Add a manual workflow that runs the SDK live integration tests

.env.template

@@ -410,6 +410,12 @@
 ## - "biometrics-sdk-ipc": Enable biometric unlock over the SDK IPC framework (Desktop >= 2026.9.0, Browser >= 2026.9.0)
 ## - "windows-native-credential-sync": Register the desktop app as a passkey provider in Windows, so passkeys in the vault can be used by other apps and browsers.
 ##   Requires the Microsoft Store (appx) build of the desktop app. Stable releases up to and including 2026.9.1 lack the required plugin registration, so it has no effect there yet.
+## - "pm-27278-v2-password-registration": Register new accounts with v2 encryption. (Web >= 2026.6.4, Desktop/Browser/CLI >= 2026.7.0, Android >= 2026.4.1, iOS >= 2026.5.1)
+## - "enable-account-encryption-v2-jit-password-registration": Give SSO users who set their master password on their first login v2 encryption. (Web >= 2026.1.1, Desktop/Browser/CLI >= 2026.1.0, Android >= 2026.4.1, iOS >= 2026.6.0)
+## - "force-upgrade-v2-encryption": Upgrade every v1 account to v2 encryption the next time it's unlocked in a web, desktop, browser or CLI client. (Web >= 2026.6.4, Desktop/Browser/CLI >= 2026.7.0)
+##   These three flags can't be undone: a v2 account stays v2, and it can only log in from clients that are 2025.11.0 or newer and send their version, which rules out some older and third-party clients.
+## - "pm-30144-sdk-key-rotation": Only for clients up to 2026.10.0 (Desktop up to 2026.10.1): together with "force-upgrade-v2-encryption", a manual key rotation also upgrades a v1 account to v2.
+## - "pm-31050-no-logout-key-upgrade-rotation": Only for clients 2026.6.0 to 2026.10.0 (Desktop up to 2026.10.1): sync instead of logging out after the upgrade to v2. Newer clients always do.
 # EXPERIMENTAL_CLIENT_FEATURE_FLAGS=
 
 ## Require new device emails. When a user logs in an email is required to be sent.

.github/workflows/sdk-live-tests.yml

@@ -0,0 +1,65 @@
+name: SDK live tests
+permissions: {}
+
+# Runs the live-server integration tests of bitwarden/sdk-internal against this branch.
+# Only started by hand: it builds the SDK too, and the tests aren't in a released SDK yet.
+on:
+  workflow_dispatch:
+    inputs:
+      sdk_ref:
+        description: "Branch, tag or commit of bitwarden/sdk-internal to test with"
+        required: true
+        default: "km/live-server-integration-tests"
+
+defaults:
+  run:
+    shell: bash
+
+jobs:
+  sdk-live-tests:
+    name: SDK live tests
+    runs-on: ubuntu-24.04
+    timeout-minutes: 90
+    steps:
+      - name: "Install dependencies Ubuntu"
+        run: sudo apt-get update && sudo apt-get install -y --no-install-recommends build-essential libssl-dev pkg-config
+
+      - name: "Checkout"
+        uses: actions/checkout@3d3c42e5aac5ba805825da76410c181273ba90b1 # v7.0.1
+        with:
+          persist-credentials: false
+
+      - name: "Checkout sdk-internal"
+        uses: actions/checkout@3d3c42e5aac5ba805825da76410c181273ba90b1 # v7.0.1
+        with:
+          repository: bitwarden/sdk-internal
+          ref: ${{ inputs.sdk_ref }}
+          path: sdk-internal
+          persist-credentials: false
+
+      # Each checkout pins its own toolchain in rust-toolchain.toml
+      - name: "Install toolchains"
+        run: |
+          rustup toolchain install
+          cd sdk-internal
+          rustup toolchain install
+          rustup target add wasm32-unknown-unknown
+          rustup component add rust-src
+
+      - name: "Setup Node"
+        uses: actions/setup-node@820762786026740c76f36085b0efc47a31fe5020 # v7.0.0
+        with:
+          node-version: 20
+
+      - name: "Install binaryen"
+        run: npm i -g binaryen@132.0.0
+
+      - name: "Run the SDK live tests"
+        run: tools/sdk-live-tests/run.sh --sdk-dir sdk-internal
+
+      - name: "Upload logs"
+        if: ${{ failure() }}
+        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        with:
+          name: sdk-live-tests-logs
+          path: target/sdk-live-tests/**/*.log

.typos.toml

@@ -14,9 +14,8 @@ extend-ignore-re = [
     # In SMTP it's called HELO, so ignore it
     "(?i)helo_name",
     "Server name sent during.+HELO",
-    # COSE Is short for CBOR Object Signing and Encryption, ignore these specific items
+    # COSE Is short for CBOR Object Signing and Encryption
-    "COSEKey",
+    "(?i)cose",
-    "COSEAlgorithm",
     # Ignore this specific string as it's valid
     "Ensure they are valid OTPs",
     # This word is misspelled upstream

Cargo.toml

@@ -107,7 +107,7 @@ serde = { version = "1.0.229", features = ["derive"] }
 serde_json = "1.0.154"
 
 # A safe, extensible ORM and Query builder
-diesel = { version = "2.3.14", features = ["chrono", "r2d2", "numeric"] }
+diesel = { version = "2.3.14", features = ["chrono", "r2d2", "numeric", "64-column-tables"] }
 diesel_migrations = "2.3.2"
 
 derive_more = { version = "2.1.1", features = [

migrations/mysql/2026-10-09-120000_user_crypto_v2/down.sql

@@ -0,0 +1,5 @@
+DROP TABLE IF EXISTS user_signature_key_pairs;
+
+ALTER TABLE users DROP COLUMN signed_public_key;
+ALTER TABLE users DROP COLUMN security_state;
+ALTER TABLE users DROP COLUMN security_version;

migrations/mysql/2026-10-09-120000_user_crypto_v2/up.sql

@@ -0,0 +1,14 @@
+ALTER TABLE users ADD COLUMN signed_public_key TEXT;
+ALTER TABLE users ADD COLUMN security_state TEXT;
+ALTER TABLE users ADD COLUMN security_version INTEGER;
+
+CREATE TABLE user_signature_key_pairs (
+    uuid                CHAR(36) NOT NULL PRIMARY KEY,
+    user_uuid           CHAR(36) NOT NULL UNIQUE,
+    signature_algorithm INTEGER  NOT NULL, -- 0 = ed25519, 1 = mldsa44
+    signing_key         TEXT     NOT NULL,
+    verifying_key       TEXT     NOT NULL,
+    created_at          DATETIME NOT NULL,
+    updated_at          DATETIME NOT NULL,
+    FOREIGN KEY (user_uuid) REFERENCES users (uuid) ON DELETE CASCADE
+);

migrations/mysql/2026-10-10-120000_add_v2_upgrade_token/down.sql

@@ -0,0 +1,2 @@
+ALTER TABLE users DROP COLUMN v2_upgrade_token;
+ALTER TABLE users_organizations DROP COLUMN v2_upgrade_token;

migrations/mysql/2026-10-10-120000_add_v2_upgrade_token/up.sql

@@ -0,0 +1,2 @@
+ALTER TABLE users ADD COLUMN v2_upgrade_token TEXT;
+ALTER TABLE users_organizations ADD COLUMN v2_upgrade_token TEXT;

migrations/mysql/2026-11-02-120000_reset_user_key_id/up.sql

@@ -0,0 +1,4 @@
+-- Key rotations before this kept the id of the old user key, so every new
+-- cipher was refused from then on. Stale ids can't be told apart, so clear
+-- all of them; clients record their current key's id again when it's empty.
+UPDATE users SET key_id = NULL;

migrations/postgresql/2026-10-09-120000_user_crypto_v2/down.sql

@@ -0,0 +1,5 @@
+DROP TABLE IF EXISTS user_signature_key_pairs;
+
+ALTER TABLE users DROP COLUMN signed_public_key;
+ALTER TABLE users DROP COLUMN security_state;
+ALTER TABLE users DROP COLUMN security_version;

migrations/postgresql/2026-10-09-120000_user_crypto_v2/up.sql

@@ -0,0 +1,13 @@
+ALTER TABLE users ADD COLUMN signed_public_key TEXT;
+ALTER TABLE users ADD COLUMN security_state TEXT;
+ALTER TABLE users ADD COLUMN security_version INTEGER;
+
+CREATE TABLE user_signature_key_pairs (
+    uuid                CHAR(36) NOT NULL PRIMARY KEY,
+    user_uuid           CHAR(36) NOT NULL UNIQUE REFERENCES users (uuid) ON DELETE CASCADE,
+    signature_algorithm INTEGER  NOT NULL, -- 0 = ed25519, 1 = mldsa44
+    signing_key         TEXT     NOT NULL,
+    verifying_key       TEXT     NOT NULL,
+    created_at          TIMESTAMP NOT NULL,
+    updated_at          TIMESTAMP NOT NULL
+);

