TLS: fingerprint-confirm flow for self-signed gateway certs (issue #14)

docs/09 §9.4 promised a SSH-host-key-style fingerprint confirm on first pair, but the app built a default OkHttpClient with no certificate handling — self-signed gateway certs were simply rejected. Build the flow: - TlsPinning.kt: PinningTrustManager wraps the platform default trust manager; a rejected cert is accepted only when its SHA-256 fingerprint matches the user-confirmed pin, anything else fails with TlsFingerprintRequired (hostname verification still applies). - SecureStore.pinnedCertFingerprint (Android EncryptedSharedPreferences + desktop settings.json), cleared on forget(). - GatewayClient: pinning socket factory on the shared client (all legs inherit it), new terminal State.TlsConfirmRequired, unwrap the nested TlsFingerprintRequired in connect loop / watchdog / SSE / poll / testHello. - ConnectScreen: confirm dialog showing the fingerprint ("Confirm & pin" re-runs the connect); IrisApp routes TlsConfirmRequired there; ChatScreen + desktop tray handle the new state. - Docs: §9.4 now describes the real flow (incl. SAN requirement), gap table item 6 → implemented, setup.md limitation note updated. - Tests: TlsPinningTest (fingerprint vs openssl, pin accept/reject, live pin read, unwrap) + TlsPinningIntegrationTest (real TLS handshake: unpinned → confirm data, pinned → 200). Live E2E verified on the phone: first pair against a self-signed IRIS_HTTP_CERT gateway shows the dialog, confirm pins, chat works, auto-reconnect after gateway restart uses the pin.
2026-08-24 21:30:42 +02:00
1 parent f90e40a3fc
commit 597a28050f
@@ -19,9 +19,12 @@ import iris.IrisApp
 import iris.net.GatewayClient
 import iris.platform.DesktopBridge
 import iris.platform.DesktopSecureStore
+import kotlinx.coroutines.delay
+import kotlinx.serialization.json.Json
+import kotlinx.serialization.json.jsonObject
+import kotlinx.serialization.json.jsonPrimitive
 import java.awt.Color
 import java.awt.Graphics2D
-import javax.imageio.ImageIO
 import java.awt.RenderingHints
 import java.awt.SystemTray
 import java.awt.event.WindowEvent
@@ -29,10 +32,7 @@ import java.awt.event.WindowFocusListener
 import java.awt.image.BufferedImage
 import java.io.File
 import java.util.concurrent.atomic.AtomicBoolean
-import kotlinx.coroutines.delay
-import kotlinx.serialization.json.Json
-import kotlinx.serialization.json.jsonObject
-import kotlinx.serialization.json.jsonPrimitive
+import javax.imageio.ImageIO

 /**
 * M6: desktop shell (docs/11 §11.2/§11.3).
@@ -48,6 +48,7 @@ private val windowJson = File(System.getProperty("user.home"), ".iris/window.jso

 // Window/taskbar icon (src/main/resources/icon.png).
 private class IrisDesktop
+
 private val windowIcon = ImageIO.read(IrisDesktop::class.java.getResource("/icon.png")!!).toComposeImageBitmap()

 // Tray icon colors (ARGB). .toInt(): the literals exceed the Int range.
@@ -87,15 +88,37 @@ fun main() {
        LaunchedEffect(Unit) {
            while (true) {
                delay(2_000)
-                val state = DesktopBridge.controller?.client?.state?.value
-                val (color, tooltip) = when (state) {
-                    null,
-                    is GatewayClient.State.Disconnected -> TRAY_OFFLINE to "Iris — offline"
-                    is GatewayClient.State.Connecting,
-                    is GatewayClient.State.Reconnecting -> TRAY_CONNECTING to "Iris — connecting…"
-                    is GatewayClient.State.Connected -> TRAY_CONNECTED to "Iris — connected"
-                    is GatewayClient.State.AuthFailed -> TRAY_AUTH_FAILED to "Iris — auth failed"
-                }
+                val state =
+                    DesktopBridge.controller
+                        ?.client
+                        ?.state
+                        ?.value
+                val (color, tooltip) =
+                    when (state) {
+                        null,
+                        is GatewayClient.State.Disconnected,
+                        -> {
+                            TRAY_OFFLINE to "Iris — offline"
+                        }
+
+                        is GatewayClient.State.Connecting,
+                        is GatewayClient.State.Reconnecting,
+                        -> {
+                            TRAY_CONNECTING to "Iris — connecting…"
+                        }
+
+                        is GatewayClient.State.Connected -> {
+                            TRAY_CONNECTED to "Iris — connected"
+                        }
+
+                        is GatewayClient.State.AuthFailed -> {
+                            TRAY_AUTH_FAILED to "Iris — auth failed"
+                        }
+
+                        is GatewayClient.State.TlsConfirmRequired -> {
+                            TRAY_AUTH_FAILED to "Iris — gateway certificate needs confirmation"
+                        }
+                    }
                trayColor = color
                trayTooltip = tooltip
            }
@@ -126,15 +149,17 @@ fun main() {
            state = loadWindowState(),
        ) {
            composeWindow = window
-            window.addWindowFocusListener(object : WindowFocusListener {
-                override fun windowGainedFocus(e: WindowEvent) {
-                    DesktopBridge.foreground = true
-                }
+            window.addWindowFocusListener(
+                object : WindowFocusListener {
+                    override fun windowGainedFocus(e: WindowEvent) {
+                        DesktopBridge.foreground = true
+                    }

