diff --git a/.github/workflows/e2e-test.yml b/.github/workflows/e2e-test.yml
index c123790580..88c15b873c 100644
--- a/.github/workflows/e2e-test.yml
+++ b/.github/workflows/e2e-test.yml
@@ -59,6 +59,9 @@ jobs:
           - suite: rust-docker
             cmd: "mise run --no-deps --skip-deps e2e:rust"
             apt_packages: "openssh-client"
+          - suite: supervisor-middleware
+            cmd: "mise run --no-deps --skip-deps e2e:supervisor-middleware"
+            apt_packages: "openssh-client"
           - suite: mcp
             cmd: "mise run --no-deps --skip-deps e2e:mcp"
             apt_packages: ""
diff --git a/Cargo.lock b/Cargo.lock
index d676de7782..3ca7fc0ee3 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -4066,6 +4066,7 @@ dependencies = [
  "futures",
  "hyper 1.9.0",
  "hyper-util",
+ "jsonwebtoken",
  "miette",
  "oauth2",
  "openshell-core",
diff --git a/crates/openshell-sdk/Cargo.toml b/crates/openshell-sdk/Cargo.toml
index 8d80beaa74..2f03d03794 100644
--- a/crates/openshell-sdk/Cargo.toml
+++ b/crates/openshell-sdk/Cargo.toml
@@ -10,17 +10,26 @@ rust-version.workspace = true
 license.workspace = true
 repository.workspace = true
 
+[features]
+default = []
+extension = [
+    "dep:jsonwebtoken",
+    "dep:serde_json",
+]
+
 [dependencies]
 openshell-core = { path = "../openshell-core" }
 async-trait = "0.1"
 futures = { workspace = true }
 hyper = { workspace = true }
 hyper-util = { workspace = true }
+jsonwebtoken = { workspace = true, optional = true }
 miette = { workspace = true }
 oauth2 = { version = "5", default-features = false, features = ["reqwest"] }
 reqwest = { workspace = true }
 rustls = { workspace = true }
 serde = { workspace = true }
+serde_json = { workspace = true, optional = true }
 thiserror = { workspace = true }
 tokio = { workspace = true }
 tokio-rustls = { workspace = true }
diff --git a/crates/openshell-sdk/README.md b/crates/openshell-sdk/README.md
index 93afc5359e..b5f6f1b502 100644
--- a/crates/openshell-sdk/README.md
+++ b/crates/openshell-sdk/README.md
@@ -49,6 +49,17 @@ mTLS (client certificates) is not supported.
 SDK-shaped enums rather than raw proto integers. Failures map to a typed
 `SdkError` with a discriminable kind.
 
+Enable the `extension` Cargo feature when building an OpenShell extension
+service:
+
+```toml
+openshell-sdk = { version = "...", features = ["extension"] }
+```
+
+The `extension` module provides common SDK building blocks for extension
+services. It currently handles caller verification; shared service interfaces
+and observability support will follow.
+
 ## Modules
 
 | Module | Purpose |
@@ -60,6 +71,7 @@ SDK-shaped enums rather than raw proto integers. Failures map to a typed
 | `oidc` | OIDC token handling at the transport layer. |
 | `refresh` | `Refresh` trait and single-flight refresh coalescing. |
 | `edge_tunnel` | Cloudflare Access tunnel dialer. |
+| `extension` | Opt-in SDK building blocks for extension services. |
 | `error` | `SdkError` taxonomy. |
 | `types` | Curated request/response types and proto conversions. |
 | `raw` | Escape hatch re-exporting the generated tonic clients. |
diff --git a/crates/openshell-sdk/src/extension/auth.rs b/crates/openshell-sdk/src/extension/auth.rs
new file mode 100644
index 0000000000..6d7d8ebb71
--- /dev/null
+++ b/crates/openshell-sdk/src/extension/auth.rs
@@ -0,0 +1,409 @@
+// SPDX-FileCopyrightText: Copyright (c) 2025-2026 NVIDIA CORPORATION & AFFILIATES. All rights reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+use std::collections::HashMap;
+use std::time::Duration;
+
+use jsonwebtoken::{
+    Algorithm, DecodingKey, Validation, decode, decode_header,
+    jwk::{AlgorithmParameters, EllipticCurve, JwkSet, PublicKeyUse},
+};
+use serde::{Deserialize, Serialize};
+use tonic::{Request, Status};
+
+const CLOCK_SKEW_SECS: i64 = 30;
+const EXTENSION_JWT_TYP: &str = "openshell-ext+jwt";
+const MAX_EXTENSION_TOKEN_TTL: Duration = Duration::from_secs(3_600);
+
+/// `OpenShell` component authenticated as the caller of an extension service.
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Hash, Serialize, Deserialize)]
+#[serde(rename_all = "snake_case")]
+pub enum ExtensionCallerKind {
+    Gateway,
+    Supervisor,
+}
+
+/// Private wire representation of gateway-minted extension claims.
+///
+/// Keeping the claims internal lets the SDK expose a stable, normalized caller
+/// identity without making the gateway's token schema part of its public API.
+#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
+struct ExtensionJwtClaims {
+    iss: String,
+    aud: String,
+    sub: String,
+    iat: i64,
+    exp: i64,
+    jti: String,
+    caller_kind: ExtensionCallerKind,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    sandbox_id: Option<String>,
+}
+
+/// Verified identity presented by an `OpenShell` component to an extension.
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub struct AuthenticatedCaller {
+    pub kind: ExtensionCallerKind,
+    pub subject: String,
+    pub sandbox_id: Option<String>,
+}
+
+/// Verifies gateway-minted JWTs presented to an extension service.
+///
+/// The public key or JWKS document must come from a trusted operator channel.
+/// Parsing key material does not establish trust in it.
+pub struct GatewayJwtAuthenticator {
+    keys: HashMap<String, DecodingKey>,
+    issuer: String,
+    audience: String,
+}
+
+impl std::fmt::Debug for GatewayJwtAuthenticator {
+    fn fmt(&self, formatter: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        formatter
+            .debug_struct("GatewayJwtAuthenticator")
+            .field("key_ids", &self.keys.keys())
+            .field("issuer", &self.issuer)
+            .field("audience", &self.audience)
+            .finish()
+    }
+}
+
+impl GatewayJwtAuthenticator {
+    /// Construct a verifier from one trusted Ed25519 public key.
