>;
+```
+
+Implementation notes, in priority order:
+
+1. **Compute `x` and `ox` locally with `sha256_hex`.** Do **not** derive `x` from
+   `BlobDescriptor::sha256` — that field is a `bitcoin_hashes::sha256::Hash` whose
+   `Display` byte order could not be confirmed from the vendored sources, and a
+   reversed digest would silently break integrity checks in other clients. Use the
+   Blossom response only for `blob.url`. (`sha2` → `Sha256Hash::from_byte_array(...).to_hex()`
+   gives the conventional digest order and is unambiguous.)
+2. **Key/nonce decoding must be tolerant.** NIP-17 does not specify an encoding:
+   accept base64 standard (padded and unpadded), base64url, and hex on read; emit
+   base64 standard on write. See "Open decisions" #1.
+3. Validate sizes after decoding: key must be exactly 32 bytes, nonce exactly 12.
+   Return a descriptive error otherwise.
+4. `decrypt` must fail closed on a bad tag (GCM authentication failure) — never
+   return partial plaintext.
+5. `upload_encrypted` mirrors the existing `state::blossom::upload` shape:
+   `smol::fs::read` + `mime_guess::from_path`, `BlossomClient::new(server)`,
+   `upload_blob(ciphertext, Some("application/octet-stream"), None, Some(&keys))`
+   wrapped in `Tokio::spawn(cx, ...)`. Note the content type describes the
+   **ciphertext**; the plaintext MIME goes in the `file-type` tag.
+   On `wasm32` return `Err(anyhow!("File upload not supported on web"))`, matching
+   the existing stub in `blossom.rs`.
+6. `download_and_decrypt` uses gpui's HTTP client
+   (`cx.update(|app| app.http_client())`, then
+   `client.get(url.as_str(), AsyncBody::default(), true)`), reads the body with
+   `futures::AsyncReadExt`, caps the read at `MAX_FILE_SIZE + 1` and rejects anything
+   larger, verifies `sha256_hex(&ciphertext)` against `expected_sha256`
+   (case-insensitive) when present, then decrypts. This path works on desktop and web.
+7. `size` in `FileAttachment` is the **ciphertext** size (per the NIP wording), i.e.
+   `encrypted.data.len()`. `dim` is optional; if wanted, decode dimensions with the
+   `image` crate (`image::ImageReader`) — mark as a nice-to-have, not a blocker.
+8. `encrypt` should take `&[u8]` (not a path) so it stays pure and testable without I/O.
+
+### Step 3 — `crates/chat/src/message.rs` (~80 LOC)
+
+- Add the kind constant next to `Message`:
+
+  ```rust
+  /// NIP-17 file message (rust-nostr has no named `Kind` variant for 15).
+  pub const KIND_FILE_MESSAGE: Kind = Kind::Custom(15);
+  ```
+
+- Add the field:
+
+  ```rust
+  pub struct Message {
+      // ... existing fields ...
+      /// Encrypted file attachment (NIP-17 kind 15)
+      pub file: Option<FileAttachment>,
+  }
+  ```
+
+- In all three `From` impls (`&Event`, `&UnsignedEvent`, `&NewMessage`), parse from
+  tags when `kind == KIND_FILE_MESSAGE`, and when a file is present **do not** run
+  `extract_and_remove_media_urls` or `extract_mentions` on `.content` — for kind 15
+  `.content` is a ciphertext URL that must never be rendered as text or as media:
+
+  ```rust
+  let file = (val.kind == KIND_FILE_MESSAGE)
+      .then(|| FileAttachment::from_tags(&val.tags))
+      .flatten();
+
+  let (media, content) = if file.is_some() {
+      (vec![], String::new())
+  } else {
+      extract_and_remove_media_urls(&val.content)
+  };
+  ```
+
+- Add a helper for non-UI consumers that display a message one-line
+  (reply previews, notifications, copy):
+
+  ```rust
+  /// Single-line representation: text for kind 14, `[File] <name>` for kind 15.