-                override fun windowLostFocus(e: WindowEvent) {
-                    DesktopBridge.foreground = false
-                }
-            })
+                    override fun windowLostFocus(e: WindowEvent) {
+                        DesktopBridge.foreground = false
+                    }
+                },
+            )
            IrisApp(store)
        }
    }
@@ -187,4 +212,4 @@ private fun saveWindowState(window: ComposeWindow?) {
        )
    } catch (_: Exception) {
    }
-}
+}
@@ -80,6 +80,10 @@ class AndroidSecureStore(
        get() = prefs.getString(KEY_DEVICE_TOKEN, "").orEmpty()
        set(value) = prefs.edit().putString(KEY_DEVICE_TOKEN, value.trim()).apply()

+    override var pinnedCertFingerprint: String
+        get() = prefs.getString(KEY_PINNED_CERT, "").orEmpty()
+        set(value) = prefs.edit().putString(KEY_PINNED_CERT, value.trim()).apply()
+
    override val deviceId: String
        get() {
            var id = prefs.getString(KEY_DEVICE_ID, null)
@@ -201,6 +205,7 @@ class AndroidSecureStore(
            .remove(KEY_NTFY_TOPIC)
            .remove(KEY_NTFY_SERVER)
            .remove(KEY_PUSH_BACKEND)
+            .remove(KEY_PINNED_CERT)
            .apply()
    }

@@ -216,6 +221,7 @@ class AndroidSecureStore(
        const val KEY_NTFY_TOPIC = "ntfy_topic"
        const val KEY_NTFY_SERVER = "ntfy_server"
        const val KEY_PUSH_BACKEND = "push_backend"
+        const val KEY_PINNED_CERT = "pinned_cert_fingerprint"
        const val KEY_THREADS_ENABLED = "threads_enabled"
        const val KEY_TOOL_DETAIL = "tool_detail"
        const val KEY_STREAMING_ENABLED = "streaming_enabled"
@@ -121,6 +121,21 @@ fun IrisApp(
                            }
                        }

+                        // TLS: the gateway's certificate is untrusted and not
+                        // the pinned one (docs/09 §9.4) — ask the user to
+                        // confirm its fingerprint (SSH host-key style).
+                        is GatewayClient.State.TlsConfirmRequired -> {
+                            key(deepLinkPair) {
+                                ConnectScreen(
+                                    controller,
+                                    prefillUrl = pairUrl,
+                                    prefillToken = pairToken,
+                                    initialError = "Gateway certificate needs confirmation — verify its fingerprint on the gateway host, then confirm below.",
+                                    tlsFingerprint = s.fingerprint,
+                                )
+                            }
+                        }
+
                        // Connecting / Reconnecting / Connected all render the chat; the header
                        // status bubble + connection banner show the link state
                        // without blocking the view (M7's full-screen spinner is gone).
@@ -17,6 +17,11 @@ interface SecureStore {
     *  gateway can revoke it per device. Empty until the first hello.ack. */
    var deviceToken: String

+    /** SHA-256 fingerprint (colon-separated pairs) of the gateway's TLS
+     *  certificate, confirmed by the user on first pair (docs/09 §9.4).
+     *  Empty = nothing pinned (CA-signed certs need no pin). */
+    var pinnedCertFingerprint: String
+
    /** Stable app-generated device id (persisted). */
    val deviceId: String