migrations/postgresql/2026-10-10-120000_add_v2_upgrade_token/down.sql

@@ -0,0 +1,2 @@
+ALTER TABLE users DROP COLUMN v2_upgrade_token;
+ALTER TABLE users_organizations DROP COLUMN v2_upgrade_token;

migrations/postgresql/2026-10-10-120000_add_v2_upgrade_token/up.sql

@@ -0,0 +1,2 @@
+ALTER TABLE users ADD COLUMN v2_upgrade_token TEXT;
+ALTER TABLE users_organizations ADD COLUMN v2_upgrade_token TEXT;

migrations/postgresql/2026-11-02-120000_reset_user_key_id/up.sql

@@ -0,0 +1,4 @@
+-- Key rotations before this kept the id of the old user key, so every new
+-- cipher was refused from then on. Stale ids can't be told apart, so clear
+-- all of them; clients record their current key's id again when it's empty.
+UPDATE users SET key_id = NULL;

migrations/sqlite/2026-10-09-120000_user_crypto_v2/down.sql

@@ -0,0 +1,5 @@
+DROP TABLE IF EXISTS user_signature_key_pairs;
+
+ALTER TABLE users DROP COLUMN signed_public_key;
+ALTER TABLE users DROP COLUMN security_state;
+ALTER TABLE users DROP COLUMN security_version;

migrations/sqlite/2026-10-09-120000_user_crypto_v2/up.sql

@@ -0,0 +1,13 @@
+ALTER TABLE users ADD COLUMN signed_public_key TEXT;
+ALTER TABLE users ADD COLUMN security_state TEXT;
+ALTER TABLE users ADD COLUMN security_version INTEGER;
+
+CREATE TABLE user_signature_key_pairs (
+    uuid                TEXT     NOT NULL PRIMARY KEY,
+    user_uuid           TEXT     NOT NULL UNIQUE REFERENCES users (uuid) ON DELETE CASCADE,
+    signature_algorithm INTEGER  NOT NULL, -- 0 = ed25519, 1 = mldsa44
+    signing_key         TEXT     NOT NULL,
+    verifying_key       TEXT     NOT NULL,
+    created_at          DATETIME NOT NULL,
+    updated_at          DATETIME NOT NULL
+);

migrations/sqlite/2026-10-10-120000_add_v2_upgrade_token/down.sql

@@ -0,0 +1,2 @@
+ALTER TABLE users DROP COLUMN v2_upgrade_token;
+ALTER TABLE users_organizations DROP COLUMN v2_upgrade_token;

migrations/sqlite/2026-10-10-120000_add_v2_upgrade_token/up.sql

@@ -0,0 +1,2 @@
+ALTER TABLE users ADD COLUMN v2_upgrade_token TEXT;
+ALTER TABLE users_organizations ADD COLUMN v2_upgrade_token TEXT;

migrations/sqlite/2026-11-02-120000_reset_user_key_id/up.sql

@@ -0,0 +1,4 @@
+-- Key rotations before this kept the id of the old user key, so every new
+-- cipher was refused from then on. Stale ids can't be told apart, so clear
+-- all of them; clients record their current key's id again when it's empty.
+UPDATE users SET key_id = NULL;

src/api/admin.rs

@@ -430,7 +430,7 @@ async fn delete_user(user_id: UserId, token: AdminToken, conn: DbConn, nt: Notif
     if res.is_ok() {
         nt.send_logout(&user, None, &conn).await;
         if has_push_device {
-            push_logout_to_relay(&user, None);
+            push_logout_to_relay(&user, None, None);
         }
     }
 

src/api/core/ciphers.rs

@@ -190,7 +190,7 @@ async fn sync(data: SyncData, headers: Headers, client_version: Option<ClientVer
             // https://github.com/bitwarden/android/blob/release/2025.12-rc41/network/src/main/kotlin/com/bitwarden/network/model/MasterPasswordUnlockDataJson.kt#L22-L26
             "masterKeyEncryptedUserKey": headers.user.akey,
             "masterKeyWrappedUserKey": headers.user.akey,
-            "salt": headers.user.email,
+            "salt": headers.user.master_password_salt(),
             "containedKeyId": headers.user.key_id,
         })
     } else {
@@ -202,6 +202,9 @@ async fn sync(data: SyncData, headers: Headers, client_version: Option<ClientVer
     if let Some(key_id) = &headers.user.key_id {
         user_decryption["userKeyId"] = json!(key_id);
     }
+    if let Some(v2_upgrade_token) = headers.user.v2_upgrade_token_json() {
+        user_decryption["v2UpgradeToken"] = v2_upgrade_token;
+    }
 
     Ok(Json(json!({
         "profile": user_json,
@@ -563,6 +566,40 @@ pub async fn update_cipher_from_data(
     conn: &DbConn,
     nt: &Notify<'_>,
     ut: UpdateType,
+) -> EmptyResult {
+    enforce_personal_ownership_policy(Some(&data), headers, conn).await?;
+    save_cipher_data(cipher, data, headers, shared_to_collections, conn, nt, ut).await
+}
+
+/// [`update_cipher_from_data`] for a rotation: like upstream, the personal ownership policy doesn't apply.
+pub async fn rotate_cipher_data(
+    cipher: &mut Cipher,
+    data: CipherData,
+    headers: &Headers,
+    conn: &DbConn,
+    nt: &Notify<'_>,
+) -> EmptyResult {
+    save_cipher_data(cipher, data, headers, None, conn, nt, UpdateType::None).await
+}
+
+/// The checks of [`rotate_cipher_data`] that need the database, to run on every cipher before the first is saved
+pub async fn validate_rotated_cipher(
+    cipher: &Cipher,
+    data: &CipherData,
+    headers: &Headers,
+    conn: &DbConn,
+) -> EmptyResult {
+    validate_cipher_update(cipher, data, headers, conn, UpdateType::None).await
+}
+
+async fn save_cipher_data(
+    cipher: &mut Cipher,
+    data: CipherData,
+    headers: &Headers,
+    shared_to_collections: Option<Vec<CollectionId>>,
+    conn: &DbConn,
+    nt: &Notify<'_>,
+    ut: UpdateType,
 ) -> EmptyResult {
     // Cleanup cipher data, like removing the 'Response' key.
     // This key is somewhere generated during Javascript so no way for us this fix this.
@@ -578,8 +615,6 @@ pub async fn update_cipher_from_data(
         json_data
     }
 
-    enforce_personal_ownership_policy(Some(&data), headers, conn).await?;
-
     let is_blob = data.is_blob();
     data.validate_content(is_blob)?;
     data.validate_type_data(is_blob)?;

src/api/core/organizations.rs

@@ -8,7 +8,7 @@ use crate::{
     CONFIG,
     api::admin::FAKE_ADMIN_UUID,
     api::{
-        EmptyResult, JsonResult, Notify, PasswordOrOtpData, UpdateType,
+        ApiResult, EmptyResult, JsonResult, Notify, PasswordOrOtpData, UpdateType,
         core::{CipherSyncData, CipherSyncType, accept_org_invite, log_event, two_factor},
     },
     auth::{AdminHeaders, Headers, ManagerHeaders, ManagerHeadersLoose, OrgMemberHeaders, OwnerHeaders, decode_invite},
@@ -2849,8 +2849,26 @@ struct OrganizationUserRecoverAccountRequest {
 // But the clients do not seem to use this at all
 // Just add it here in case they will
 #[get("/organizations/<org_id>/public-key")]
-async fn get_organization_public_key(org_id: OrganizationId, headers: OrgMemberHeaders, conn: DbConn) -> JsonResult {
+async fn get_organization_public_key(
-    if org_id != headers.membership.org_uuid {
+    org_id: OrganizationId,
+    headers: Headers,
+    member: Result<OrgMemberHeaders, &'static str>,
+    conn: DbConn,
+) -> JsonResult {
+    // SSO users without an org get the fake one, whose key the v2 JIT password flow fetches anyway
+    if org_id.eq_ignore_ascii_case(FAKE_SSO_IDENTIFIER) && headers.user.private_key.is_none() {
+        return Ok(Json(json!({
+            "object": "organizationPublicKey",
+            "publicKey": fake_sso_org_public_key().await?,
+        })));
+    }
+    let member = match member {
+        Ok(member) => member,
+        // The guard already logged it
+        Err(e) => return Err(crate::error::Error::new_msg(e).with_code(Status::Unauthorized.code)),
+    };
+
+    if org_id != member.membership.org_uuid {
         err!("Organization not found", "Organization id's do not match");
     }
     let Some(org) = Organization::find_by_uuid(&org_id, &conn).await else {
@@ -2863,11 +2881,30 @@ async fn get_organization_public_key(org_id: OrganizationId, headers: OrgMemberH
     })))
 }
 