+  pub fn preview(&self) -> SharedString;
+  ```
+
+- `Ord`/`Eq`/`Hash` are keyed on `id`/`created_at`, so adding the field does not
+  change `Message` ordering semantics.
+
+### Step 4 — `crates/chat/src/room.rs` (~70 LOC)
+
+- Extract the shared tag logic from `rumor()` into a private helper so kind 14 and
+  kind 15 cannot drift:
+
+  ```rust
+  /// `subject` + reply `e` tags + receiver `p` tags (excluding `sender`).
+  fn conversation_tags(&self, replies: &[EventId], sender: PublicKey, cx: &App) -> Vec<Tag>;
+  ```
+
+  `rumor()` then becomes `EventBuilder::new(kind, content).tags(self.conversation_tags(...))`,
+  and gains no behavior change.
+
+- Add:
+
+  ```rust
+  /// Build a NIP-17 kind 15 (file message) rumor.
+  ///
+  /// WARNING: never sign and send this event to relays; it is only ever wrapped.
+  pub fn file_rumor<I>(&self, file: FileAttachment, replies: I, cx: &App) -> Option<UnsignedEvent>
+  where
+      I: IntoIterator<Item = EventId>,
+  {
+      // tags = conversation_tags(...) ++ file.tags()
+      // content = file.url.to_string()
+      // EventBuilder::new(KIND_FILE_MESSAGE, content).tags(tags).finalize_unsigned(sender)
+      // then event.ensure_id()
+  }
+  ```
+
+- Fix the gift wrap's `k` tag so relays see the real inner kind
+  (`send_gift_wrap`, currently hardcoded):
+
+  ```rust
+  let k_tag = Tag::custom("k", [rumor.kind.to_string()]);
+  ```
+
+- `Room::send` needs **no change**: it already accepts any `UnsignedEvent`, and the
+  self-backup branch publishes the same rumor wrapped for the sender, so the sender's
+  other devices receive the file message with the same key material.
+
+### Step 5 — `crates/chat/src/lib.rs` (~5 LOC)
+
+- `set_rumor`: store the real kind in the local cache tag:
+
+  ```rust
+  Tag::custom("k", [rumor.kind.to_string()]),
+  ```
+
+- `get_rooms_task` currently filters `custom_tag(SingleLetterTag::LOWERCASE_K, "14")`,
+  which would hide rooms whose only messages are file messages. Simplest fix: drop
+  the `k` filter and keep `.kind(Kind::ApplicationSpecificData)`; the existing
+  in-loop JSON parse plus `tags.public_keys().next().is_some()` check already
+  discards junk, and kind 30078 rows in the local DB exist only for this rumor cache.
+  Fallback if the extra rows are a concern: run two queries (`k = "14"` and
+  `k = "15"`) and merge the results.
+
+- No changes to `handle_notifications`, `extract_rumor`, `try_unwrap_with`, `new_message`,
+  `Room::get_messages` — all are already kind-agnostic. (`Room::get_messages` filters
+  only on the `r` room tag, so file messages load with the rest of the history.)
+
+### Step 6 — (out of scope) UI wiring
+
+Composer entry point, decryption cache, image/file rendering live in
+`crates/chat_ui`. Not part of this plan; the APIs above are what that layer needs:
+`state::upload_encrypted`, `FileAttachment::tags/from_tags`, `Room::file_rumor`,
+`Room::send`, `state::download_and_decrypt`.
+
+---
+
+## 7. Open decisions
+
+1. **Key/nonce encoding (interop risk — decide/verify first).** NIP-17 does not specify
+   how `decryption-key` / `decryption-nonce` are encoded, and no reference
+   implementation could be reached from this environment to confirm. Plan: emit
+   **base64 standard**, accept base64 std/unpadded/url-safe/hex on read. Before
+   release, verify against another NIP-17 client (0xchat, Amethyst) and tighten if
+   needed. Everything else in the plan is encoding-agnostic.
+2. **Display name.** The NIP defines no filename tag and Blossom URLs end in a content