@@ -67,6 +67,13 @@ class GatewayClient(
        data class AuthFailed(
            val message: String,
        ) : State
+
+        /** The gateway's TLS certificate is untrusted and doesn't match the
+         *  pinned fingerprint (docs/09 §9.4). Terminal: the connect loop
+         *  stops and the UI asks the user to confirm the fingerprint. */
+        data class TlsConfirmRequired(
+            val fingerprint: String,
+        ) : State
    }

    private val _state = MutableStateFlow<State>(State.Disconnected)
@@ -79,10 +86,18 @@ class GatewayClient(
    private val _events = MutableSharedFlow<Frame>(extraBufferCapacity = 128)
    val events: SharedFlow<Frame> = _events.asSharedFlow()

+    // TLS: the pinning trust manager wraps the platform default (CA-signed
+    // certs behave as before); a self-signed gateway cert is accepted only
+    // after the user confirms its fingerprint (docs/09 §9.4). The pin is
+    // read live from the store so a fresh confirm takes effect without
+    // rebuilding the client.
+    private val pinningTm = PinningTrustManager { store.pinnedCertFingerprint }
+
    private val client: OkHttpClient =
        OkHttpClient
            .Builder()
            .pingInterval(20, TimeUnit.SECONDS)
+            .sslSocketFactory(pinningSslSocketFactory(pinningTm), pinningTm)
            .build()

    private var connectJob: Job? = null
@@ -210,6 +225,7 @@ class GatewayClient(
                try {
                    gw.health()
                } catch (e: Exception) {
+                    if (failTls(e)) return
                    false
                }
            if (!healthOk) {
@@ -247,6 +263,10 @@ class GatewayClient(
                        try {
                            gw.health()
                        } catch (e: Exception) {
+                            if (failTls(e)) {
+                                receiveJob.cancel()
+                                break
+                            }
                            false
                        }
                    probeFailures = if (ok) 0 else probeFailures + 1
@@ -267,8 +287,9 @@ class GatewayClient(
                }
                receiveJob.join()
            }
-            // Terminal auth failure: don't redial with the same bad token.
-            if (_state.value is State.AuthFailed) return
+            // Terminal failures: don't redial with the same bad token / the
+            // same untrusted certificate (the UI asks the user to act).
+            if (_state.value is State.AuthFailed || _state.value is State.TlsConfirmRequired) return
        }
    }

@@ -316,6 +337,7 @@ class GatewayClient(
                    _state.value = State.AuthFailed("gateway rejected the pairing token (HTTP 401)")
                    return
                } catch (e: Exception) {
+                    if (failTls(e)) return
                    markStreamLost()
                    IrisLog.w("http poll failed: ${e.message}")
                    delay(backoff)
@@ -342,6 +364,7 @@ class GatewayClient(
                    _state.value = State.AuthFailed("gateway rejected the pairing token (HTTP 401)")
                    return
                } catch (e: Exception) {
+                    if (failTls(e)) return
                    sseFailures++
                    markStreamLost()
                    if (sseFailures >= 2) {
@@ -422,6 +445,17 @@ class GatewayClient(
        }
    }

+    /** Terminal TLS failure: the presented certificate is untrusted and not
+     *  the pinned one (docs/09 §9.4). Retry can't succeed — stop the connect
+     *  loop and let the UI ask the user to confirm the fingerprint. True when
+     *  the state was set. */
+    private fun failTls(e: Exception): Boolean {
+        val tls = tlsFingerprintRequired(e) ?: return false
+        IrisLog.w("tls: untrusted gateway certificate (fingerprint ${tls.fingerprint})")
+        _state.value = State.TlsConfirmRequired(tls.fingerprint)
+        return true
+    }
+
    // ── Outbound ──────────────────────────────────────────────────────────

    /** Send a text message (fire-and-forget; the server echoes it back).
@@ -574,13 +608,15 @@ class GatewayClient(
                } catch (e: CancellationException) {
                    throw e
                } catch (e: Exception) {
-                    Result.failure(IllegalStateException("connection failed: ${e.message}"))
+                    // Unwrap the pinning manager's signal so the Connect
+                    // screen can offer the fingerprint confirm dialog.
+                    Result.failure(tlsFingerprintRequired(e) ?: IllegalStateException("connection failed: ${e.message}"))
                } finally {
                    job.cancel()
                }
            }
        } catch (e: Exception) {
-            Result.failure(e)
+            Result.failure(tlsFingerprintRequired(e) ?: e)
        }
    }