+    pub fn from_ed25519_pem(
+        public_key_pem: &[u8],
+        key_id: impl Into<String>,
+        issuer: impl Into<String>,
+        audience: impl Into<String>,
+    ) -> Result<Self, VerificationError> {
+        let key_id = key_id.into();
+        if key_id.is_empty() {
+            return Err(VerificationError::MissingKeyId);
+        }
+        let key = DecodingKey::from_ed_pem(public_key_pem)
+            .map_err(VerificationError::InvalidPublicKey)?;
+        Self::new(HashMap::from([(key_id, key)]), issuer, audience)
+    }
+
+    /// Construct a verifier from a trusted JWKS document.
+    pub fn from_jwks(
+        jwks_json: &[u8],
+        issuer: impl Into<String>,
+        audience: impl Into<String>,
+    ) -> Result<Self, VerificationError> {
+        let jwks: JwkSet = serde_json::from_slice(jwks_json)?;
+        let mut keys = HashMap::with_capacity(jwks.keys.len());
+
+        for jwk in jwks.keys {
+            let key_id = jwk
+                .common
+                .key_id
+                .clone()
+                .filter(|key_id| !key_id.is_empty())
+                .ok_or(VerificationError::MissingKeyId)?;
+            let supported = jwk.common.key_algorithm
+                == Some(jsonwebtoken::jwk::KeyAlgorithm::EdDSA)
+                && jwk.common.public_key_use == Some(PublicKeyUse::Signature)
+                && matches!(
+                    &jwk.algorithm,
+                    AlgorithmParameters::OctetKeyPair(parameters)
+                        if parameters.curve == EllipticCurve::Ed25519
+                );
+            if !supported {
+                return Err(VerificationError::UnsupportedKey(key_id));
+            }
+            let key = DecodingKey::from_jwk(&jwk)
+                .map_err(|_| VerificationError::UnsupportedKey(key_id.clone()))?;
+            if keys.insert(key_id.clone(), key).is_some() {
+                return Err(VerificationError::DuplicateKeyId(key_id));
+            }
+        }
+
+        Self::new(keys, issuer, audience)
+    }
+
+    fn new(
+        keys: HashMap<String, DecodingKey>,
+        issuer: impl Into<String>,
+        audience: impl Into<String>,
+    ) -> Result<Self, VerificationError> {
+        if keys.is_empty() {
+            return Err(VerificationError::EmptyKeySet);
+        }
+        let issuer = issuer.into();
+        let audience = audience.into();
+        if issuer.is_empty() || audience.is_empty() {
+            return Err(VerificationError::EmptyExpectedIdentity);
+        }
+        Ok(Self {
+            keys,
+            issuer,
+            audience,
+        })
+    }
+
+    /// Verify a bearer token and return its normalized caller identity.
+    pub fn authenticate(
+        &self,
+        bearer_token: &str,
+    ) -> Result<AuthenticatedCaller, VerificationError> {
+        let header = decode_header(bearer_token).map_err(VerificationError::InvalidToken)?;
+        if header.typ.as_deref() != Some(EXTENSION_JWT_TYP) {
+            return Err(VerificationError::UnexpectedTokenType);
+        }
+        if header.alg != Algorithm::EdDSA {
+            return Err(VerificationError::UnexpectedAlgorithm);
+        }
+        let key_id = header
+            .kid
+            .as_deref()
+            .filter(|key_id| !key_id.is_empty())
+            .ok_or(VerificationError::MissingTokenKeyId)?;
+        let key = self
+            .keys
+            .get(key_id)
+            .ok_or_else(|| VerificationError::UnknownKeyId(key_id.to_string()))?;
+
+        let mut validation = Validation::new(Algorithm::EdDSA);
+        validation.algorithms = vec![Algorithm::EdDSA];
+        validation.leeway = u64::try_from(CLOCK_SKEW_SECS).unwrap_or_default();
+        validation.set_issuer(&[&self.issuer]);
+        validation.set_audience(&[&self.audience]);
+        validation.set_required_spec_claims(&[
+            "iss",
+            "aud",
+            "sub",
+            "iat",
+            "exp",
+            "jti",
+            "caller_kind",
+        ]);
+
+        let claims = decode::<ExtensionJwtClaims>(bearer_token, key, &validation)
+            .map_err(VerificationError::InvalidToken)?
+            .claims;
+        validate_claim_shape(&claims)?;
+        Ok(AuthenticatedCaller {
+            kind: claims.caller_kind,
+            subject: claims.sub,
+            sandbox_id: claims.sandbox_id,
+        })
+    }
+
+    /// Extract and verify the bearer credential on a tonic request.
+    ///
+    /// Detailed verification failures remain available through
+    /// [`Self::authenticate`]. This helper returns a stable gRPC error that
+    /// does not expose verifier internals to an untrusted caller.
+    pub fn authenticate_request<T>(
+        &self,
+        request: &Request<T>,
+    ) -> Result<AuthenticatedCaller, Status> {
+        let authorization = request
+            .metadata()
+            .get("authorization")
+            .ok_or_else(|| Status::unauthenticated("missing extension authorization"))?