+/// The SDK only uses this key to wrap an account recovery key that it never sends for the fake org,
+/// so it is made once and its private half dropped.
+async fn fake_sso_org_public_key() -> ApiResult<String> {
+    static PUBLIC_KEY: std::sync::LazyLock<Option<String>> = std::sync::LazyLock::new(|| {
+        let der = openssl::rsa::Rsa::generate(2048).and_then(|rsa| rsa.public_key_to_der()).ok()?;
+        Some(data_encoding::BASE64.encode(&der))
+    });
+
+    let Ok(Some(public_key)) = tokio::task::spawn_blocking(|| PUBLIC_KEY.clone()).await else {
+        err!("Failed to generate the organization key")
+    };
+    Ok(public_key)
+}
+
 // Obsolete - Renamed to public-key (2023.8), left for backwards compatibility with older clients
 // https://github.com/bitwarden/server/blob/9ebe16587175b1c0e9208f84397bb75d0d595510/src/Api/AdminConsole/Controllers/OrganizationsController.cs#L487-L492
 #[get("/organizations/<org_id>/keys")]
-async fn get_organization_keys(org_id: OrganizationId, headers: OrgMemberHeaders, conn: DbConn) -> JsonResult {
+async fn get_organization_keys(
-    get_organization_public_key(org_id, headers, conn).await
+    org_id: OrganizationId,
+    headers: Headers,
+    member: Result<OrgMemberHeaders, &'static str>,
+    conn: DbConn,
+) -> JsonResult {
+    get_organization_public_key(org_id, headers, member, conn).await
 }
 
 // Will allow to reset 2FA too

src/api/identity.rs

@@ -77,14 +77,14 @@ async fn login(data: Form<ConnectData>, client_header: ClientHeaders, conn: DbCo
             check_is_some(data.device_name.as_ref(), "device_name cannot be blank")?;
             check_is_some(data.device_type.as_ref(), "device_type cannot be blank")?;
 
-            password_login(data, &mut user_id, &conn, &client_header.ip).await
+            password_login(data, &mut user_id, &conn, &client_header.ip, client_header.client_version.as_ref()).await
         }
         "client_credentials" => {
             check_is_some(data.client_id.as_ref(), "client_id cannot be blank")?;
             check_is_some(data.client_secret.as_ref(), "client_secret cannot be blank")?;
             check_is_some(data.scope.as_ref(), "scope cannot be blank")?;
 
-            api_key_login(data, &mut user_id, &conn, &client_header.ip).await
+            api_key_login(data, &mut user_id, &conn, &client_header.ip, client_header.client_version.as_ref()).await
         }
         "authorization_code" if CONFIG.sso_enabled() => {
             check_is_some(data.client_id.as_ref(), "client_id cannot be blank")?;
@@ -95,7 +95,7 @@ async fn login(data: Form<ConnectData>, client_header: ClientHeaders, conn: DbCo
             check_is_some(data.device_name.as_ref(), "device_name cannot be blank")?;
             check_is_some(data.device_type.as_ref(), "device_type cannot be blank")?;
 
-            sso_login(data, &mut user_id, &conn, &client_header.ip).await
+            sso_login(data, &mut user_id, &conn, &client_header.ip, client_header.client_version.as_ref()).await
         }
         "authorization_code" => err!("SSO sign-in is not available"),
         "send_access" => {
@@ -179,7 +179,13 @@ async fn refresh_login(data: ConnectData, conn: &DbConn, ip: &ClientIp) -> JsonR
 }
 
 // After exchanging the code we need to check first if 2FA is needed before continuing
-async fn sso_login(data: ConnectData, user_id: &mut Option<UserId>, conn: &DbConn, ip: &ClientIp) -> JsonResult {
+async fn sso_login(
+    data: ConnectData,
+    user_id: &mut Option<UserId>,
+    conn: &DbConn,
+    ip: &ClientIp,
+    client_version: Option<&semver::Version>,
+) -> JsonResult {
     AuthMethod::Sso.check_scope(data.scope.as_ref())?;
 
     // Ratelimit the login
@@ -325,6 +331,8 @@ async fn sso_login(data: ConnectData, user_id: &mut Option<UserId>, conn: &DbCon
             (user, device, None, None)
         }
         Some((user, _)) if !user.enabled => {
+            // Set in both arms, not only after the match, so that their failed logins are logged
+            *user_id = Some(user.uuid.clone());
             err!(
                 "This user has been disabled",
                 format!("IP: {}. Username: {}.", ip.ip, user.email),
@@ -334,6 +342,9 @@ async fn sso_login(data: ConnectData, user_id: &mut Option<UserId>, conn: &DbCon
             )
         }
         Some((mut user, sso_user)) => {
+            *user_id = Some(user.uuid.clone());
+            check_client_version(&user, client_version, ip)?;
+
             let mut device = get_device(&data, conn, &user).await?;
 
             let twofactor_token = twofactor_auth(&mut user, &data, &mut device, ip, conn).await?;
@@ -368,7 +379,13 @@ async fn sso_login(data: ConnectData, user_id: &mut Option<UserId>, conn: &DbCon
     authenticated_response(&user, &mut device, auth_tokens, twofactor_token, conn, ip).await
 }
 
-async fn password_login(data: ConnectData, user_id: &mut Option<UserId>, conn: &DbConn, ip: &ClientIp) -> JsonResult {
+async fn password_login(
+    data: ConnectData,
+    user_id: &mut Option<UserId>,
+    conn: &DbConn,
+    ip: &ClientIp,
+    client_version: Option<&semver::Version>,
+) -> JsonResult {
     // Validate scope
     AuthMethod::Password.check_scope(data.scope.as_ref())?;
 
@@ -438,6 +455,8 @@ async fn password_login(data: ConnectData, user_id: &mut Option<UserId>, conn: &
         )
     }
 
+    check_client_version(&user, client_version, ip)?;
+
     // Change the KDF Iterations (only when not logging in with an auth request)
     if data.auth_request.is_none() {
         kdf_upgrade(&mut user, password, conn).await?;
@@ -499,6 +518,47 @@ async fn password_login(data: ConnectData, user_id: &mut Option<UserId>, conn: &
     authenticated_response(&user, &mut device, auth_tokens, twofactor_token, conn, ip).await
 }
 
+/// Like upstream's `ClientVersionValidator`, a V2 account ([`User::has_v2_encryption`]) logs in only from a client that
+/// sends its version and is at least 2025.11.0 (upstream also refuses a missing header for V1 accounts). Called right
+/// after the credentials are checked, like upstream, so that it doesn't tell anyone else which accounts are V2.
+///
+/// Ref: <https://github.com/bitwarden/server/blob/8da186ad73f80d37157fe6fd42323e4284e83ec1/src/Identity/IdentityServer/RequestValidators/ClientVersionValidator.cs#L31-L72>
+fn check_client_version(user: &User, client_version: Option<&semver::Version>, ip: &ClientIp) -> EmptyResult {
+    let Some((error, description)) = client_version_error(user.has_v2_encryption(), client_version) else {
+        return Ok(());
+    };
+    Err(crate::error::Error::from((
+        format!("IP: {}. Username: {}. {error}", ip.ip, user.email),
+        json!({
+            "error": error,
+            "error_description": description,
+            "ErrorModel": { "Message": description, "Object": "error" },
+        }),
+    ))
+    .with_event(crate::error::ErrorEvent {
+        event: EventType::UserFailedLogIn,
+    }))
+}
+
+/// The error id and message of [`check_client_version`], `None` when the client may log in.
+fn client_version_error(is_v2: bool, client_version: Option<&semver::Version>) -> Option<(&'static str, &'static str)> {
+    const MIN_V2_CLIENT: semver::Version = semver::Version::new(2025, 11, 0);
+
+    if !is_v2 {
+        return None;
+    }
+    match client_version {
+        None => Some((
+            "version_header_missing",
+            "No client version header found, required to prevent encryption errors. Please confirm your client is supplying the header: \"Bitwarden-Client-Version\"",
+        )),
+        Some(version) if *version < MIN_V2_CLIENT => {
+            Some(("invalid_client_version", "Please update your app to continue using Bitwarden"))
+        }
+        Some(_) => None,
+    }
+}
+
 async fn authenticated_response(
     user: &User,
     device: &mut Device,
@@ -546,24 +606,13 @@ async fn authenticated_response(
             // https://github.com/bitwarden/android/blob/release/2025.12-rc41/network/src/main/kotlin/com/bitwarden/network/model/MasterPasswordUnlockDataJson.kt#L22-L26
             "MasterKeyEncryptedUserKey": user.akey,
             "MasterKeyWrappedUserKey": user.akey,
-            "Salt": user.email
+            "Salt": user.master_password_salt()
         })
     } else {
         Value::Null
     };
 