@@ -0,0 +1,118 @@
+package iris.net
+
+import java.security.KeyStore
+import java.security.MessageDigest
+import java.security.SecureRandom
+import java.security.cert.CertificateException
+import java.security.cert.X509Certificate
+import javax.net.ssl.SSLContext
+import javax.net.ssl.SSLSocketFactory
+import javax.net.ssl.TrustManager
+import javax.net.ssl.TrustManagerFactory
+import javax.net.ssl.X509TrustManager
+
+/**
+ * TLS certificate pinning for self-signed gateways (docs/09 §9.4).
+ *
+ * A gateway behind `IRIS_HTTP_CERT`/`IRIS_WS_CERT` may present a
+ * self-signed certificate the platform doesn't trust. Instead of forcing the
+ * user to install it into the system trust store, the app shows the
+ * certificate's SHA-256 fingerprint on first pair (SSH host-key style); once
+ * the user confirms it, the fingerprint is pinned in secure storage and
+ * [PinningTrustManager] accepts exactly that certificate from then on.
+ *
+ * Hostname verification is NOT bypassed: OkHttp runs its own hostname check
+ * on top of the trust manager, so a pinned cert still has to match the URL's
+ * host. A *changed* certificate (different fingerprint) fails again with
+ * [TlsFingerprintRequired] — the user must re-confirm, like a changed SSH
+ * host key.
+ */
+
+/**
+ * The gateway presented a certificate the platform doesn't trust and that
+ * doesn't match the pinned fingerprint. Carries the SHA-256 fingerprint the
+ * user must confirm. Thrown by [PinningTrustManager] during the handshake;
+ * the JSSE/OkHttp layers wrap it, so find it with [tlsFingerprintRequired].
+ */
+class TlsFingerprintRequired(
+    val fingerprint: String,
+) : CertificateException("gateway certificate not trusted (fingerprint $fingerprint)")
+
+/**
+ * SHA-256 of the certificate's DER encoding, colon-separated byte pairs
+ * (SSH host-key style) — the string the user verifies on the gateway host.
+ */
+fun certFingerprint(cert: X509Certificate): String =
+    MessageDigest
+        .getInstance("SHA-256")
+        .digest(cert.encoded)
+        .joinToString(":") { String.format("%02X", it) }
+
+/**
+ * Wraps the platform default trust manager:
+ * - CA-signed certs behave exactly as before (the default manager decides).
+ * - A cert the default manager REJECTS is accepted only when its fingerprint
+ *   equals the user-confirmed pin ([pinnedFingerprint], read live so a fresh
+ *   pin is picked up without rebuilding the client).
+ * - Anything else fails with [TlsFingerprintRequired] carrying the
+ *   presented fingerprint, so the UI can offer the confirm dialog.
+ */
+class PinningTrustManager(
+    private val pinnedFingerprint: () -> String,
+) : X509TrustManager {
+    private val default: X509TrustManager = defaultTrustManager()
+
+    override fun checkClientTrusted(
+        chain: Array<X509Certificate>,
+        authType: String,
+    ) {
+        default.checkClientTrusted(chain, authType)
+    }
+
+    override fun getAcceptedIssuers(): Array<X509Certificate> = default.acceptedIssuers
+
+    override fun checkServerTrusted(
+        chain: Array<X509Certificate>,
+        authType: String,
+    ) {
+        try {
+            default.checkServerTrusted(chain, authType)
+        } catch (e: CertificateException) {
+            val fp = certFingerprint(chain.first())
+            if (pinnedFingerprint().isNotBlank() && fp == pinnedFingerprint()) return
+            throw TlsFingerprintRequired(fp)
+        }
+    }
+}
+
+/** The platform default server trust manager (the JDK's CA store). */
+fun defaultTrustManager(): X509TrustManager {
+    val factory = TrustManagerFactory.getInstance(TrustManagerFactory.getDefaultAlgorithm())
+    factory.init(null as KeyStore?)
+    return (factory.trustManagers.firstOrNull { it is X509TrustManager } as? X509TrustManager)
+        ?: error("no X509TrustManager in the default trust store")
+}
+
+/** An [SSLSocketFactory] that trusts via [tm] (the pinning manager). */
+fun pinningSslSocketFactory(tm: X509TrustManager): SSLSocketFactory {
+    val ctx = SSLContext.getInstance("TLS")
+    ctx.init(null, arrayOf<TrustManager>(tm), SecureRandom())
+    return ctx.socketFactory
+}
+
+/**
+ * Unwrap a [TlsFingerprintRequired] from a (possibly nested) transport
+ * exception: the trust manager throws it during the handshake and the
+ * JSSE/OkHttp layers wrap it in SSLHandshakeException/IOException. Null when
+ * the failure has nothing to do with an untrusted gateway certificate.
+ */
+fun tlsFingerprintRequired(e: Throwable): TlsFingerprintRequired? {
+    var t: Throwable? = e
+    var depth = 0
+    while (t != null && depth < 10) {
+        if (t is TlsFingerprintRequired) return t
+        t = t.cause
+        depth++
+    }
+    return null
+}
@@ -1307,6 +1307,14 @@ class IrisController(
        return Result.success(Unit)
    }