+            .to_str()
+            .map_err(|_| Status::unauthenticated("invalid extension authorization"))?;
+        let token = authorization
+            .strip_prefix("Bearer ")
+            .filter(|token| !token.is_empty())
+            .ok_or_else(|| Status::unauthenticated("expected an extension bearer token"))?;
+        self.authenticate(token)
+            .map_err(|_| Status::unauthenticated("invalid extension token"))
+    }
+}
+
+fn validate_claim_shape(claims: &ExtensionJwtClaims) -> Result<(), VerificationError> {
+    if claims.jti.is_empty() {
+        return Err(VerificationError::InvalidClaims("jti must not be empty"));
+    }
+    if claims.exp <= claims.iat {
+        return Err(VerificationError::InvalidClaims(
+            "exp must be later than iat",
+        ));
+    }
+    let max_lifetime = i64::try_from(MAX_EXTENSION_TOKEN_TTL.as_secs()).unwrap_or(i64::MAX);
+    if claims.exp.saturating_sub(claims.iat) > max_lifetime {
+        return Err(VerificationError::InvalidClaims(
+            "token lifetime exceeds the extension maximum",
+        ));
+    }
+    let now = i64::try_from(jsonwebtoken::get_current_timestamp()).unwrap_or(i64::MAX);
+    if claims.iat > now.saturating_add(CLOCK_SKEW_SECS) {
+        return Err(VerificationError::InvalidClaims(
+            "iat is later than the allowed clock skew",
+        ));
+    }
+
+    match (claims.caller_kind, claims.sandbox_id.as_deref()) {
+        (ExtensionCallerKind::Gateway, None) if claims.sub == claims.iss => Ok(()),
+        (ExtensionCallerKind::Supervisor, Some(sandbox_id))
+            if !sandbox_id.is_empty()
+                && claims.sub == format!("spiffe://openshell/sandbox/{sandbox_id}") =>
+        {
+            Ok(())
+        }
+        (ExtensionCallerKind::Gateway, _) => Err(VerificationError::InvalidClaims(
+            "gateway caller identity is inconsistent",
+        )),
+        (ExtensionCallerKind::Supervisor, _) => Err(VerificationError::InvalidClaims(
+            "supervisor caller identity is inconsistent",
+        )),
+    }
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum VerificationError {
+    #[error("invalid JWKS document: {0}")]
+    InvalidJwks(#[from] serde_json::Error),
+    #[error("invalid Ed25519 public key: {0}")]
+    InvalidPublicKey(jsonwebtoken::errors::Error),
+    #[error("extension key is missing a key ID")]
+    MissingKeyId,
+    #[error("JWKS contains duplicate key ID '{0}'")]
+    DuplicateKeyId(String),
+    #[error("JWKS key '{0}' is not a supported Ed25519 signing key")]
+    UnsupportedKey(String),
+    #[error("extension key set is empty")]
+    EmptyKeySet,
+    #[error("expected issuer and audience must not be empty")]
+    EmptyExpectedIdentity,
+    #[error("token does not use the OpenShell extension JWT type")]
+    UnexpectedTokenType,
+    #[error("token does not use EdDSA")]
+    UnexpectedAlgorithm,
+    #[error("token header does not contain a key ID")]
+    MissingTokenKeyId,
+    #[error("token references unknown key ID '{0}'")]
+    UnknownKeyId(String),
+    #[error("token validation failed: {0}")]
+    InvalidToken(jsonwebtoken::errors::Error),
+    #[error("invalid extension claims: {0}")]
+    InvalidClaims(&'static str),
+}
+
+#[cfg(test)]
+mod tests {
+    use jsonwebtoken::{EncodingKey, Header, encode};
+
+    use super::*;
+
+    const PRIVATE_KEY: &[u8] = b"-----BEGIN PRIVATE KEY-----\nMC4CAQAwBQYDK2VwBCIEIGrD/e7uKYqSY4twDEsRfMMuLSrODf14dpTiTK6K1YI0\n-----END PRIVATE KEY-----\n";
+    const PUBLIC_KEY: &[u8] = b"-----BEGIN PUBLIC KEY-----\nMCowBQYDK2VwAyEA2+Jj2UvNCvQiUPNYRgSi0cJSPiJI6Rs6D0UTeEpQVj8=\n-----END PUBLIC KEY-----\n";
+    const JWKS: &[u8] = br#"{"keys":[{"kty":"OKP","use":"sig","crv":"Ed25519","x":"2-Jj2UvNCvQiUPNYRgSi0cJSPiJI6Rs6D0UTeEpQVj8","kid":"test-key","alg":"EdDSA"}]}"#;
+
+    fn claims(kind: ExtensionCallerKind) -> ExtensionJwtClaims {
+        let now = i64::try_from(jsonwebtoken::get_current_timestamp()).unwrap();
+        let (subject, sandbox_id) = match kind {
+            ExtensionCallerKind::Gateway => ("openshell-gateway:test".into(), None),
+            ExtensionCallerKind::Supervisor => (
+                "spiffe://openshell/sandbox/sandbox-1".into(),
+                Some("sandbox-1".into()),
+            ),
+        };
+        ExtensionJwtClaims {
+            iss: "openshell-gateway:test".into(),
+            aud: "urn:openshell:extension:middleware:test".into(),
+            sub: subject,
+            iat: now,
+            exp: now + 300,
+            jti: "unique".into(),
+            caller_kind: kind,
+            sandbox_id,
+        }
+    }
+
+    fn token(claims: &ExtensionJwtClaims, token_type: Option<&str>) -> String {
+        let mut header = Header::new(Algorithm::EdDSA);
+        header.kid = Some("test-key".into());
+        header.typ = token_type.map(str::to_string);
+        encode(
+            &header,
+            claims,
+            &EncodingKey::from_ed_pem(PRIVATE_KEY).unwrap(),
+        )
+        .unwrap()
+    }
+
+    fn verifier() -> GatewayJwtAuthenticator {
+        GatewayJwtAuthenticator::from_jwks(
+            JWKS,
+            "openshell-gateway:test",
+            "urn:openshell:extension:middleware:test",
+        )
+        .unwrap()
+    }
+
+    #[test]
+    fn authenticates_gateway_and_supervisor_callers() {
+        for kind in [
+            ExtensionCallerKind::Gateway,
+            ExtensionCallerKind::Supervisor,
+        ] {
+            let expected = claims(kind);
+            let caller = verifier()
+                .authenticate(&token(&expected, Some(EXTENSION_JWT_TYP)))
+                .unwrap();
+            assert_eq!(caller.kind, kind);