+   hash, so a name has to come from a non-standard tag. Proposal: emit
+   `["alt", <file name>]` (NIP-94 tag; NIP-17 allows "rest of tags", and `alt` is a
+   benign a11y field), tolerate its absence, fall back to mime + size. Alternative:
+   ship strictly spec-shaped and show mime + size only.
+3. **`thumbhash`/`blurhash`/`thumb`/`fallback`/`dim`**: all optional; recommend skipping
+   in v1 (and letting the UI show a placeholder until the blob is decrypted).
+4. **Web (wasm)**: encrypted upload stays unsupported on web, matching today's
+   `state::blossom::upload` stub. Download/decrypt is cross-platform via gpui's client.
+5. **Ciphertext caching**: recommend *not* persisting decrypted plaintext in the local
+   database in v1; decryption happens on demand from the blob URL.
+
+---
+
+## 8. Edge cases and failure handling
+
+| Case | Behavior |
+|---|---|
+| `encryption-algorithm` != `aes-gcm` | do not decrypt; report "unsupported encryption" (forward compatibility) |
+| missing `decryption-key` / `decryption-nonce` | `FileAttachment::from_tags` returns `None` → surfaced as a failed message, not a panic |
+| key != 32 bytes or nonce != 12 bytes | descriptive error |
+| GCM authentication failure | error; never emit partial plaintext |
+| `sha256_hex(ciphertext) != x` | error (tampered or corrupted blob), checked **before** decrypting |
+| blob larger than `MAX_FILE_SIZE` | rejected while reading the body |
+| HTTP error / non-200 | error message including status |
+| `content` not a valid URL | error; message still cached so it renders as a failed attachment |
+| sender's own copy | works automatically via the existing self-backup gift wrap |
+| multiple receivers | one blob, one key, key re-sent inside each recipient's gift wrap |
+
+---
+
+## 9. Verification
+
+The feature cannot be exercised end-to-end without the UI step (out of scope), so
+backend verification is:
+
+1. `cargo check -p state -p chat` after each step.
+2. `cargo check -p coop_web --target wasm32-unknown-unknown` to confirm the
+   `cfg(target_arch = "wasm32")` stubs and the new module compile for web.
+3. Cheap unit checks (no network, ~15 LOC in `state/src/file.rs`), despite "no tests
+   required" for the feature, because these are pure functions and catch the two
+   riskiest bugs — encoding and tag ordering:
+   - `encrypt` → `decrypt` round trip returns the original bytes.
+   - flipping one ciphertext bit makes `decrypt` fail.
+   - `sha256_hex(b"abc") == "ba7816bf8f01cfea414140de5dae2223b00361a396177a9cb410ff61f20015ad"`
+     (confirms the digest order used for `x`/`ox`).
+   - `FileAttachment` tags → `from_tags` round trip preserves key/nonce/mime/url.
+4. End-to-end (requires the UI step or a temporary call site): send to self with
+   `RoomConfig::backup` enabled and confirm the rumor unwraps, downloads, verifies and
+   decrypts; then a second account; then a cross-client check for decision #1.
+
+---
+
+## 10. Estimated size
+
+| File | Change | ~LOC |
+|---|---|---|
+| `Cargo.toml`, `crates/state/Cargo.toml` | deps | 6 |
+| `crates/state/src/file.rs` | new | 180 |
+| `crates/state/src/lib.rs` | module + re-export | 2 |
+| `crates/chat/src/message.rs` | parse + preview | 80 |
+| `crates/chat/src/room.rs` | `file_rumor` + tag refactor + `k` tag | 70 |
+| `crates/chat/src/lib.rs` | cache tag + room list query | 5 |
+
+Order of work: 1 → 2 → 3 → 4 → 5, each step compiling on its own. Steps 2–4 are
+independent of any UI change, so the branch stays green without touching `chat_ui`.