-    let account_keys = if user.private_key.is_some() {
+    let account_keys = user.account_keys_json(conn).await;
-        json!({
-            "publicKeyEncryptionKeyPair": {
-                "wrappedPrivateKey": user.private_key,
-                "publicKey": user.public_key,
-                "Object": "publicKeyEncryptionKeyPair"
-            },
-            "Object": "privateKeys"
-        })
-    } else {
-        Value::Null
-    };
 
     let mut result = json!({
         "access_token": auth_tokens.access_token(),
@@ -598,7 +647,13 @@ async fn authenticated_response(
     Ok(Json(result))
 }
 
-async fn api_key_login(data: ConnectData, user_id: &mut Option<UserId>, conn: &DbConn, ip: &ClientIp) -> JsonResult {
+async fn api_key_login(
+    data: ConnectData,
+    user_id: &mut Option<UserId>,
+    conn: &DbConn,
+    ip: &ClientIp,
+    client_version: Option<&semver::Version>,
+) -> JsonResult {
     // Ratelimit the login
     crate::ratelimit::check_limit_login(&ip.ip)?;
 
@@ -610,7 +665,7 @@ async fn api_key_login(data: ConnectData, user_id: &mut Option<UserId>, conn: &D
             check_is_some(data.device_name.as_ref(), "device_name cannot be blank")?;
             check_is_some(data.device_type.as_ref(), "device_type cannot be blank")?;
 
-            user_api_key_login(data, user_id, conn, ip).await
+            user_api_key_login(data, user_id, conn, ip, client_version).await
         }
         Some(scope) if scope == &AuthMethod::OrgApiKey.scope() => organization_api_key_login(data, conn, ip).await,
         _ => err!("Scope not supported"),
@@ -622,6 +677,7 @@ async fn user_api_key_login(
     user_id: &mut Option<UserId>,
     conn: &DbConn,
     ip: &ClientIp,
+    client_version: Option<&semver::Version>,
 ) -> JsonResult {
     // Get the user via the client_id
     let client_id = data.client_id.as_ref().unwrap();
@@ -659,6 +715,8 @@ async fn user_api_key_login(
         )
     }
 
+    check_client_version(&user, client_version, ip)?;
+
     let mut device = get_device(&data, conn, &user).await?;
 
     if CONFIG.mail_enabled() && device.is_new() {
@@ -703,24 +761,13 @@ async fn user_api_key_login(
             // https://github.com/bitwarden/android/blob/release/2025.12-rc41/network/src/main/kotlin/com/bitwarden/network/model/MasterPasswordUnlockDataJson.kt#L22-L26
             "MasterKeyEncryptedUserKey": user.akey,
             "MasterKeyWrappedUserKey": user.akey,
-            "Salt": user.email
+            "Salt": user.master_password_salt()
         })
     } else {
         Value::Null
     };
 
-    let account_keys = if user.private_key.is_some() {
+    let account_keys = user.account_keys_json(conn).await;
-        json!({
-            "publicKeyEncryptionKeyPair": {
-                "wrappedPrivateKey": user.private_key,
-                "publicKey": user.public_key,
-                "Object": "publicKeyEncryptionKeyPair"
-            },
-            "Object": "privateKeys"
-        })
-    } else {
-        Value::Null
-    };
 
     // Note: No refresh_token is returned. The CLI just repeats the
     // client_credentials login flow when the existing token expires.
@@ -1351,3 +1398,24 @@ async fn authorize(data: AuthorizeData, cookies: &CookieJar<'_>, secure: Secure,
 
     Ok(Redirect::temporary(String::from(auth_url)))
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_client_version_error() {
+        let version = |v| semver::Version::parse(v).unwrap();
+        // V1 accounts aren't checked, with or without a version
+        assert_eq!(client_version_error(false, None), None);
+        assert_eq!(client_version_error(false, Some(&version("2024.1.0"))), None);
+        // V2 accounts need the header and 2025.11.0 or newer
+        assert_eq!(client_version_error(true, None).map(|e| e.0), Some("version_header_missing"));
+        assert_eq!(
+            client_version_error(true, Some(&version("2025.10.3"))).map(|e| e.0),
+            Some("invalid_client_version")
+        );
+        assert_eq!(client_version_error(true, Some(&version("2025.11.0"))), None);
+        assert_eq!(client_version_error(true, Some(&version("2026.10.1"))), None);
+    }
+}

src/api/mod.rs

@@ -23,7 +23,7 @@ pub use crate::api::{
     icons::routes as icons_routes,
     identity::routes as identity_routes,
     notifications::routes as notifications_routes,
-    notifications::{AnonymousNotify, Notify, UpdateType, WS_ANONYMOUS_SUBSCRIPTIONS, WS_USERS},
+    notifications::{AnonymousNotify, LogOutReason, Notify, UpdateType, WS_ANONYMOUS_SUBSCRIPTIONS, WS_USERS},
     push::{
         push_cipher_update, push_folder_update, push_logout, push_logout_to_relay, push_send_update, push_user_update,
         register_push_device, unregister_push_device,

src/api/notifications.rs

@@ -412,23 +412,35 @@ impl WebSocketUsers {
     }
 
     pub async fn send_logout(&self, user: &User, acting_device: Option<&Device>, conn: &DbConn) {
+        self.send_logout_with_reason(user, acting_device, None, conn).await;
+    }
+
+    /// A logout that clients may handle differently depending on `reason`
+    pub async fn send_logout_with_reason(
+        &self,
+        user: &User,
+        acting_device: Option<&Device>,
+        reason: Option<LogOutReason>,
+        conn: &DbConn,
+    ) {
         // Skip any processing if both WebSockets and Push are not active
         if *NOTIFICATIONS_DISABLED {
             return;
         }
         let acting_device_id = acting_device.map(|d| d.uuid.clone());
-        let data = create_update(
+        let mut payload =
-            vec![("UserId".into(), user.uuid.to_string().into()), ("Date".into(), serialize_date(user.updated_at))],
+            vec![("UserId".into(), user.uuid.to_string().into()), ("Date".into(), serialize_date(user.updated_at))];
-            UpdateType::LogOut,
+        if let Some(reason) = reason {
-            acting_device_id,
+            payload.push(("Reason".into(), (reason as i32).into()));
-        );
+        }
+        let data = create_update(payload, UpdateType::LogOut, acting_device_id);
 
         if CONFIG.enable_websocket() {
             self.send_update(&user.uuid, &data).await;
         }
 
         if CONFIG.push_enabled() {
-            push_logout(user, acting_device, conn).await;
+            push_logout(user, acting_device, reason, conn).await;
         }
     }
 
@@ -692,6 +704,14 @@ fn create_anonymous_update(payload: Vec<(Value, Value)>, ut: UpdateType, user_id
     serialize(&value)
 }
 
+/// Why a logout was pushed, absent for a plain one. `KdfChange` isn't sent yet.
+///
+/// Ref: <https://github.com/bitwarden/server/blob/9030c42bf7d8f9ac2ff9fee85c39588d5eb81499/src/Core/Enums/PushNotificationLogOutReason.cs#L3-L7>
+#[derive(Copy, Clone, Eq, PartialEq)]
+pub enum LogOutReason {
+    KeyRotation = 1,
+}
+
 // https://github.com/bitwarden/server/blob/375af7c43b10d9da03525d41452f95de3f921541/src/Core/Enums/PushType.cs
 #[derive(Copy, Clone, Eq, PartialEq)]
 pub enum UpdateType {

src/api/push.rs

@@ -12,7 +12,7 @@ use tokio::sync::RwLock;
 
 use crate::{
     CONFIG,
-    api::{ApiResult, EmptyResult, UpdateType},
+    api::{ApiResult, EmptyResult, LogOutReason, UpdateType},
     db::{
         DbConn,
         models::{AuthRequestId, Cipher, Device, Folder, PushId, Send, User, UserId},
@@ -192,15 +192,15 @@ pub async fn push_cipher_update(ut: UpdateType, cipher: &Cipher, device: &Device
     }
 }
 
-pub async fn push_logout(user: &User, acting_device: Option<&Device>, conn: &DbConn) {
+pub async fn push_logout(user: &User, acting_device: Option<&Device>, reason: Option<LogOutReason>, conn: &DbConn) {
     if Device::check_user_has_push_device(&user.uuid, conn).await {
-        push_logout_to_relay(user, acting_device);
+        push_logout_to_relay(user, acting_device, reason);
     }
 }
 