+            assert_eq!(caller.subject, expected.sub);
+            assert_eq!(caller.sandbox_id, expected.sandbox_id);
+        }
+    }
+
+    #[test]
+    fn pem_and_jwks_constructors_accept_the_same_key() {
+        let verifier = GatewayJwtAuthenticator::from_ed25519_pem(
+            PUBLIC_KEY,
+            "test-key",
+            "openshell-gateway:test",
+            "urn:openshell:extension:middleware:test",
+        )
+        .unwrap();
+        assert!(
+            verifier
+                .authenticate(&token(
+                    &claims(ExtensionCallerKind::Gateway),
+                    Some(EXTENSION_JWT_TYP)
+                ))
+                .is_ok()
+        );
+    }
+
+    #[test]
+    fn rejects_untyped_and_inconsistent_credentials() {
+        let verifier = verifier();
+        assert!(matches!(
+            verifier.authenticate(&token(&claims(ExtensionCallerKind::Gateway), None)),
+            Err(VerificationError::UnexpectedTokenType)
+        ));
+
+        let mut inconsistent = claims(ExtensionCallerKind::Supervisor);
+        inconsistent.sub = "spiffe://openshell/sandbox/someone-else".into();
+        assert!(matches!(
+            verifier.authenticate(&token(&inconsistent, Some(EXTENSION_JWT_TYP))),
+            Err(VerificationError::InvalidClaims(_))
+        ));
+    }
+
+    #[test]
+    fn request_helper_returns_stable_unauthenticated_errors() {
+        let verifier = verifier();
+        assert_eq!(
+            verifier
+                .authenticate_request(&Request::new(()))
+                .unwrap_err()
+                .code(),
+            tonic::Code::Unauthenticated
+        );
+
+        let mut request = Request::new(());
+        request
+            .metadata_mut()
+            .insert("authorization", "Bearer invalid".parse().unwrap());
+        let error = verifier.authenticate_request(&request).unwrap_err();
+        assert_eq!(error.code(), tonic::Code::Unauthenticated);
+        assert_eq!(error.message(), "invalid extension token");
+    }
+}
diff --git a/crates/openshell-sdk/src/extension/mod.rs b/crates/openshell-sdk/src/extension/mod.rs
new file mode 100644
index 0000000000..8a2d1b763a
--- /dev/null
+++ b/crates/openshell-sdk/src/extension/mod.rs
@@ -0,0 +1,13 @@
+// SPDX-FileCopyrightText: Copyright (c) 2025-2026 NVIDIA CORPORATION & AFFILIATES. All rights reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+//! APIs for building `OpenShell` extension services.
+//!
+//! This feature is the home for shared extension interfaces, verification, and
+//! observability. It currently provides gateway-minted credential verification.
+
+mod auth;
+
+pub use auth::{
+    AuthenticatedCaller, ExtensionCallerKind, GatewayJwtAuthenticator, VerificationError,
+};
diff --git a/crates/openshell-sdk/src/lib.rs b/crates/openshell-sdk/src/lib.rs
index dbf2524a2a..c57944ca1b 100644
--- a/crates/openshell-sdk/src/lib.rs
+++ b/crates/openshell-sdk/src/lib.rs
@@ -34,6 +34,8 @@ pub mod client;
 pub mod config;
 pub mod edge_tunnel;
 pub mod error;
+#[cfg(feature = "extension")]
+pub mod extension;
 pub mod oidc;
 pub mod raw;
 pub mod refresh;
diff --git a/docs/extensibility/supervisor-middleware.mdx b/docs/extensibility/supervisor-middleware.mdx
index 42beedeff9..877f818429 100644
--- a/docs/extensibility/supervisor-middleware.mdx
+++ b/docs/extensibility/supervisor-middleware.mdx
@@ -90,6 +90,8 @@ Return your expected audience in the `expected_audience` field of your `Describe
 
 Provision the trusted gateway URL, expected gateway ID, and public key or JWKS through the deployment. This operator-provisioned key material is the authoritative cold-start trust anchor. The expected issuer is exactly `openshell-gateway:<gateway_id>`; fetching JWKS does not establish that identity by itself. After initial trust is established, `GET /.well-known/openid-configuration` and its `jwks_uri` provide steady-state key refresh and operational convenience. The document is OIDC-shaped rather than OIDC-compliant: `issuer` is the gateway identity, not the URL serving the document, so compare `iss` against the configured value and fetch updates only over authenticated TLS at the trusted gateway URL.
 
+Rust services can enable the `extension` Cargo feature on `openshell-sdk` for common extension interfaces, verification, and observability. Caller verification is available today through `openshell_sdk::extension::GatewayJwtAuthenticator`; additional SDK support will follow.
+
 Cache keys by `kid`. Validate, at minimum:
 
 - `typ` is exactly `openshell-ext+jwt`. Extension tokens and sandbox-to-gateway bootstrap tokens share a signing key and differ only in audience; this header is a second, independent discriminator.
diff --git a/e2e/rust/Cargo.toml b/e2e/rust/Cargo.toml
index 9ff52c73ab..8b27c89b18 100644
--- a/e2e/rust/Cargo.toml
+++ b/e2e/rust/Cargo.toml
@@ -141,6 +141,11 @@ name = "proxy_egress_pipeline"
 path = "tests/proxy_egress_pipeline.rs"
 required-features = ["e2e-host-gateway"]
 
+[[test]]
+name = "supervisor_middleware"
+path = "tests/supervisor_middleware.rs"
+required-features = ["e2e-docker"]
+
 [[test]]
 name = "workspace_namespace_managed"
 path = "tests/workspace_namespace_managed.rs"
diff --git a/e2e/rust/tests/supervisor_middleware.rs b/e2e/rust/tests/supervisor_middleware.rs
new file mode 100644
index 0000000000..5bfdacb88f
--- /dev/null
+++ b/e2e/rust/tests/supervisor_middleware.rs
@@ -0,0 +1,123 @@
+// SPDX-FileCopyrightText: Copyright (c) 2025-2026 NVIDIA CORPORATION & AFFILIATES. All rights reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+//! Black-box happy-path coverage for authenticated supervisor middleware.