+    /** TLS fingerprint confirm (docs/09 §9.4): pin the gateway's presented
+     *  certificate so its self-signed cert is accepted from now on. The
+     *  caller re-runs [connect] (or the connect loop picks the pin up on its
+     *  next attempt — the trust manager reads the store live). */
+    fun confirmTlsFingerprint(fingerprint: String) {
+        store.pinnedCertFingerprint = fingerprint
+    }
+
    fun forget() {
        store.clear()
        // A different gateway means a different chat universe — wipe the cache.
@@ -2100,6 +2100,7 @@ private fun statusLabel(state: GatewayClient.State): String =
        GatewayClient.State.Reconnecting -> "reconnecting…"
        is GatewayClient.State.Connected -> "connected"
        is GatewayClient.State.AuthFailed -> "auth failed"
+        is GatewayClient.State.TlsConfirmRequired -> "cert confirm needed"
    }

 /** M6: command palette (Ctrl/Cmd+K) — all actions, filterable. */
@@ -2385,6 +2386,7 @@ private fun statusToastText(state: GatewayClient.State): String =
        GatewayClient.State.Reconnecting -> "Re-Connecting to Hermes"
        GatewayClient.State.Disconnected -> "Unpaired from Hermes"
        is GatewayClient.State.AuthFailed -> "Unpaired from Hermes"
+        is GatewayClient.State.TlsConfirmRequired -> "Gateway certificate needs confirmation"
    }

 /** Header status bubble: green = connected, yellow pulsing = (re)connecting,
@@ -2405,6 +2407,7 @@ private fun StatusBubble(

            GatewayClient.State.Disconnected,
            is GatewayClient.State.AuthFailed,
+            is GatewayClient.State.TlsConfirmRequired,
            -> IrisColors.statusRed to false
        }
    val alpha = remember { Animatable(1f) }
@@ -11,10 +11,12 @@ import androidx.compose.foundation.rememberScrollState
 import androidx.compose.foundation.shape.RoundedCornerShape
 import androidx.compose.foundation.text.KeyboardOptions
 import androidx.compose.foundation.verticalScroll
+import androidx.compose.material3.AlertDialog
 import androidx.compose.material3.Button
 import androidx.compose.material3.MaterialTheme
 import androidx.compose.material3.OutlinedTextField
 import androidx.compose.material3.Text
+import androidx.compose.material3.TextButton
 import androidx.compose.runtime.Composable
 import androidx.compose.runtime.getValue
 import androidx.compose.runtime.mutableStateOf
@@ -24,9 +26,11 @@ import androidx.compose.runtime.setValue
 import androidx.compose.ui.Alignment
 import androidx.compose.ui.Modifier
 import androidx.compose.ui.draw.clip
+import androidx.compose.ui.text.font.FontFamily
 import androidx.compose.ui.text.input.KeyboardType
 import androidx.compose.ui.text.input.PasswordVisualTransformation
 import androidx.compose.ui.unit.dp
+import iris.net.TlsFingerprintRequired
 import iris.platform.QrScanButton
 import iris.platform.isDesktop
 import iris.state.IrisController
@@ -44,6 +48,9 @@ fun ConnectScreen(
    prefillUrl: String = "",
    prefillToken: String = "",
    initialError: String? = null,
+    /** Gateway certificate fingerprint awaiting user confirmation (docs/09
+     *  §9.4) — shown as a confirm dialog on entry. */
+    tlsFingerprint: String? = null,
 ) {
    val scope = rememberCoroutineScope()
    // Default is a cleartext (non-TLS) URL because the typical gateway is on
@@ -52,6 +59,31 @@ fun ConnectScreen(
    var token by remember { mutableStateOf(prefillToken) }
    var busy by remember { mutableStateOf(false) }
    var error by remember { mutableStateOf(initialError) }
+    // Fingerprint the user still has to confirm (self-signed gateway cert,
+    // docs/09 §9.4): set on entry (TlsConfirmRequired state) or when a
+    // connect attempt fails with an untrusted certificate.
+    var pendingFingerprint by remember { mutableStateOf(tlsFingerprint) }
+
+    // "Test & Connect" (also the dialog's confirm action): real hello test,
+    // then save + (re)connect. An untrusted gateway certificate surfaces as
+    // the fingerprint confirm dialog instead of a plain error.
+    fun doConnect() {
+        if (busy) return
+        busy = true
+        error = null
+        scope.launch {
+            val result = controller.connect(url.trim(), token.trim())
+            busy = false
+            if (result.isFailure) {
+                val ex = result.exceptionOrNull()
+                if (ex is TlsFingerprintRequired) {
+                    pendingFingerprint = ex.fingerprint
+                } else {
+                    error = ex?.message ?: "connection failed"
+                }
+            }
+        }
+    }