 // Sends the logout without checking for push devices first.
 // Needed after deleting a user, when the devices are already gone from the database.
-pub fn push_logout_to_relay(user: &User, acting_device: Option<&Device>) {
+pub fn push_logout_to_relay(user: &User, acting_device: Option<&Device>, reason: Option<LogOutReason>) {
     tokio::task::spawn(send_to_push_relay(json!({
         "userId": user.uuid,
         "organizationId": (),
@@ -209,7 +209,8 @@ pub fn push_logout_to_relay(user: &User, acting_device: Option<&Device>) {
         "type": UpdateType::LogOut as i32,
         "payload": {
             "userId": user.uuid,
-            "date": format_date(&user.updated_at)
+            "date": format_date(&user.updated_at),
+            "reason": reason.map(|r| r as i32),
         },
         "clientType": null,
         "installationId": null

src/auth.rs

@@ -34,7 +34,7 @@ use crate::{
         models::{
             AttachmentId, CipherId, Collection, CollectionId, Device, DeviceId, DeviceType, EmergencyAccessId,
             EventType, Membership, MembershipId, MembershipStatus, MembershipType, OrgApiKeyId, OrganizationId,
-            SendFileId, SendId, User, UserId, UserStampException,
+            SendFileId, SendId, User, UserId,
         },
     },
     error::Error,
@@ -632,6 +632,9 @@ impl<'r> FromRequest<'r> for Host {
 pub struct ClientHeaders {
     pub device_type: i32,
     pub ip: ClientIp,
+    /// `Bitwarden-Client-Version`, `None` when missing or not a version. Unlike the [`ClientVersion`] guard, this
+    /// doesn't log an error, as not every client sends it.
+    pub client_version: Option<semver::Version>,
 }
 
 #[rocket::async_trait]
@@ -648,10 +651,13 @@ impl<'r> FromRequest<'r> for ClientHeaders {
             .get_one("device-type")
             .and_then(|d| d.parse().ok())
             .unwrap_or(DeviceType::UnknownBrowser as i32);
+        let client_version =
+            request.headers().get_one("Bitwarden-Client-Version").and_then(|v| semver::Version::parse(v).ok());
 
         Outcome::Success(ClientHeaders {
             device_type,
             ip,
+            client_version,
         })
     }
 }
@@ -707,31 +713,12 @@ impl<'r> FromRequest<'r> for Headers {
         };
 
         if user.security_stamp != claims.sstamp {
-            if let Some(stamp_exception) =
-                user.stamp_exception.as_deref().and_then(|s| serde_json::from_str::<UserStampException>(s).ok())
-            {
             let Some(current_route) = request.route().and_then(|r| r.name.as_deref()) else {
                 err_handler!("Error getting current route for stamp exception")
             };
 
-                // Check if the stamp exception has expired first.
+            // Expired exceptions are only dropped on reset; writing them back here could undo a newer reset
-                // Then, check if the current route matches any of the allowed routes.
+            if !user.stamp_exceptions().iter().any(|e| e.allows(&claims.sstamp, current_route)) {
-                // After that check the stamp in exception matches the one in the claims.
-                if Utc::now().timestamp() > stamp_exception.expire {
-                    // If the stamp exception has been expired remove it from the database.
-                    // This prevents checking this stamp exception for new requests.
-                    let mut user = user;
-                    user.reset_stamp_exception();
-                    if let Err(e) = user.save(&conn).await {
-                        error!("Error updating user: {e:#?}");
-                    }
-                    err_handler!("Stamp exception is expired")
-                } else if !stamp_exception.routes.contains(&current_route.to_owned()) {
-                    err_handler!("Invalid security stamp: Current route and exception route do not match")
-                } else if stamp_exception.security_stamp != claims.sstamp {
-                    err_handler!("Invalid security stamp for matched stamp exception")
-                }
-            } else {
                 err_handler!("Invalid security stamp")
             }
         }

src/config.rs

@@ -1508,6 +1508,11 @@ pub const SUPPORTED_FEATURE_FLAGS: &[&str] = &[
     // Key Management Team
     "biometrics-sdk-ipc",
     "windows-native-credential-sync",
+    "pm-30144-sdk-key-rotation",
+    "pm-31050-no-logout-key-upgrade-rotation",
+    "enable-account-encryption-v2-jit-password-registration",
+    "pm-27278-v2-password-registration",
+    "force-upgrade-v2-encryption",
     // Mobile Team
     "pm-34171-card-scanner",
     // Platform Team

src/db/models/mod.rs

@@ -17,6 +17,7 @@ mod two_factor;
 mod two_factor_duo_context;
 mod two_factor_incomplete;
 mod user;
+mod user_signature_key_pair;
 
 pub use self::archive::Archive;
 pub use self::attachment::{Attachment, AttachmentId};
@@ -41,4 +42,5 @@ pub use self::sso_auth::{OIDCAuthenticatedUser, OIDCCodeResponseError, SsoAuth};
 pub use self::two_factor::{TwoFactor, TwoFactorType};
 pub use self::two_factor_duo_context::TwoFactorDuoContext;
 pub use self::two_factor_incomplete::TwoFactorIncomplete;
-pub use self::user::{Invitation, KeyId, SsoUser, User, UserId, UserKdfType, UserStampException};
+pub use self::user::{Invitation, KeyId, SsoUser, User, UserId, UserKdfType};
+pub use self::user_signature_key_pair::{SignatureAlgorithm, UserSignatureKeyPair};

src/db/models/organization.rs

@@ -54,6 +54,8 @@ pub struct Membership {
     pub atype: i32,
     pub reset_password_key: Option<String>,
     pub external_id: Option<String>,
+    /// The user's v2 upgrade token, for the org to unwrap the v2 user key after an upgrade. Opaque to us.
+    pub v2_upgrade_token: Option<String>,
 }
 
 #[derive(Identifiable, Queryable, Insertable, AsChangeset)]
@@ -271,6 +273,7 @@ impl Membership {
             atype: MembershipType::User as i32,
             reset_password_key: None,
             external_id: None,
+            v2_upgrade_token: None,
         }
     }
 

src/db/models/user.rs

@@ -6,6 +6,7 @@ use serde_json::Value;
 use crate::{
     CONFIG,
     api::EmptyResult,
+    auth::DEFAULT_ACCESS_VALIDITY,
     crypto,
     db::{
         DbConn,
@@ -20,7 +21,7 @@ use macros::UuidFromParam;
 
 use super::{
     AuthRequest, Cipher, Device, EmergencyAccess, Favorite, Folder, Membership, MembershipType, TwoFactor,
-    TwoFactorIncomplete,
+    TwoFactorIncomplete, UserSignatureKeyPair,
 };
 
 #[derive(Identifiable, Queryable, Insertable, AsChangeset, Selectable)]
@@ -72,6 +73,13 @@ pub struct User {
     pub external_id: Option<String>, // Todo: Needs to be removed in the future, this is not used anymore.
 
     pub key_id: Option<KeyId>,
+
+    // The v2 state: all set, with a `user_signature_key_pairs` row, or none, see `User::is_v2`
+    pub signed_public_key: Option<String>,
+    pub security_state: Option<String>,
+    pub security_version: Option<i32>,
+    /// JSON `{"wrappedUserKey1", "wrappedUserKey2"}` for sessions that still hold the v1 user key. Opaque to us.
+    pub v2_upgrade_token: Option<String>,
 }
 
 #[derive(Identifiable, Queryable, Insertable)]
@@ -100,13 +108,28 @@ enum UserStatus {
     _Disabled = 2,
 }
 
+/// A previous security stamp that is still accepted, until `expire`.
 #[derive(Serialize, Deserialize)]
 pub struct UserStampException {
-    pub routes: Vec<String>,
+    /// The routes the stamp is still accepted on, or `None` for any route.
+    pub routes: Option<Vec<String>>,
     pub security_stamp: String,
     pub expire: i64,
 }
 
+impl UserStampException {
+    pub fn is_expired(&self) -> bool {
+        Utc::now().timestamp() > self.expire
+    }
+
+    /// Whether this exception lets a token carrying `security_stamp` through on `route`.
+    pub fn allows(&self, security_stamp: &str, route: &str) -> bool {
+        !self.is_expired()
+            && self.security_stamp == security_stamp
+            && self.routes.as_ref().is_none_or(|routes| routes.iter().any(|r| r == route))
+    }
+}
+
 /// Local methods
 impl User {
     pub const CLIENT_KDF_TYPE_DEFAULT: i32 = UserKdfType::Pbkdf2 as i32;
@@ -159,9 +182,31 @@ impl User {
             external_id: None, // Todo: Needs to be removed in the future, this is not used anymore.
 
             key_id: None,
+
+            signed_public_key: None,
+            security_state: None,
+            security_version: None,
+            v2_upgrade_token: None,
         }
     }
 