+
+#![cfg(feature = "e2e-docker")]
+
+use std::io::Write;
+
+use openshell_e2e::harness::container::ContainerHttpServer;
+use openshell_e2e::harness::sandbox::SandboxGuard;
+use serde_json::Value;
+use tempfile::NamedTempFile;
+
+async fn start_test_server() -> Result<ContainerHttpServer, String> {
+    let script = r#"from http.server import BaseHTTPRequestHandler, HTTPServer
+import json
+
+class Handler(BaseHTTPRequestHandler):
+    def do_GET(self):
+        self.send_response(200)
+        self.end_headers()
+
+    def do_POST(self):
+        body = self.rfile.read(int(self.headers.get("Content-Length", "0")))
+        parsed = json.loads(body)
+        response = json.dumps({
+            "received_payload": parsed.get("payload"),
+            "fixture_header": self.headers.get("x-openshell-middleware-fixture"),
+        }, sort_keys=True).encode()
+        self.send_response(200)
+        self.send_header("Content-Type", "application/json")
+        self.send_header("Content-Length", str(len(response)))
+        self.end_headers()
+        self.wfile.write(response)
+
+    def log_message(self, format, *args):
+        pass
+
+HTTPServer(("0.0.0.0", 8000), Handler).serve_forever()
+"#;
+    ContainerHttpServer::start_python("middleware-happy.openshell.test", script).await
+}
+
+fn write_policy(host: &str, port: u16) -> Result<NamedTempFile, String> {
+    let mut file = NamedTempFile::new().map_err(|error| format!("create policy: {error}"))?;
+    let policy = format!(
+        r#"version: 1
+
+network_middlewares:
+  scripted-e2e:
+    name: Scripted E2E middleware
+    middleware: e2e-scripted
+    order: 10
+    config: {{}}
+    on_error: fail_closed
+    endpoints:
+      include:
+        - {host}
+
+network_policies:
+  middleware_target:
+    name: middleware_target
+    endpoints:
+      - host: {host}
+        port: {port}
+        protocol: rest
+        enforcement: enforce
+        allowed_ips:
+          - "10.0.0.0/8"
+          - "172.0.0.0/8"
+          - "192.168.0.0/16"
+          - "fc00::/7"
+        rules:
+          - allow:
+              method: POST
+              path: "/inspect"
+    binaries:
+      - path: /usr/bin/python*
+      - path: /usr/local/bin/python*
+      - path: /sandbox/.uv/python/*/bin/python*
+"#
+    );
+    file.write_all(policy.as_bytes())
+        .map_err(|error| format!("write policy: {error}"))?;
+    file.flush()
+        .map_err(|error| format!("flush policy: {error}"))?;
+    Ok(file)
+}
+
+#[tokio::test]
+async fn authenticated_middleware_mutates_request_body_and_headers() {
+    let server = start_test_server().await.expect("start upstream server");
+    let policy = write_policy(&server.host, server.port).expect("write middleware policy");
+    let script = format!(
+        r#"import json, urllib.request
+request = urllib.request.Request(
+    "http://{host}:{port}/inspect",
+    data=json.dumps({{"payload": "raw-secret"}}).encode(),
+    headers={{"Content-Type": "application/json"}},
+    method="POST",
+)
+with urllib.request.urlopen(request, timeout=15) as response:
+    print("MIDDLEWARE_RESULT=" + response.read().decode())
+"#,
+        host = server.host,
+        port = server.port,
+    );
+    let policy_path = policy.path().to_string_lossy().into_owned();
+
+    let sandbox = SandboxGuard::create(&["--policy", &policy_path, "--", "python3", "-c", &script])
+        .await
+        .expect("create middleware sandbox");
+    let result = sandbox
+        .create_output
+        .lines()
+        .find_map(|line| line.split_once("MIDDLEWARE_RESULT=").map(|(_, json)| json))
+        .expect("sandbox output should contain the upstream response");
+    let result: Value = serde_json::from_str(result).expect("upstream response should be JSON");
+
+    assert_eq!(result["received_payload"], "[REDACTED]");
+    assert_eq!(result["fixture_header"], "evaluated");
+}
diff --git a/e2e/supervisor-middleware-fixture/Cargo.lock b/e2e/supervisor-middleware-fixture/Cargo.lock
new file mode 100644
index 0000000000..160fb5fd74
--- /dev/null
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diff --git a/e2e/supervisor-middleware-fixture/Cargo.toml b/e2e/supervisor-middleware-fixture/Cargo.toml
new file mode 100644
index 0000000000..f3a6a08e28
--- /dev/null
+++ b/e2e/supervisor-middleware-fixture/Cargo.toml
@@ -0,0 +1,31 @@
+# SPDX-FileCopyrightText: Copyright (c) 2025-2026 NVIDIA CORPORATION & AFFILIATES. All rights reserved.
+# SPDX-License-Identifier: Apache-2.0
+
+# Standalone test fixture. Keeping it out of the root workspace prevents the
+# fixture binary from becoming part of production workspace builds or images.
+[workspace]
+
+[package]
+name = "openshell-e2e-middleware-fixture"
+description = "Authenticated supervisor middleware used only by OpenShell E2E tests"
+version = "0.1.0"
+edition = "2024"
+rust-version = "1.90"
+license = "Apache-2.0"
+publish = false
+
+[dependencies]
+openshell-core = { path = "../../crates/openshell-core", default-features = false }
+openshell-sdk = { path = "../../crates/openshell-sdk", features = ["extension"] }
+tokio = { version = "1.43", features = ["fs", "macros", "rt-multi-thread"] }
+tonic = { version = "0.14", features = ["transport", "tls-ring"] }
+
+[lints.rust]
+unsafe_code = "warn"
+rust_2018_idioms = { level = "warn", priority = -1 }
+
+[lints.clippy]
+all = { level = "warn", priority = -1 }
+pedantic = { level = "warn", priority = -1 }
+module_name_repetitions = "allow"
+missing_errors_doc = "allow"
diff --git a/e2e/supervisor-middleware-fixture/src/main.rs b/e2e/supervisor-middleware-fixture/src/main.rs
new file mode 100644
index 0000000000..0dd7928f56
--- /dev/null
+++ b/e2e/supervisor-middleware-fixture/src/main.rs
@@ -0,0 +1,188 @@
+// SPDX-FileCopyrightText: Copyright (c) 2025-2026 NVIDIA CORPORATION & AFFILIATES. All rights reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+//! Authenticated gRPC middleware used by the focused middleware E2E lane.