    Column(
        modifier =
@@ -116,18 +148,7 @@ fun ConnectScreen(
            Spacer(modifier = Modifier.height(24.dp))

            Button(
-                onClick = {
-                    if (busy) return@Button
-                    busy = true
-                    error = null
-                    scope.launch {
-                        val result = controller.connect(url.trim(), token.trim())
-                        busy = false
-                        if (result.isFailure) {
-                            error = result.exceptionOrNull()?.message ?: "connection failed"
-                        }
-                    }
-                },
+                onClick = { doConnect() },
                enabled = !busy,
                modifier = Modifier.fillMaxWidth(),
            ) {
@@ -152,4 +173,43 @@ fun ConnectScreen(
            color = MaterialTheme.colorScheme.onSurfaceVariant,
        )
    }
+
+    // Fingerprint confirm (docs/09 §9.4): the gateway presents a certificate
+    // this device doesn't trust (self-signed). The user verifies the
+    // fingerprint on the gateway host, then confirms — the pin is stored in
+    // secure storage and the connect is retried, like an SSH host key.
+    if (pendingFingerprint != null) {
+        AlertDialog(
+            onDismissRequest = { pendingFingerprint = null },
+            title = { Text("Confirm gateway certificate") },
+            text = {
+                Column {
+                    Text(
+                        "The gateway presents a certificate this device doesn't trust. " +
+                            "Verify the fingerprint on the gateway host, then confirm to pin it.",
+                        style = MaterialTheme.typography.bodyMedium,
+                    )
+                    Spacer(modifier = Modifier.height(12.dp))
+                    Text(
+                        pendingFingerprint!!,
+                        style = MaterialTheme.typography.bodyMedium,
+                        fontFamily = FontFamily.Monospace,
+                    )
+                }
+            },
+            confirmButton = {
+                Button(
+                    onClick = {
+                        val fp = pendingFingerprint!!
+                        pendingFingerprint = null
+                        controller.confirmTlsFingerprint(fp)
+                        doConnect()
+                    },
+                ) { Text("Confirm & pin") }
+            },
+            dismissButton = {
+                TextButton(onClick = { pendingFingerprint = null }) { Text("Cancel") }
+            },
+        )
+    }
 }
@@ -0,0 +1,163 @@
+package iris.net
+
+import com.sun.net.httpserver.HttpsConfigurator
+import com.sun.net.httpserver.HttpsServer
+import okhttp3.OkHttpClient
+import okhttp3.Request
+import java.io.ByteArrayInputStream
+import java.net.InetSocketAddress
+import java.security.KeyFactory
+import java.security.KeyStore
+import java.security.cert.CertificateFactory
+import java.security.spec.PKCS8EncodedKeySpec
+import java.util.Base64
+import javax.net.ssl.KeyManagerFactory
+import javax.net.ssl.SSLContext