crates/chat/src/lib.rs

@@ -21,6 +21,7 @@ mod room;
 
 pub use message::*;
 pub use room::*;
+pub use state::FileAttachment;
 
 /// A static keypair used only for signing locally-cached rumor events.
 static LOCAL_KEYS: LazyLock<Keys> = LazyLock::new(Keys::generate);
@@ -629,7 +630,7 @@ impl ChatRegistry {
 
     /// Load all rooms from the database.
     pub fn get_rooms(&mut self, cx: &mut Context<Self>) {
-        let task = self.get_rooms_task(cx);
+        let task = self.query_chat_rooms(cx);
 
         self.tasks.push(cx.spawn(async move |this, cx| {
             match task.await {
@@ -650,8 +651,8 @@ impl ChatRegistry {
         }));
     }
 
-    /// Create a task to load rooms from the database
-    fn get_rooms_task(&self, cx: &App) -> Task<Result<HashSet<Room>, Error>> {
+    /// Query the chat rooms from the database
+    fn query_chat_rooms(&self, cx: &App) -> Task<Result<HashSet<Room>, Error>> {
         let nostr = NostrRegistry::global(cx);
         let client = nostr.read(cx).client();
         let signer = nostr.read(cx).signer();
@@ -677,7 +678,7 @@ impl ChatRegistry {
 
             let filter = Filter::new()
                 .kind(Kind::ApplicationSpecificData)
-                .custom_tag(SingleLetterTag::LOWERCASE_K, "14");
+                .custom_tags(SingleLetterTag::LOWERCASE_K, ["7", "14", "15"]);
 
             let events = client.database().query(filter).await?;
             let mut grouped: HashMap<u64, Vec<UnsignedEvent>> = HashMap::new();
@@ -719,8 +720,8 @@ impl ChatRegistry {
 
     /// Parse a nostr event into a message and push it to the belonging room
     ///
-    /// If the room doesn't exist, it will be created.
-    /// Updates room ordering based on the most recent messages.
+    /// - If the room doesn't exist, it will be created.
+    /// - Updates room ordering based on the most recent messages.
     pub fn new_message(&mut self, message: NewMessage, cx: &mut Context<Self>) {
         let nostr = NostrRegistry::global(cx);
 
@@ -823,7 +824,7 @@ async fn set_rumor(client: &Client, id: EventId, rumor: &UnsignedEvent) -> Resul
         Tag::identifier(id),
         Tag::public_key(rumor.pubkey),
         Tag::custom("r", [room_id]),
-        Tag::custom("k", ["14"]),
+        Tag::custom("k", [rumor.kind.to_string()]),
     ];
 
     let event = EventBuilder::new(Kind::ApplicationSpecificData, rumor.as_json())

crates/chat/src/message.rs

@@ -4,6 +4,9 @@ use std::ops::Range;
 use common::{EventExt, NostrParser, extract_and_remove_media_urls};
 use gpui::{SharedString, SharedUri};
 use nostr_sdk::prelude::*;
+use state::FileAttachment;
+
+pub const KIND_FILE_MESSAGE: Kind = Kind::Custom(15);
 
 /// Rendered message.
 #[derive(Debug, Clone)]
@@ -21,61 +24,90 @@ pub struct Message {
     pub mentions: Vec<Mention>,
     /// List of event of the message this message is a reply to
     pub replies_to: Vec<EventId>,
+    /// Encrypted file attachment
+    pub file: Option<FileAttachment>,
 }
 
 impl From<&Event> for Message {
     fn from(val: &Event) -> Self {
-        let mentions = extract_mentions(&val.content);
-        let replies_to = extract_reply_ids(&val.tags);
-        let (media, string) = extract_and_remove_media_urls(&val.content);
-
-        Self {
-            id: val.id,
-            author: val.pubkey,
-            content: string,
-            media,
-            created_at: val.created_at,
-            mentions,
-            replies_to,
-        }
+        from_parts(
+            val.id,
+            val.pubkey,
+            val.created_at,
+            val.kind,
+            &val.content,
+            &val.tags,
+        )
     }
 }
 
 impl From<&UnsignedEvent> for Message {
     fn from(val: &UnsignedEvent) -> Self {
-        let mentions = extract_mentions(&val.content);
-        let replies_to = extract_reply_ids(&val.tags);
-        let (media, string) = extract_and_remove_media_urls(&val.content);
-
-        Self {
+        from_parts(
             // Event ID must be known
-            id: val.id.unwrap(),
-            author: val.pubkey,
-            content: string,
-            media,
-            created_at: val.created_at,
-            mentions,
-            replies_to,
-        }
+            val.id.unwrap(),
+            val.pubkey,
+            val.created_at,
+            val.kind,
+            &val.content,
+            &val.tags,
+        )
     }
 }
 