+
+use std::net::SocketAddr;
+use std::path::{Path, PathBuf};
+use std::sync::Arc;
+
+use openshell_core::middleware::WebSocketResponseStream;
+use openshell_core::proto::middleware::v1::supervisor_middleware_server::{
+    SupervisorMiddleware, SupervisorMiddlewareServer,
+};
+use openshell_core::proto::{
+    Decision, ExistingHeaderAction, HeaderMutation, HttpRequestEvaluation, HttpRequestResult,
+    MiddlewareBinding, MiddlewareManifest, SupervisorMiddlewareOperation,
+    SupervisorMiddlewarePhase, ValidateConfigRequest, ValidateConfigResponse,
+    WebSocketSessionEvent, WriteHeader, header_mutation,
+};
+use openshell_sdk::extension::{ExtensionCallerKind, GatewayJwtAuthenticator};
+use tonic::transport::{Identity, Server, ServerTlsConfig};
+use tonic::{Request, Response, Status};
+
+const REGISTRATION_NAME: &str = "e2e-scripted";
+const PHASE: SupervisorMiddlewarePhase = SupervisorMiddlewarePhase::PreCredentials;
+const MAX_PAYLOAD_BYTES: u64 = 4 * 1024;
+
+#[derive(Debug)]
+struct Config {
+    listen: SocketAddr,
+    tls_cert: PathBuf,
+    tls_key: PathBuf,
+    gateway_public_key: PathBuf,
+    gateway_key_id: String,
+    gateway_issuer: String,
+    audience: String,
+}
+
+impl Config {
+    fn from_env() -> Result<Self, Box<dyn std::error::Error>> {
+        Ok(Self {
+            listen: required_env("OPENSHELL_E2E_MIDDLEWARE_LISTEN")?.parse()?,
+            tls_cert: required_env("OPENSHELL_E2E_MIDDLEWARE_TLS_CERT")?.into(),
+            tls_key: required_env("OPENSHELL_E2E_MIDDLEWARE_TLS_KEY")?.into(),
+            gateway_public_key: required_env("OPENSHELL_E2E_GATEWAY_PUBLIC_KEY")?.into(),
+            gateway_key_id: required_env("OPENSHELL_E2E_GATEWAY_KEY_ID")?,
+            gateway_issuer: required_env("OPENSHELL_E2E_GATEWAY_ISSUER")?,
+            audience: required_env("OPENSHELL_E2E_MIDDLEWARE_AUDIENCE")?,
+        })
+    }
+}
+
+fn required_env(name: &str) -> Result<String, std::env::VarError> {
+    std::env::var(name)
+}
+
+#[derive(Debug)]
+struct ScriptedMiddleware {
+    authenticator: Arc<GatewayJwtAuthenticator>,
+    audience: String,
+}
+
+impl ScriptedMiddleware {
+    fn authenticate<T>(
+        &self,
+        request: &Request<T>,
+        allowed: &[ExtensionCallerKind],
+    ) -> Result<(), Status> {
+        let caller = self.authenticator.authenticate_request(request)?;
+        if allowed.contains(&caller.kind) {
+            Ok(())
+        } else {
+            Err(Status::permission_denied(
+                "caller kind is not authorized for this middleware RPC",
+            ))
+        }
+    }
+}
+
+#[tonic::async_trait]
+impl SupervisorMiddleware for ScriptedMiddleware {
+    type EvaluateWebSocketSessionStream = WebSocketResponseStream;
+
+    async fn describe(&self, request: Request<()>) -> Result<Response<MiddlewareManifest>, Status> {
+        self.authenticate(
+            &request,
+            &[
+                ExtensionCallerKind::Gateway,
+                ExtensionCallerKind::Supervisor,
+            ],
+        )?;
+        Ok(Response::new(MiddlewareManifest {
+            name: "openshell-e2e-middleware-fixture".into(),
+            service_version: env!("CARGO_PKG_VERSION").into(),
+            bindings: vec![MiddlewareBinding {
+                operation: SupervisorMiddlewareOperation::HttpRequest as i32,
+                phase: PHASE as i32,
+                max_payload_bytes: MAX_PAYLOAD_BYTES,
+                timeout: String::new(),
+            }],
+            expected_audience: self.audience.clone(),
+        }))
+    }
+
+    async fn validate_config(
+        &self,
+        request: Request<ValidateConfigRequest>,
+    ) -> Result<Response<ValidateConfigResponse>, Status> {
+        self.authenticate(&request, &[ExtensionCallerKind::Gateway])?;
+        let valid = request.get_ref().middleware_name == REGISTRATION_NAME;
+        Ok(Response::new(ValidateConfigResponse {
+            valid,
+            reason: if valid {
+                String::new()
+            } else {
+                "unsupported middleware registration".into()
+            },
+        }))
+    }
+
+    async fn evaluate_http_request(
+        &self,
+        request: Request<HttpRequestEvaluation>,
+    ) -> Result<Response<HttpRequestResult>, Status> {
+        self.authenticate(&request, &[ExtensionCallerKind::Supervisor])?;
+        let request = request.into_inner();
+        if request.middleware_name != REGISTRATION_NAME || request.phase != PHASE as i32 {
+            return Err(Status::invalid_argument(
+                "unsupported middleware registration or phase",
+            ));
+        }
+
+        let body = String::from_utf8(request.body)
+            .map_err(|_| Status::invalid_argument("fixture requires a UTF-8 request body"))?;
+        let replacement = body.replace("raw-secret", "[REDACTED]");
+        Ok(Response::new(HttpRequestResult {
+            decision: Decision::Allow as i32,
+            body: replacement.into_bytes(),
+            has_body: true,
+            header_mutations: vec![HeaderMutation {
+                operation: Some(header_mutation::Operation::Write(WriteHeader {
+                    name: "x-openshell-middleware-fixture".into(),
+                    value: "evaluated".into(),
+                    on_existing: ExistingHeaderAction::Overwrite as i32,
+                })),
+            }],
+            ..Default::default()
+        }))
+    }
+
+    async fn evaluate_web_socket_session(
+        &self,
+        _request: Request<tonic::Streaming<WebSocketSessionEvent>>,
+    ) -> Result<Response<Self::EvaluateWebSocketSessionStream>, Status> {
+        Err(Status::unimplemented(
+            "the HTTP-only E2E fixture does not implement WebSocket middleware",
+        ))
+    }
+}
+
+async fn read(path: &Path) -> Result<Vec<u8>, std::io::Error> {
+    tokio::fs::read(path).await
+}
+
+#[tokio::main]
+async fn main() -> Result<(), Box<dyn std::error::Error>> {
+    let config = Config::from_env()?;
+    let cert = read(&config.tls_cert).await?;
+    let key = read(&config.tls_key).await?;
+    let public_key = read(&config.gateway_public_key).await?;
+    let authenticator = GatewayJwtAuthenticator::from_ed25519_pem(
+        &public_key,
+        config.gateway_key_id,
+        config.gateway_issuer,
+        config.audience.clone(),
+    )?;
+    let service = ScriptedMiddleware {
+        authenticator: Arc::new(authenticator),
+        audience: config.audience,
+    };
+
+    Server::builder()
+        .tls_config(ServerTlsConfig::new().identity(Identity::from_pem(cert, key)))?