+import kotlin.test.Test
+import kotlin.test.assertEquals
+import kotlin.test.assertFailsWith
+import kotlin.test.assertNotNull
+
+/**
+ * docs/09 §9.4: end-to-end test of the fingerprint-confirm flow over a real
+ * TLS handshake: a local HTTPS server presents the embedded self-signed
+ * certificate (SAN: 127.0.0.1) to an OkHttp client wired exactly like
+ * [GatewayClient] (pinning socket factory + trust manager).
+ *
+ * 1. Unpinned: the handshake fails and [tlsFingerprintRequired] unwraps the
+ *    presented fingerprint from the nested exception.
+ * 2. After "confirming" (setting the pin): the SAME client connects — the
+ *    pin is read live, no client rebuild.
+ *
+ * The embedded key is a throwaway test key, not a secret.
+ */
+class TlsPinningIntegrationTest {
+    private companion object {
+        // Self-signed with SAN DNS:localhost, IP:127.0.0.1 (OkHttp's hostname
+        // verifier requires a SAN; CN-only certs are rejected even when pinned).
+        val CERT_PEM =
+            """
+            -----BEGIN CERTIFICATE-----
+            MIIC+zCCAeOgAwIBAgIUGXu+y1gH9kUWHAFlHOzrN3h2TRQwDQYJKoZIhvcNAQEL
+            BQAwGDEWMBQGA1UEAwwNaXJpcy1pbnQtdGVzdDAeFw0yNjA4MjQxOTE1MTJaFw0z
+            NjA4MjExOTE1MTJaMBgxFjAUBgNVBAMMDWlyaXMtaW50LXRlc3QwggEiMA0GCSqG
+            SIb3DQEBAQUAA4IBDwAwggEKAoIBAQCtqNGuSQm7iO2GuQ+TemTZsThzPVkWrfdF
+            /R25eCHTVSHfpXnlI2gXgRf5sBMLLOKVD/eTynelf2zcfuJqwYjCc6aOv1I9Fz2C
+            Eb+GBeyLHwmh4hSrMeN3YnoeaCmZzvbqNCpjEEmmw13Heptg6ZBcwISpE+78WVFT
+            qIeMGJ7/5X9cvoVebrQ6eV0LVGmzz5iqMp9uwoPeHnT7bGN3YXO9TSbjogSQbzRs
+            PS/JcZIFIUsfbOYRbNogd3v9SfKCfz9Q2J7EB8sBx8eCqXn5Q9avxk/VVYxjQL9a
+            GqxRCp4uCgQZt3GACZYvGzbMRFGNFlvhoYf20jE7Hly7OrYzJ4v7AgMBAAGjPTA7
+            MBoGA1UdEQQTMBGCCWxvY2FsaG9zdIcEfwAAATAdBgNVHQ4EFgQUA9qqz6IWojYd
+            WSbngx8h5vq9CTYwDQYJKoZIhvcNAQELBQADggEBAGNIGSCEy1A42UNUd+xREsHm
+            EmBJ7TYzxJjmweByJwdK5GjxmpaOXgcBjUb8O0Fzm8+4P2DDr/CXhv+aNYUcSCJ3
+            Xf5cBIXzJmTVvkLzdNpCmB9w2d66J2ZQYxCOZ4pUzvcXI6gK7qkrB2HALq2LYGtE
+            dxVocLizu+FGtf4ve+CuCZs3/tJaQPZYzP4UqV1oVfkg3hV+Yg1oFYFfrAelsFkw
+            zNjVh2jTwFiEpK5E/4OJtQaThOUkbkNcSc50ATYkPau9mA1IUTsOU/UNjMTbYtG0
+            Ht5KgYObXkwm44X0rgiGHgW61wqgIEa5ogfVIeCJzHwHNcn2J9yYlgYsZ/o8vrU=
+            -----END CERTIFICATE-----
+            """.trimIndent()
+
+        val KEY_PEM =
+            """
+            -----BEGIN PRIVATE KEY-----
+            MIIEvQIBADANBgkqhkiG9w0BAQEFAASCBKcwggSjAgEAAoIBAQCtqNGuSQm7iO2G
+            uQ+TemTZsThzPVkWrfdF/R25eCHTVSHfpXnlI2gXgRf5sBMLLOKVD/eTynelf2zc
+            fuJqwYjCc6aOv1I9Fz2CEb+GBeyLHwmh4hSrMeN3YnoeaCmZzvbqNCpjEEmmw13H
+            eptg6ZBcwISpE+78WVFTqIeMGJ7/5X9cvoVebrQ6eV0LVGmzz5iqMp9uwoPeHnT7
+            bGN3YXO9TSbjogSQbzRsPS/JcZIFIUsfbOYRbNogd3v9SfKCfz9Q2J7EB8sBx8eC
+            qXn5Q9avxk/VVYxjQL9aGqxRCp4uCgQZt3GACZYvGzbMRFGNFlvhoYf20jE7Hly7
+            OrYzJ4v7AgMBAAECggEABKYo2uQcrRcY2Mr6hkW4DnXmn3ssd+V3YbnJgm4bZbd5
+            PS4GaeJ9RmfP1wDmOZ3dgQUY6S1574XOScbh097ThPUop9iqYHVPUbyc5n8hGoZd
+            sSZGzGB9CPSrdUXvmy0FwjZcTiOg/SRszcrT/w+xrDIBOy+L7diMS1OPMWp1Uz9r