 impl From<&NewMessage> for Message {
     fn from(val: &NewMessage) -> Self {
-        let mentions = extract_mentions(&val.rumor.content);
-        let replies_to = extract_reply_ids(&val.rumor.tags);
-        let (media, string) = extract_and_remove_media_urls(&val.rumor.content);
-
-        Self {
+        from_parts(
             // Event ID must be known
-            id: val.rumor.id.unwrap(),
-            author: val.rumor.pubkey,
-            content: string,
-            media,
-            created_at: val.rumor.created_at,
-            mentions,
-            replies_to,
-        }
+            val.rumor.id.unwrap(),
+            val.rumor.pubkey,
+            val.rumor.created_at,
+            val.rumor.kind,
+            &val.rumor.content,
+            &val.rumor.tags,
+        )
+    }
+}
+
+fn from_parts(
+    id: EventId,
+    author: PublicKey,
+    created_at: Timestamp,
+    kind: Kind,
+    content: &str,
+    tags: &Tags,
+) -> Message {
+    let file = if kind == KIND_FILE_MESSAGE {
+        FileAttachment::from_tags(content, tags)
+    } else {
+        None
+    };
+    let has_file = file.is_some();
+
+    let replies_to = extract_reply_ids(tags);
+
+    // For file messages `.content` is the encrypted blob URL, not text or media
+    let mentions = if has_file {
+        Vec::new()
+    } else {
+        extract_mentions(content)
+    };
+
+    let (media, content) = if has_file {
+        (Vec::new(), String::new())
+    } else {
+        extract_and_remove_media_urls(content)
+    };
+
+    Message {
+        id,
+        author,
+        content,
+        media,
+        created_at,
+        mentions,
+        replies_to,
+        file,
     }
 }
 
@@ -105,6 +137,17 @@ impl Hash for Message {
     }
 }
 
+impl Message {
+    /// Single-line representation for reply previews, notifications and copy.
+    pub fn preview(&self) -> SharedString {
+        if let Some(file) = &self.file {
+            return format!("[File] {}", file.display_name()).into();
+        }
+
+        self.content.clone().into()
+    }
+}
+
 /// New message.
 #[derive(Debug, Clone, PartialEq, Eq, PartialOrd, Ord)]
 pub struct NewMessage {

crates/chat/src/room.rs

@@ -12,7 +12,7 @@ use person::{Person, PersonRegistry};
 use settings::{RoomConfig, SignerKind};
 use state::{NostrRegistry, TIMEOUT, UniversalSigner};
 
-use crate::NewMessage;
+use crate::{FileAttachment, KIND_FILE_MESSAGE, NewMessage};
 
 const NO_DEKEY: &str = "User hasn't set up a decoupled encryption key yet.";
 const USER_NO_DEKEY: &str = "You haven't set up a decoupled encryption key or it's not available.";
@@ -439,12 +439,52 @@ impl Room {
         let content: String = content.into();
         let replies: Vec<EventId> = replies.into_iter().collect();
 
-        let persons = PersonRegistry::global(cx);
+        // Get current user's public key
         let nostr = NostrRegistry::global(cx);
+        let sender = nostr.read(cx).current_user()?;
+
+        // Construct a direct message rumor event
+        // WARNING: never sign and send this event to relays
+        let mut event = EventBuilder::new(kind, content)
+            .tags(self.conversation_tags(&replies, sender, cx))
+            .finalize_unsigned(sender);
+
+        // Ensure that the ID is set
+        event.ensure_id();
+
+        Some(event)
+    }
+
+    // Construct a rumor event for an encrypted file message (NIP-17 kind 15)
+    pub fn file_rumor<I>(&self, file: FileAttachment, replies: I, cx: &App) -> Option<UnsignedEvent>
+    where
+        I: IntoIterator<Item = EventId>,
+    {
+        let replies: Vec<EventId> = replies.into_iter().collect();
 
         // Get current user's public key
+        let nostr = NostrRegistry::global(cx);
         let sender = nostr.read(cx).current_user()?;
 