+    pub fn is_v2(&self) -> bool {
+        self.signed_public_key.is_some() && self.security_state.is_some() && self.security_version.is_some()
+    }
+
+    /// Upstream's `HasV2Encryption`: a private key wrapped as `CoseEncrypt0B64` (type 7) and security version 2.
+    /// Upstream only uses it to decide which accounts need a v2-capable client.
+    ///
+    /// Ref: <https://github.com/bitwarden/server/blob/8da186ad73f80d37157fe6fd42323e4284e83ec1/src/Core/Entities/User.cs#L245-L278>
+    pub fn has_v2_encryption(&self) -> bool {
+        self.security_version == Some(2)
+            && self
+                .private_key
+                .as_deref()
+                .and_then(|private_key| private_key.split_once('.'))
+                .is_some_and(|(enc_type, _)| enc_type.parse::<u8>() == Ok(7))
+    }
+
     pub fn check_valid_password(&self, password: &str) -> bool {
         crypto::verify_password_hash(
             password.as_bytes(),
@@ -171,6 +216,7 @@ impl User {
         )
     }
 
+    /// Upstream's `GetMasterPasswordSalt`: there is no separate salt, so the normalized email
     pub fn master_password_salt(&self) -> String {
         self.email.trim().to_lowercase()
     }
@@ -225,10 +271,33 @@ impl User {
 
     pub async fn reset_security_stamp(&mut self, conn: &DbConn) -> EmptyResult {
         self.security_stamp = get_uuid();
+        // Keeps the unexpired route exceptions, set for the stamp being replaced, and drops a rotation's grace
+        let mut exceptions = self.stamp_exceptions();
+        exceptions.retain(|e| e.routes.is_some() && !e.is_expired());
+        self.set_stamp_exceptions(&exceptions);
         Device::rotate_refresh_tokens_by_user(&self.uuid, conn).await?;
         Ok(())
     }
 
+    /// Resets the stamp but lets issued access tokens run out, as upstream only checks it on refresh.
+    pub async fn reset_security_stamp_after_key_rotation(&mut self, conn: &DbConn) -> EmptyResult {
+        let previous_stamp = self.security_stamp.clone();
+        let mut grace: Vec<UserStampException> =
+            self.stamp_exceptions().into_iter().filter(|e| e.routes.is_none() && !e.is_expired()).collect();
+
+        self.reset_security_stamp(conn).await?;
+
+        grace.push(UserStampException {
+            routes: None,
+            security_stamp: previous_stamp,
+            expire: (Utc::now() + *DEFAULT_ACCESS_VALIDITY).timestamp(),
+        });
+        let mut exceptions = self.stamp_exceptions();
+        exceptions.extend(grace);
+        self.set_stamp_exceptions(&exceptions);
+        Ok(())
+    }
+
     /// Set the stamp_exception to only allow a subsequent request matching a specific route using the current security-stamp.
     ///
     /// # Arguments
@@ -237,17 +306,30 @@ impl User {
     ///   After these 2 minutes this stamp will expire.
     ///
     pub fn set_stamp_exception(&mut self, route_exception: Vec<String>) {
-        let stamp_exception = UserStampException {
+        self.set_stamp_exceptions(&[UserStampException {
-            routes: route_exception,
+            routes: Some(route_exception),
             security_stamp: self.security_stamp.clone(),
             expire: (Utc::now() + TimeDelta::try_minutes(2).unwrap()).timestamp(),
-        };
+        }]);
-        self.stamp_exception = Some(serde_json::to_string(&stamp_exception).unwrap_or_default());
     }
 
-    /// Resets the stamp_exception to prevent re-use of the previous security-stamp
+    /// The previous security stamps that are still accepted, expired ones included.
-    pub fn reset_stamp_exception(&mut self) {
+    pub fn stamp_exceptions(&self) -> Vec<UserStampException> {
-        self.stamp_exception = None;
+        let Some(stored) = self.stamp_exception.as_deref() else {
+            return Vec::new();
+        };
+        // Before key rotations kept sessions alive, only a single route exception was stored.
+        serde_json::from_str::<Vec<UserStampException>>(stored)
+            .or_else(|_| serde_json::from_str::<UserStampException>(stored).map(|e| vec![e]))
+            .unwrap_or_default()
+    }
+
+    fn set_stamp_exceptions(&mut self, exceptions: &[UserStampException]) {
+        self.stamp_exception = if exceptions.is_empty() {
+            None
+        } else {
+            Some(serde_json::to_string(&exceptions).unwrap_or_default())
+        };
     }
 
     pub fn display_name(&self) -> &str {
@@ -266,18 +348,37 @@ impl User {
         !CONFIG.mail_enabled() || self.verified_at.is_some()
     }
 
+    async fn v2_signature_key_pair(&self, conn: &DbConn) -> Option<UserSignatureKeyPair> {
+        if !self.is_v2() {
+            return None;
+        }
+        UserSignatureKeyPair::find_by_user(&self.uuid, conn).await
+    }
+
     /// The `accountKeys` object (upstream's `PrivateKeysResponseModel`), null without a key pair
-    pub fn account_keys_json(&self) -> Value {
+    pub async fn account_keys_json(&self, conn: &DbConn) -> Value {
         if self.private_key.is_some() {
+            let (signed_public_key, signature_key_pair, security_state) = match self.v2_signature_key_pair(conn).await {
+                Some(key_pair) => (
+                    json!(self.signed_public_key),
+                    key_pair.to_json(),
+                    json!({
+                        "securityState": self.security_state,
+                        "securityVersion": self.security_version,
+                    }),
+                ),
+                None => (Value::Null, Value::Null, Value::Null),
+            };
+
             json!({
                 "publicKeyEncryptionKeyPair": {
                     "wrappedPrivateKey": self.private_key,
                     "publicKey": self.public_key,
-                    "signedPublicKey": null,
+                    "signedPublicKey": signed_public_key,
                     "object": "publicKeyEncryptionKeyPair",
                 },
-                "securityState": null,
+                "securityState": security_state,
-                "signatureKeyPair": null,
+                "signatureKeyPair": signature_key_pair,
                 "object": "privateKeys"
             })
         } else {
@@ -285,6 +386,24 @@ impl User {
         }
     }
 
+    pub async fn public_keys_json(&self, conn: &DbConn) -> Value {
+        let (signed_public_key, verifying_key) = match self.v2_signature_key_pair(conn).await {
+            Some(key_pair) => (json!(self.signed_public_key), json!(key_pair.verifying_key)),
+            None => (Value::Null, Value::Null),
+        };
+
+        json!({
+            "publicKey": self.public_key,
+            "signedPublicKey": signed_public_key,
+            "verifyingKey": verifying_key,
+            "object": "publicKeys"
+        })
+    }
+
+    pub fn v2_upgrade_token_json(&self) -> Option<Value> {
+        self.v2_upgrade_token.as_ref().and_then(|token| serde_json::from_str(token).ok())
+    }
+
     pub async fn to_json(&self, conn: &DbConn) -> Value {
         let mut orgs_json = Vec::new();
         for c in Membership::find_confirmed_by_user(&self.uuid, conn).await {
@@ -305,7 +424,7 @@ impl User {
             UserStatus::Enabled
         };
 
-        let account_keys = self.account_keys_json();
+        let account_keys = self.account_keys_json(conn).await;
 
         json!({
             "_status": status as i32,
@@ -382,6 +501,7 @@ impl User {
         Device::delete_all_by_user(&self.uuid, conn).await?;
         TwoFactor::delete_all_by_user(&self.uuid, conn).await?;
         TwoFactorIncomplete::delete_all_by_user(&self.uuid, conn).await?;
+        UserSignatureKeyPair::delete_all_by_user(&self.uuid, conn).await?;
         Invitation::take(&self.email, conn).await; // Delete invitation if any
 
         conn.run(move |conn| {
@@ -553,25 +673,26 @@ impl Invitation {
 pub struct UserId(String);
 
 #[derive(
-    Clone,
+    Clone, Debug, DieselNewType, FromForm, PartialEq, Eq, Hash, Serialize, AsRef, Deref, Display, From, UuidFromParam,
-    Debug,
-    DieselNewType,
-    FromForm,
-    PartialEq,
-    Eq,
-    Hash,
-    Serialize,
-    Deserialize,
-    AsRef,
-    Deref,
-    Display,
-    From,
-    UuidFromParam,
 )]
 #[deref(forward)]
 #[from(forward)]
 pub struct KeyId(String);
 