+        .add_service(SupervisorMiddlewareServer::new(service))
+        .serve(config.listen)
+        .await?;
+    Ok(())
+}
diff --git a/e2e/with-docker-gateway.sh b/e2e/with-docker-gateway.sh
index 15e9d3466e..259bbf9318 100755
--- a/e2e/with-docker-gateway.sh
+++ b/e2e/with-docker-gateway.sh
@@ -113,6 +113,11 @@ E2E_NAMESPACE=""
 DOCKER_NETWORK_NAME=""
 DOCKER_NETWORK_CONNECTED_CONTAINER=""
 DOCKER_NETWORK_MANAGED=0
+MIDDLEWARE_FIXTURE_PID=""
+MIDDLEWARE_FIXTURE_LOG="${WORKDIR}/middleware-fixture.log"
+MIDDLEWARE_FIXTURE_ENDPOINT=""
+MIDDLEWARE_FIXTURE_CA_CERT=""
+MIDDLEWARE_FIXTURE_AUDIENCE="urn:openshell:extension:middleware:e2e-scripted"
 GPU_MODE="${OPENSHELL_E2E_DOCKER_GPU:-0}"
 OIDC_MODE="${OPENSHELL_E2E_OIDC_GATEWAY:-0}"
 OIDC_ISSUER="${OPENSHELL_E2E_OIDC_ISSUER:-}"
@@ -135,6 +140,18 @@ cleanup() {
 
   e2e_stop_gateway "${GATEWAY_PID}" "${GATEWAY_PID_FILE}"
 
+  if [ -n "${MIDDLEWARE_FIXTURE_PID}" ] \
+     && kill -0 "${MIDDLEWARE_FIXTURE_PID}" 2>/dev/null; then
+    kill "${MIDDLEWARE_FIXTURE_PID}" 2>/dev/null || true
+    wait "${MIDDLEWARE_FIXTURE_PID}" 2>/dev/null || true
+  fi
+
+  if [ "${exit_code}" -ne 0 ] && [ -s "${MIDDLEWARE_FIXTURE_LOG}" ]; then
+    echo "=== supervisor middleware fixture log ==="
+    cat "${MIDDLEWARE_FIXTURE_LOG}"
+    echo "=== end supervisor middleware fixture log ==="
+  fi
+
   if [ "${exit_code}" -ne 0 ] \
      && [ -n "${E2E_NAMESPACE}" ] \
      && command -v docker >/dev/null 2>&1; then
@@ -251,6 +268,104 @@ connect_current_container_to_docker_network() {
   GATEWAY_HOST_ALIAS_IP="${container_ip}"
 }
 
+# Build and launch an authenticated TLS extension service that is reachable
+# from the host gateway and sandbox containers. The focused middleware E2E lane
+# opts into this fixture; other Docker E2E callers retain the existing setup.
+start_middleware_fixture() {
+  local manifest="${ROOT}/e2e/supervisor-middleware-fixture/Cargo.toml"
+  local binary="${TARGET_DIR}/debug/openshell-e2e-middleware-fixture"
+  local fixture_dir="${STATE_DIR}/middleware-fixture"
+  local fixture_host
+  local fixture_port
+
+  echo "Building authenticated supervisor middleware E2E fixture..."
+  CARGO_TARGET_DIR="${TARGET_DIR}" cargo build --locked --manifest-path "${manifest}"
+
+  if [ -n "${GATEWAY_HOST_ALIAS_IP}" ]; then
+    # In GitHub Actions, the fixture and gateway run in the job container. The
+    # wrapper has already attached that container to the sandbox network.
+    fixture_host="${GATEWAY_HOST_ALIAS_IP}"
+  elif [ "$(uname -s)" = "Linux" ]; then
+    # In a native Linux run, the fixture and gateway run on the host. The
+    # bridge gateway address is reachable from both the host and containers.
+    fixture_host="$(docker network inspect \
+      --format '{{(index .IPAM.Config 0).Gateway}}' \
+      "${DOCKER_NETWORK_NAME}")"
+  else
+    echo "ERROR: supervisor middleware E2E currently supports GitHub Actions and native Linux Docker." >&2
+    return 2
+  fi
+
+  if [ -z "${fixture_host}" ]; then
+    echo "ERROR: failed to determine a supervisor middleware fixture address." >&2
+    return 2
+  fi
+
+  mkdir -p "${fixture_dir}"
+  # Generate a one-run CA and a CA-signed server certificate whose IP SAN
+  # matches the shared address used by the gateway and sandbox supervisor.
+  openssl req -x509 -newkey rsa:2048 -nodes \
+    -keyout "${fixture_dir}/ca.key" \
+    -out "${fixture_dir}/ca.crt" \
+    -days 1 \
+    -subj "/CN=OpenShell middleware E2E CA" \
+    -addext "basicConstraints=critical,CA:TRUE" \
+    -addext "keyUsage=critical,keyCertSign,cRLSign" >/dev/null 2>&1
+  openssl req -newkey rsa:2048 -nodes \
+    -keyout "${fixture_dir}/tls.key" \
+    -out "${fixture_dir}/tls.csr" \
+    -subj "/CN=${fixture_host}" >/dev/null 2>&1
+  {
+    printf 'basicConstraints=critical,CA:FALSE\n'
+    printf 'keyUsage=critical,digitalSignature,keyEncipherment\n'
+    printf 'extendedKeyUsage=serverAuth\n'
+    printf 'subjectAltName=IP:%s\n' "${fixture_host}"
+  } >"${fixture_dir}/tls.ext"
+  openssl x509 -req \
+    -in "${fixture_dir}/tls.csr" \
+    -CA "${fixture_dir}/ca.crt" \
+    -CAkey "${fixture_dir}/ca.key" \
+    -CAcreateserial \
+    -out "${fixture_dir}/tls.crt" \
+    -days 1 \
+    -extfile "${fixture_dir}/tls.ext" >/dev/null 2>&1
+  MIDDLEWARE_FIXTURE_CA_CERT="${fixture_dir}/ca.crt"
+
+  fixture_port="$(e2e_pick_port)"
+  echo "Starting supervisor middleware E2E fixture on ${fixture_host}:${fixture_port}..."