+        let mut tags = self.conversation_tags(&replies, sender, cx);
+        tags.extend(file.tags());
+
+        // Construct a file message rumor event
+        // WARNING: never sign and send this event to relays
+        let mut event = EventBuilder::new(KIND_FILE_MESSAGE, file.url.to_string())
+            .tags(tags)
+            .finalize_unsigned(sender);
+
+        // Ensure that the ID is set
+        event.ensure_id();
+
+        Some(event)
+    }
+
+    // Build the `subject` + reply `e` tags + receiver `p` tags (excluding `sender`)
+    fn conversation_tags(&self, replies: &[EventId], sender: PublicKey, cx: &App) -> Vec<Tag> {
+        let persons = PersonRegistry::global(cx);
+
         // Construct event's tags
         let mut tags = vec![];
 
@@ -454,8 +494,8 @@ impl Room {
         }
 
         // Add all reply tags
-        for id in replies.into_iter() {
-            tags.push(Tag::event(id))
+        for id in replies {
+            tags.push(Tag::event(*id))
         }
 
         // Add all receiver tags (no intermediate allocation)
@@ -467,16 +507,7 @@ impl Room {
             }));
         }
 
-        // Construct a direct message rumor event
-        // WARNING: never sign and send this event to relays
-        let mut event = EventBuilder::new(kind, content)
-            .tags(tags)
-            .finalize_unsigned(sender);
-
-        // Ensure that the ID is set
-        event.ensure_id();
-
-        Some(event)
+        tags
     }
 
     /// Select the appropriate signer based on signer kind and available keys.
@@ -609,7 +640,7 @@ async fn send_gift_wrap(
     rumor: &UnsignedEvent,
     config: &SignerKind,
 ) -> Result<SendReport, Error> {
-    let k_tag = Tag::custom("k", vec!["14"]);
+    let k_tag = Tag::custom("k", [rumor.kind.to_string()]);
     let mut extra_tags = vec![k_tag];
 
     // Determine the receiver public key based on the config

crates/state/Cargo.toml

@@ -24,6 +24,10 @@ serde_json.workspace = true
 
 mime_guess = "2.0.4"
 
+aes-gcm.workspace = true
+sha2.workspace = true
+base64.workspace = true
+
 [target.'cfg(target_arch = "wasm32")'.dependencies]
 nostr-memory.workspace = true
 