+/// Like upstream, a key id is 32 lowercase hex characters. Key ids are compared as strings, so one in any other
+/// format would never match the id the clients send.
+///
+/// Ref: <https://github.com/bitwarden/server/blob/8da186ad73f80d37157fe6fd42323e4284e83ec1/src/Core/KeyManagement/Models/Data/KeyId.cs#L20-L42>
+impl<'de> serde::Deserialize<'de> for KeyId {
+    fn deserialize<D: serde::Deserializer<'de>>(deserializer: D) -> Result<Self, D::Error> {
+        let key_id = String::deserialize(deserializer)?;
+        if key_id.len() != 32 || !key_id.bytes().all(|b| matches!(b, b'0'..=b'9' | b'a'..=b'f')) {
+            return Err(serde::de::Error::custom("Key id must be 32 lowercase hex characters"));
+        }
+        Ok(Self(key_id))
+    }
+}
+
 impl SsoUser {
     pub async fn save(&self, conn: &DbConn) -> EmptyResult {
         db_run! { conn:
@@ -625,3 +746,39 @@ impl SsoUser {
         .await
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_key_id_format() {
+        let key_id: KeyId = serde_json::from_str(r#""0123456789abcdef0123456789abcdef""#).unwrap();
+        assert_eq!(key_id.as_ref(), "0123456789abcdef0123456789abcdef");
+
+        for invalid in ["", "0123456789ABCDEF0123456789ABCDEF", "0123456789abcdef", "0123456789abcdef0123456789abcdeg"]
+        {
+            assert!(serde_json::from_str::<KeyId>(&format!("\"{invalid}\"")).is_err(), "{invalid:?}");
+        }
+
+        // An absent key id stays optional
+        assert_eq!(serde_json::from_str::<Option<KeyId>>("null").unwrap(), None);
+    }
+
+    #[test]
+    fn test_has_v2_encryption() {
+        let user = |private_key: Option<&str>, security_version: Option<i32>| {
+            let mut user = User::new("user@example.com", None);
+            user.private_key = private_key.map(String::from);
+            user.security_version = security_version;
+            user
+        };
+
+        assert!(user(Some("7.cose"), Some(2)).has_v2_encryption());
+        assert!(!user(Some("7.cose"), Some(1)).has_v2_encryption());
+        assert!(!user(Some("7.cose"), None).has_v2_encryption());
+        assert!(!user(Some("2.iv|data|mac"), Some(2)).has_v2_encryption());
+        assert!(!user(Some("7"), Some(2)).has_v2_encryption());
+        assert!(!user(None, Some(2)).has_v2_encryption());
+    }
+}

src/db/models/user_signature_key_pair.rs

@@ -0,0 +1,132 @@
+use chrono::{NaiveDateTime, Utc};
+use derive_more::{AsRef, Deref, Display, From};
+use diesel::prelude::*;
+use serde_json::Value;
+
+use crate::{
+    api::EmptyResult,
+    db::{DbConn, schema::user_signature_key_pairs},
+    error::MapResult,
+    util::get_uuid,
+};
+
+use super::UserId;
+
+/// A user's signature key pair, part of the v2 state, in its own table like upstream.
+///
+/// Ref: <https://github.com/bitwarden/server/blob/9030c42bf7d8f9ac2ff9fee85c39588d5eb81499/src/Sql/dbo/KeyManagement/Tables/UserSignatureKeyPair.sql#L1-L15>
+#[derive(Identifiable, Queryable, Insertable, AsChangeset, Selectable)]
+#[diesel(table_name = user_signature_key_pairs)]
+#[diesel(treat_none_as_null = true)]
+#[diesel(primary_key(uuid))]
+pub struct UserSignatureKeyPair {
+    pub uuid: UserSignatureKeyPairId,
+    pub user_uuid: UserId,
+
+    pub signature_algorithm: i32,
+    /// The signing (private) key, wrapped by the user key.
+    pub signing_key: String,
+    /// The COSE-encoded public verifying key.
+    pub verifying_key: String,
+
+    pub created_at: NaiveDateTime,
+    pub updated_at: NaiveDateTime,
+}
+
+/// Ref: <https://github.com/bitwarden/server/blob/9030c42bf7d8f9ac2ff9fee85c39588d5eb81499/src/Core/KeyManagement/Enums/SignatureAlgorithm.cs#L6-L10>
+#[derive(Clone, Copy, Debug, PartialEq, Eq)]
+pub enum SignatureAlgorithm {
+    Ed25519 = 0,
+    MlDsa44 = 1,
+}
+
+impl SignatureAlgorithm {
+    pub fn parse(algorithm: &str) -> Option<Self> {
+        match algorithm {
+            "ed25519" => Some(Self::Ed25519),
+            "mldsa44" => Some(Self::MlDsa44),
+            _ => None,
+        }
+    }
+}
+
+/// Local methods
+impl UserSignatureKeyPair {
+    pub fn new(
+        user_uuid: UserId,
+        signature_algorithm: SignatureAlgorithm,
+        signing_key: String,
+        verifying_key: String,
+    ) -> Self {
+        let now = Utc::now().naive_utc();
+
+        Self {
+            uuid: UserSignatureKeyPairId(get_uuid()),
+            user_uuid,
+            signature_algorithm: signature_algorithm as i32,
+            signing_key,
+            verifying_key,
+            created_at: now,
+            updated_at: now,
+        }
+    }
+
+    pub fn to_json(&self) -> Value {
+        json!({
+            "wrappedSigningKey": self.signing_key,
+            "verifyingKey": self.verifying_key,
+            "object": "signatureKeyPair",
+        })
+    }
+}
+
+/// Database methods
+impl UserSignatureKeyPair {
+    pub async fn save(&mut self, conn: &DbConn) -> EmptyResult {
+        self.updated_at = Utc::now().naive_utc();
+
+        db_run! { conn:
+            mysql {
+                diesel::insert_into(user_signature_key_pairs::table)
+                    .values(&*self)
+                    .on_conflict(diesel::dsl::DuplicatedKeys)
+                    .do_update()
+                    .set(&*self)
+                    .execute(conn)
+                    .map_res("Error saving user signature key pair")
+            }
+            postgresql, sqlite {
+                diesel::insert_into(user_signature_key_pairs::table)
+                    .values(&*self)
+                    .on_conflict(user_signature_key_pairs::user_uuid)
+                    .do_update()
+                    .set(&*self)
+                    .execute(conn)
+                    .map_res("Error saving user signature key pair")
+            }
+        }
+    }
+
+    /// The user's key pair. There is at most one, enforced by a unique index on `user_uuid`.
+    pub async fn find_by_user(user_uuid: &UserId, conn: &DbConn) -> Option<Self> {
+        conn.run(move |conn| {
+            user_signature_key_pairs::table
+                .filter(user_signature_key_pairs::user_uuid.eq(user_uuid))
+                .first::<Self>(conn)
+                .ok()
+        })
+        .await
+    }
+
+    pub async fn delete_all_by_user(user_uuid: &UserId, conn: &DbConn) -> EmptyResult {
+        conn.run(move |conn| {
+            diesel::delete(user_signature_key_pairs::table.filter(user_signature_key_pairs::user_uuid.eq(user_uuid)))
+                .execute(conn)
+                .map_res("Error deleting user signature key pairs")
+        })
+        .await
+    }
+}
+
+#[derive(Clone, Debug, AsRef, Deref, DieselNewType, Display, From, Hash, PartialEq, Eq, Serialize, Deserialize)]
+pub struct UserSignatureKeyPairId(String);

src/db/schema.rs

@@ -219,6 +219,22 @@ table! {
         avatar_color -> Nullable<Text>,
         external_id -> Nullable<Text>,
         key_id -> Nullable<Text>,
+        signed_public_key -> Nullable<Text>,
+        security_state -> Nullable<Text>,
+        security_version -> Nullable<Integer>,
+        v2_upgrade_token -> Nullable<Text>,
+    }
+}
+
+table! {
+    user_signature_key_pairs (uuid) {
+        uuid -> Text,
+        user_uuid -> Text,
+        signature_algorithm -> Integer,
+        signing_key -> Text,
+        verifying_key -> Text,
+        created_at -> Timestamp,
+        updated_at -> Timestamp,
     }
 }
 
@@ -244,6 +260,7 @@ table! {
         atype -> Integer,
         reset_password_key -> Nullable<Text>,
         external_id -> Nullable<Text>,
+        v2_upgrade_token -> Nullable<Text>,
     }
 }
 
@@ -384,6 +401,7 @@ joinable!(collections_groups -> groups (groups_uuid));
 joinable!(event -> users_organizations (uuid));
 joinable!(auth_requests -> users (user_uuid));
 joinable!(sso_users -> users (user_uuid));
+joinable!(user_signature_key_pairs -> users (user_uuid));
 
 allow_tables_to_appear_in_same_query!(
     archives,
@@ -410,4 +428,5 @@ allow_tables_to_appear_in_same_query!(
     collections_groups,
     event,
     auth_requests,
+    user_signature_key_pairs,
 );

src/util.rs

@@ -884,6 +884,12 @@ pub fn parse_experimental_client_feature_flags(
         .collect()
 }
 