+  # Give the fixture both sides of the trust relationship: its TLS identity and
+  # the gateway identity/audience required to verify extension bearer tokens.
+  OPENSHELL_E2E_MIDDLEWARE_LISTEN="0.0.0.0:${fixture_port}" \
+  OPENSHELL_E2E_MIDDLEWARE_TLS_CERT="${fixture_dir}/tls.crt" \
+  OPENSHELL_E2E_MIDDLEWARE_TLS_KEY="${fixture_dir}/tls.key" \
+  OPENSHELL_E2E_GATEWAY_PUBLIC_KEY="${JWT_DIR}/public.pem" \
+  OPENSHELL_E2E_GATEWAY_KEY_ID="$(tr -d '\r\n' <"${JWT_DIR}/kid")" \
+  OPENSHELL_E2E_GATEWAY_ISSUER="openshell-gateway:openshell-e2e-docker-${HOST_PORT}" \
+  OPENSHELL_E2E_MIDDLEWARE_AUDIENCE="${MIDDLEWARE_FIXTURE_AUDIENCE}" \
+    "${binary}" >"${MIDDLEWARE_FIXTURE_LOG}" 2>&1 &
+  MIDDLEWARE_FIXTURE_PID=$!
+
+  # A TCP readiness probe is sufficient here: the gateway performs the
+  # authenticated gRPC Describe call when it starts immediately afterward.
+  local attempt
+  for attempt in $(seq 1 100); do
+    if ! kill -0 "${MIDDLEWARE_FIXTURE_PID}" 2>/dev/null; then
+      echo "ERROR: supervisor middleware E2E fixture exited before becoming ready." >&2
+      cat "${MIDDLEWARE_FIXTURE_LOG}" >&2 || true
+      return 1
+    fi
+    if python3 -c "import socket; s=socket.create_connection(('127.0.0.1', ${fixture_port}), 0.2); s.close()" 2>/dev/null; then
+      MIDDLEWARE_FIXTURE_ENDPOINT="https://${fixture_host}:${fixture_port}"
+      echo "Supervisor middleware E2E fixture ready at ${MIDDLEWARE_FIXTURE_ENDPOINT}."
+      return 0
+    fi
+    sleep 0.2
+  done
+
+  echo "ERROR: supervisor middleware E2E fixture did not become ready within 20s." >&2
+  return 1
+}
+
 if [ -n "${OPENSHELL_GATEWAY_ENDPOINT:-}" ]; then
   case "${OPENSHELL_GATEWAY_ENDPOINT}" in
     http://*) ;;
@@ -469,6 +584,11 @@ fi
 echo "Starting openshell-gateway on port ${HOST_PORT} (namespace: ${E2E_NAMESPACE})..."
 echo "Using sandbox image: ${SANDBOX_IMAGE} (pull policy: ${SANDBOX_IMAGE_PULL_POLICY})"
 e2e_generate_gateway_jwt "${JWT_DIR}"
+if [ "${OPENSHELL_E2E_MIDDLEWARE_FIXTURE:-0}" = "1" ]; then
+  # The gateway validates middleware with Describe during startup, so the
+  # extension service and its trust material must exist first.
+  start_middleware_fixture
+fi
 
 # Driver-specific options moved from CLI flags into a TOML config table
 # (commit 560550d2). Synthesize a minimal config here and pass --config.
@@ -494,6 +614,17 @@ GATEWAY_CONFIG="${STATE_DIR}/gateway.toml"
       e2e_write_gateway_oidc_config "${OPENSHELL_OIDC_ISSUER}"
     fi
   fi
+  if [ -n "${MIDDLEWARE_FIXTURE_ENDPOINT}" ]; then
+    # Register only the opt-in fixture, pinning its ephemeral CA and the exact
+    # audience that both the gateway token issuer and fixture verifier expect.
+    printf '[[openshell.supervisor.middleware]]\n'
+    printf 'name = "e2e-scripted"\n'
+    printf 'grpc_endpoint = %s\n' "$(toml_string "${MIDDLEWARE_FIXTURE_ENDPOINT}")"
+    printf 'tls_ca_cert_path = %s\n' "$(toml_string "${MIDDLEWARE_FIXTURE_CA_CERT}")"
+    printf 'audience = %s\n' "$(toml_string "${MIDDLEWARE_FIXTURE_AUDIENCE}")"
+    printf 'max_payload_bytes = 4096\n'
+    printf 'timeout = "500ms"\n\n'
+  fi
   printf '[openshell.drivers.docker]\n'
   printf 'sandbox_namespace = %s\n'    "$(toml_string "${E2E_NAMESPACE}")"
   printf 'network_name = %s\n'         "$(toml_string "${DOCKER_NETWORK_NAME}")"
diff --git a/tasks/test.toml b/tasks/test.toml
index bef8baf2b5..474eb4d40a 100644
--- a/tasks/test.toml
+++ b/tasks/test.toml
@@ -92,6 +92,12 @@ run = [
   "e2e/with-docker-gateway.sh cargo test --manifest-path e2e/rust/Cargo.toml --features e2e-docker --test websocket_conformance",
 ]
 
+["e2e:supervisor-middleware"]
+description = "Run the authenticated supervisor middleware happy-path E2E test against a Docker-backed gateway"
+run = [
+  "OPENSHELL_E2E_MIDDLEWARE_FIXTURE=1 e2e/with-docker-gateway.sh cargo test --manifest-path e2e/rust/Cargo.toml --features e2e-docker --test supervisor_middleware -- --nocapture",
+]
+
 ["e2e:mcp"]
 description = "Run MCP conformance e2e scenarios against one Docker-backed gateway (static defaults for spec 2025-11-25; set OPENSHELL_MCP_CONFORMANCE_SCENARIOS for a focused subset)"
 run = "bash e2e/mcp-conformance.sh"