crates/state/src/file.rs

@@ -0,0 +1,274 @@
+use std::path::PathBuf;
+
+use aes_gcm::aead::consts::U12;
+use aes_gcm::aead::{Aead, AeadCore, KeyInit, OsRng};
+use aes_gcm::{Aes256Gcm, Nonce};
+use anyhow::{Error, anyhow, bail};
+use base64::Engine as _;
+use base64::engine::general_purpose::{STANDARD, STANDARD_NO_PAD, URL_SAFE, URL_SAFE_NO_PAD};
+use futures::AsyncReadExt;
+use gpui::http_client::AsyncBody;
+use gpui::{AsyncApp, SharedString};
+use nostr::nips::nip94::Sha256Hash;
+use nostr_sdk::prelude::*;
+use sha2::{Digest, Sha256};
+
+#[cfg(not(target_arch = "wasm32"))]
+use gpui_tokio::Tokio;
+#[cfg(not(target_arch = "wasm32"))]
+use mime_guess::from_path;
+#[cfg(not(target_arch = "wasm32"))]
+use nostr_blossom::prelude::*;
+
+pub const ALGORITHM: &str = "aes-gcm";
+
+pub const MAX_FILE_SIZE: usize = 25 * 1024 * 1024;
+
+const TAG_SHA256: &str = "x";
+const TAG_ORIGINAL_SHA256: &str = "ox";
+const TAG_FILE_TYPE: &str = "file-type";
+const TAG_ALGORITHM: &str = "encryption-algorithm";
+const TAG_KEY: &str = "decryption-key";
+const TAG_NONCE: &str = "decryption-nonce";
+const TAG_SIZE: &str = "size";
+const TAG_DIM: &str = "dim";
+const TAG_ALT: &str = "alt";
+
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub struct EncryptedFile {
+    pub data: Vec<u8>,
+    pub key: String,
+    pub nonce: String,
+}
+
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub struct FileAttachment {
+    pub url: Url,
+    pub mime: String,
+    pub key: String,
+    pub nonce: String,
+    pub sha256: Option<String>,
+    pub original_sha256: Option<String>,
+    pub size: Option<u64>,
+    pub dim: Option<(u32, u32)>,
+    pub name: Option<String>,
+}
+
+impl FileAttachment {
+    pub fn tags(&self) -> Vec<Tag> {
+        let mut tags = vec![
+            Tag::custom(TAG_FILE_TYPE, [self.mime.clone()]),
+            Tag::custom(TAG_ALGORITHM, [ALGORITHM]),
+            Tag::custom(TAG_KEY, [self.key.clone()]),
+            Tag::custom(TAG_NONCE, [self.nonce.clone()]),
+        ];
+
+        if let Some(sha256) = &self.sha256 {
+            tags.push(Tag::custom(TAG_SHA256, [sha256.clone()]));
+        }
+
+        if let Some(original_sha256) = &self.original_sha256 {
+            tags.push(Tag::custom(TAG_ORIGINAL_SHA256, [original_sha256.clone()]));
+        }
+
+        if let Some(size) = self.size {
+            tags.push(Tag::custom(TAG_SIZE, [size.to_string()]));
+        }
+
+        if let Some((width, height)) = self.dim {
+            tags.push(Tag::custom(TAG_DIM, [format!("{width}x{height}")]));
+        }
+
+        if let Some(name) = &self.name {
+            tags.push(Tag::custom(TAG_ALT, [name.clone()]));
+        }
+
+        tags
+    }
+
+    pub fn from_tags(content: &str, tags: &Tags) -> Option<Self> {
+        if tag_value(tags, TAG_ALGORITHM)? != ALGORITHM {
+            return None;
+        }
+
+        Some(Self {
+            url: Url::parse(content).ok()?,
+            mime: tag_value(tags, TAG_FILE_TYPE)?.to_string(),
+            key: tag_value(tags, TAG_KEY)?.to_string(),
+            nonce: tag_value(tags, TAG_NONCE)?.to_string(),
+            sha256: tag_value(tags, TAG_SHA256).map(str::to_string),
+            original_sha256: tag_value(tags, TAG_ORIGINAL_SHA256).map(str::to_string),
+            size: tag_value(tags, TAG_SIZE).and_then(|size| size.parse().ok()),
+            dim: tag_value(tags, TAG_DIM).and_then(parse_dim),
+            name: tag_value(tags, TAG_ALT).map(str::to_string),
+        })
+    }
+
+    pub fn is_image(&self) -> bool {
+        self.mime.starts_with("image/")
+    }
+
+    pub fn display_name(&self) -> SharedString {
+        if let Some(name) = &self.name {
+            return name.clone().into();
+        }
+
+        match self.size {
+            Some(size) => format!("{} ({size} bytes)", self.mime).into(),
+            None => self.mime.clone().into(),
+        }
+    }
+}
+
+pub fn encrypt(data: &[u8]) -> Result<EncryptedFile, Error> {
+    let key = Aes256Gcm::generate_key(OsRng);
+    let nonce = Aes256Gcm::generate_nonce(OsRng);
+    let cipher = Aes256Gcm::new(&key);
+
+    let data = cipher
+        .encrypt(&nonce, data)
+        .map_err(|_| anyhow!("Failed to encrypt file"))?;
+
+    Ok(EncryptedFile {
+        data,