+/// Whether the admin enabled this supported client feature flag
+pub fn is_client_feature_flag_enabled(flag: &str) -> bool {
+    parse_experimental_client_feature_flags(&CONFIG.experimental_client_feature_flags(), &FeatureFlagFilter::ValidOnly)
+        .contains_key(flag)
+}
+
 /// TODO: This is extracted from IpAddr::is_global, which is unstable:
 /// https://doc.rust-lang.org/nightly/std/net/enum.IpAddr.html#method.is_global
 /// Remove once https://github.com/rust-lang/rust/issues/27709 is merged

tools/sdk-live-tests/register_vector.py

@@ -0,0 +1,129 @@
+#!/usr/bin/env python3
+"""Registers the account of an sdk-internal test vector on a vaultwarden server, as a client would.
+
+Usage: register_vector.py <vector.json> <server-url>
+
+A V1 vector is registered with the flat `keys` object, a V2 one with `accountKeys` and the user key
+id. Prints the account's email and password on two lines, for the caller to log in with.
+
+Exits with SKIP, and the reason on stderr, for a vector the live tests can't use.
+"""
+
+import json
+import sys
+import urllib.error
+import urllib.request
+
+SKIP = 3
+MIN_PBKDF2_ITERATIONS = 100_000
+
+
+def skip_reason(vector):
+    if not any("masterPasswordUnlock" in m for m in vector["unlockMethods"]):
+        return "it has no master password, which the live tests log in with"
+    pbkdf2 = vector["account"]["kdf"].get("pBKDF2")
+    if pbkdf2 is not None and pbkdf2["iterations"] < MIN_PBKDF2_ITERATIONS:
+        return f"registration requires at least {MIN_PBKDF2_ITERATIONS} PBKDF2 iterations (upstream 600000)"
+    return None
+
+
+def kdf_of(account):
+    kind, params = next(iter(account["kdf"].items()))
+    if kind == "pBKDF2":
+        return {"kdfType": 0, "iterations": params["iterations"]}
+    return {
+        "kdfType": 1,
+        "iterations": params["iterations"],
+        "memory": params["memory"],
+        "parallelism": params["parallelism"],
+    }
+
+
+def register_body(vector):
+    account = vector["account"]
+    raw = vector["rawCryptographicState"]
+    version, state = next(iter(account["accountCryptographicState"].items()))
+    kdf = kdf_of(account)
+    unlock = next(m["masterPasswordUnlock"] for m in vector["unlockMethods"] if "masterPasswordUnlock" in m)
+    mp_unlock = unlock["master_password_unlock"]
+
+    body = {
+        "email": account["email"],
+        "masterPasswordHint": None,
+        "masterPasswordAuthentication": {
+            "kdf": kdf,
+            "salt": mp_unlock["salt"],
+            "masterPasswordAuthenticationHash": vector["masterPasswordAuthenticationHash"],
+        },
+        "masterPasswordUnlock": {
+            "kdf": kdf,
+            "salt": mp_unlock["salt"],
+            "masterKeyWrappedUserKey": mp_unlock["masterKeyWrappedUserKey"],
+        },
+    }
+
+    if version == "V2":
+        body["masterPasswordUnlock"]["containedKeyId"] = raw["userKeyId"]
+        body["accountKeys"] = {
+            "userKeyEncryptedAccountPrivateKey": state["private_key"],
+            "accountPublicKey": raw["publicKey"],
+            "publicKeyEncryptionKeyPair": {
+                "wrappedPrivateKey": state["private_key"],
+                "publicKey": raw["publicKey"],
+                "signedPublicKey": state["signed_public_key"],
+            },
+            "signatureKeyPair": {
+                "signatureAlgorithm": "ed25519",
+                "wrappedSigningKey": state["signing_key"],
+                "verifyingKey": raw["verifyingKey"],
+            },
+            "securityState": {
+                "securityState": state["security_state"],
+                "securityVersion": account["securityVersion"],
+            },
+        }
+    else:
+        body["keys"] = {"encryptedPrivateKey": state["private_key"], "publicKey": raw["publicKey"]}
+
+    return body, unlock["password"]
+
+
+def post(url, body):
+    request = urllib.request.Request(
+        url,
+        data=json.dumps(body).encode(),
+        headers={"Content-Type": "application/json", "Accept": "application/json"},
+        method="POST",
+    )
+    try:
+        with urllib.request.urlopen(request) as response:
+            return response.read()
+    except urllib.error.HTTPError as e:
+        sys.exit(f"Registering {body['email']} failed at {url}: {e.code} {e.read().decode()}")
+
+
+def main():
+    with open(sys.argv[1]) as f:
+        vector = json.load(f)
+    server = sys.argv[2].rstrip("/")
+
+    reason = skip_reason(vector)
+    if reason is not None:
+        print(f"Skipped: {reason}", file=sys.stderr)
+        sys.exit(SKIP)
+
+    body, password = register_body(vector)
+    # With signup verification off, the server returns the token instead of mailing it
+    token = post(
+        f"{server}/identity/accounts/register/send-verification-email",
+        {"email": body["email"], "name": vector["name"]},
+    )
+    body["emailVerificationToken"] = json.loads(token)
+    post(f"{server}/identity/accounts/register/finish", body)
+
+    print(body["email"])
+    print(password)
+
+
+if __name__ == "__main__":
+    main()

tools/sdk-live-tests/run.sh

@@ -0,0 +1,61 @@
+#!/usr/bin/env bash
+# Runs the live-server integration tests of bitwarden/sdk-internal against vaultwarden.
+#
+# Usage: tools/sdk-live-tests/run.sh --sdk-dir <path> [--skip-sdk-build]
+#
+# Every test vector of the SDK (test-vectors/users/) that the tests can log in with gets a fresh
+# server and database, since the tests rotate the account's keys. Stops at the first failure; the
+# server logs are in target/sdk-live-tests/. Building the SDK needs its Rust toolchain with the
+# wasm32-unknown-unknown target and rust-src, Node.js, and binaryen (`npm i -g binaryen@132.0.0`).
+set -euo pipefail
+
+VW_DIR="$(cd "$(dirname "$0")/../.." && pwd)"
+OUT_DIR="${VW_DIR}/target/sdk-live-tests"
+URL="http://127.0.0.1:8099"
+SKIP=3 # register_vector.py's exit code for a vector the tests can't use
+
+SDK_DIR=""
+BUILD_SDK=1
+while [[ $# -gt 0 ]]; do
+  case "$1" in
+    --sdk-dir) SDK_DIR="$(cd "$2" && pwd)"; shift 2 ;;
+    --skip-sdk-build) BUILD_SDK=0; shift ;;
+    *) echo "Unknown argument: $1" >&2; exit 2 ;;
+  esac
+done
+[[ -n "${SDK_DIR}" ]] || { echo "--sdk-dir is required" >&2; exit 2; }
+TESTS_DIR="${SDK_DIR}/crates/bitwarden-wasm-internal/integration-tests"
+
+(cd "${VW_DIR}" && cargo build --features sqlite)
+if [[ ${BUILD_SDK} -eq 1 ]]; then
+  bash "${SDK_DIR}/crates/bitwarden-wasm-internal/build.sh"
+  (cd "${TESTS_DIR}" && npm ci)
+fi
+
+trap 'kill $(jobs -p) 2>/dev/null || true' EXIT
+
+for vector_file in "${SDK_DIR}"/test-vectors/users/*.json; do
+  vector="$(basename "${vector_file}" .json)"
+  echo "=== ${vector}"
+  data_dir="${OUT_DIR}/${vector}"
+  rm -rf "${data_dir}" && mkdir -p "${data_dir}"
+
+  DATA_FOLDER="${data_dir}" DATABASE_URL="sqlite://${data_dir}/db.sqlite3" \
+    ROCKET_ADDRESS=127.0.0.1 ROCKET_PORT=8099 DOMAIN="${URL}" WEB_VAULT_ENABLED=false \
+    SIGNUPS_ALLOWED=true SIGNUPS_VERIFY=false LOGIN_RATELIMIT_MAX_BURST=1000 \
+    "${VW_DIR}/target/debug/vaultwarden" > "${data_dir}/vaultwarden.log" 2>&1 &
+  server=$!
+  curl -sf --retry 30 --retry-connrefused --retry-delay 1 "${URL}/alive" > /dev/null
+
+  status=0
+  credentials="$(python3 "${VW_DIR}/tools/sdk-live-tests/register_vector.py" "${vector_file}" "${URL}")" || status=$?
+  if [[ ${status} -eq 0 ]]; then
+    (cd "${TESTS_DIR}" && BW_LIVE_SERVER_URL="${URL}" BW_LIVE_EMAIL="$(sed -n 1p <<< "${credentials}")" \
+      BW_LIVE_PASSWORD="$(sed -n 2p <<< "${credentials}")" npm run test:live)
+  elif [[ ${status} -ne ${SKIP} ]]; then
+    exit "${status}"
+  fi
+
+  kill "${server}" && wait "${server}" || true
+done
+echo "All test vectors passed"