+        key: STANDARD.encode(key.as_slice()),
+        nonce: STANDARD.encode(nonce.as_slice()),
+    })
+}
+
+pub fn decrypt(data: &[u8], key: &str, nonce: &str) -> Result<Vec<u8>, Error> {
+    let key = decode(key, 32, "decryption key")?;
+    let nonce = decode(nonce, 12, "decryption nonce")?;
+
+    let cipher = Aes256Gcm::new_from_slice(&key).map_err(|_| anyhow!("Invalid decryption key"))?;
+
+    cipher
+        .decrypt(Nonce::<U12>::from_slice(&nonce), data)
+        .map_err(|_| anyhow!("Failed to decrypt file"))
+}
+
+pub fn sha256_hex(data: &[u8]) -> String {
+    let hash: [u8; 32] = Sha256::digest(data).into();
+
+    Sha256Hash::from_byte_array(hash).to_hex()
+}
+
+#[cfg(not(target_arch = "wasm32"))]
+pub async fn upload_encrypted(
+    server: Url,
+    path: PathBuf,
+    cx: &AsyncApp,
+) -> Result<FileAttachment, Error> {
+    let mime = from_path(&path).first_or_octet_stream().to_string();
+    let name = path
+        .file_name()
+        .map(|name| name.to_string_lossy().into_owned());
+    let data = smol::fs::read(&path).await?;
+
+    let encrypted = encrypt(&data)?;
+    let sha256 = Some(sha256_hex(&encrypted.data));
+    let original_sha256 = Some(sha256_hex(&data));
+    let size = Some(encrypted.data.len() as u64);
+    let keys = Keys::generate();
+    let client = BlossomClient::new(server);
+
+    let url = Tokio::spawn(cx, async move {
+        let blob = client
+            .upload_blob(
+                encrypted.data,
+                Some("application/octet-stream".to_string()),
+                None,
+                Some(&keys),
+            )
+            .await?;
+
+        Ok::<Url, Error>(blob.url)
+    })
+    .await
+    .map_err(|e| anyhow!("Upload error: {e}"))??;
+
+    Ok(FileAttachment {
+        url,
+        mime,
+        key: encrypted.key,
+        nonce: encrypted.nonce,
+        sha256,
+        original_sha256,
+        size,
+        dim: None,
+        name,
+    })
+}
+
+#[cfg(target_arch = "wasm32")]
+pub async fn upload_encrypted(
+    _server: Url,
+    _path: PathBuf,
+    _cx: &AsyncApp,
+) -> Result<FileAttachment, Error> {
+    Err(anyhow!("File upload not supported on web"))
+}
+
+pub async fn download_and_decrypt(
+    url: &Url,
+    key: &str,
+    nonce: &str,
+    expected_sha256: Option<&str>,
+    cx: &AsyncApp,
+) -> Result<Vec<u8>, Error> {
+    let client = cx.update(|app| app.http_client());
+    let response = client.get(url.as_str(), AsyncBody::default(), true).await?;
+
+    if !response.status().is_success() {
+        bail!("Failed to download file: HTTP {}", response.status());
+    }
+
+    let mut data = Vec::new();
+    response
+        .into_body()
+        .take(MAX_FILE_SIZE as u64 + 1)
+        .read_to_end(&mut data)
+        .await?;
+
+    if data.len() > MAX_FILE_SIZE {
+        bail!("File is too large (max {MAX_FILE_SIZE} bytes)");
+    }
+
+    if let Some(expected) = expected_sha256
+        && !sha256_hex(&data).eq_ignore_ascii_case(expected)
+    {
+        bail!("File hash mismatch");
+    }
+
+    decrypt(&data, key, nonce)
+}
+
+fn tag_value<'a>(tags: &'a Tags, name: &str) -> Option<&'a str> {
+    tags.iter()
+        .find(|tag| tag.kind() == name)
+        .and_then(|tag| tag.content())
+}
+
+fn parse_dim(value: &str) -> Option<(u32, u32)> {
+    let (width, height) = value.split_once('x')?;
+
+    Some((width.parse().ok()?, height.parse().ok()?))
+}
+
+fn decode(value: &str, expected_len: usize, label: &str) -> Result<Vec<u8>, Error> {
+    let decoded = STANDARD
+        .decode(value)
+        .or_else(|_| STANDARD_NO_PAD.decode(value))
+        .or_else(|_| URL_SAFE.decode(value))
+        .or_else(|_| URL_SAFE_NO_PAD.decode(value))
+        .map_err(|_| anyhow!("Invalid {label} encoding"))?;
+
+    if decoded.len() != expected_len {
+        bail!(
+            "Invalid {label} length: expected {expected_len} bytes, got {}",
+            decoded.len()
+        );
+    }
+
+    Ok(decoded)
+}

crates/state/src/lib.rs

@@ -17,12 +17,14 @@ use nostr_sdk::prelude::*;
 
 mod blossom;
 mod constants;
+mod file;
 mod nip05;
 mod nip4e;
 mod signer;
 
 pub use blossom::*;
 pub use constants::*;
+pub use file::*;
 pub use nip4e::*;
 pub use nip05::*;
 pub use signer::{CoopAuthUrlHandler, UniversalSigner};