+            yHHxpjMtALToaMUHMNCRjyFRR0fgqGWnfwRVAwdKMxMQJZ0IiUXyuqgpdIBHZC+g
+            WIcntUDCiglHtuI34eoQQVVMhEm2ylaAq2tBaR7z3wGtXbbfdyWUi/DIkhS5o4HN
+            ux7AYF87WU87/0I8GpEQHdAFQKoqVgR8uaZmJ613YQKBgQDmcGZdYg4UtcjTVSDE
+            BHsLnFzapSjDebVsR2XWoztcvQIduqsh+2zV8RN3UGIOd7l9tEGWMm7rFFVOOs/f
+            utCAd4v5ZWtSs/KtSuL6PqbFuvD9jGVPaqsSAe/2WmAtG8vA/JIndFDC5CNo/Hem
+            Tj7XGAmEPKgTRLR9NY1fu0we2wKBgQDA7BemZXViw4RiEjUcsqX8yuFPGKlMyoCK
+            ieHsIO05dLD+s6BD7r8ang0twttwhCM4RoumxjEbEbRYMhu0EJKiC+wl53EM1Vcu
+            OBQAlgKMVGXKmp0K/moYOIdvb4JuHoITaYhKPyO+2/2rKLK3h+swnYJDrpOcOK7H
+            yqy1qeMBYQKBgQDRt+GxgxfFiVtn2cWkH1/MRVXMNxtOK2oNTT1FhfD0iZ9vZv9w
+            Qd3fJzPMFn/nItbRrEc0ZlnD4BFyzNt6hg5TnHjrVH3EGrj1NX40uOgWc/f3CNr6
+            190w2kqFLeLxqqZY0IRDG/yUIgSH+5z44aUXJG0kx/8+6fxJJ3+ubErumQKBgAZF
+            JhegYIpPNHRDhzphjAeFSIFbmdUHF9po1NDp2QvvAPmmOOU8UzW4QVFlbeBgSwy/
+            LjbDZkEs+CGNr1zQ1RMzM/+fYAs8u9Kiu/Ow7HBHJe/JyqTa0/Ppkm1KwIB3uV6M
+            JYPUPYMsfzga4IQahMhVtjAg8mc3aGbR7X8SAHDBAoGAOXIpfZ+mLejIlw4xUXQI
+            MMcw57cTWPQgU6w+YHt0njY4c5GcMKBxrbBMLFv0oeBj/2ZzBxw5TSWdXpA/4j3z
+            OBPuigr2mnlhJR8ahq1s0BSHhQbw7TIbazALi2cZ8Mdf7/hEIzuyY4efnyV7W+RO
+            sZ1EltfJHT57a0ub22mRtVc=
+            -----END PRIVATE KEY-----
+            """.trimIndent()
+
+        // `openssl x509 -noout -fingerprint -sha256` over CERT_PEM.
+        const val EXPECTED_FINGERPRINT =
+            "9B:25:54:2F:55:1B:20:32:34:B9:CF:E2:BB:DE:B3:E4:74:01:BF:FE:0F:5C:39:56:BE:F7:5E:E7:72:70:EB:44"
+
+        fun pemBody(pem: String): ByteArray {
+            val base64 = pem.replace(Regex("-----[A-Z ]+-----"), "").replace(" ", "").replace("\n", "")
+            return Base64.getDecoder().decode(base64)
+        }
+    }
+
+    @Test
+    fun selfSignedGatewayRequiresConfirmThenPins() {
+        val cert =
+            CertificateFactory
+                .getInstance("X.509")
+                .generateCertificate(ByteArrayInputStream(CERT_PEM.toByteArray()))
+                .let { it as java.security.cert.X509Certificate }
+        val key =
+            KeyFactory
+                .getInstance("RSA")
+                .generatePrivate(PKCS8EncodedKeySpec(pemBody(KEY_PEM)))
+
+        // Local HTTPS server presenting the self-signed cert.
+        val ks = KeyStore.getInstance(KeyStore.getDefaultType())
+        ks.load(null, null)
+        ks.setKeyEntry("iris", key, CharArray(0), arrayOf(cert))
+        val kmf = KeyManagerFactory.getInstance(KeyManagerFactory.getDefaultAlgorithm())
+        kmf.init(ks, CharArray(0))
+        val serverCtx = SSLContext.getInstance("TLS")
+        serverCtx.init(kmf.keyManagers, null, null)
+
+        val server = HttpsServer.create(InetSocketAddress("127.0.0.1", 0), 0)
+        server.httpsConfigurator = HttpsConfigurator(serverCtx)
+        server.createContext("/v1/health") { exchange ->
+            val body = "ok".toByteArray()
+            exchange.sendResponseHeaders(200, body.size.toLong())
+            exchange.responseBody.use { it.write(body) }
+        }
+        server.start()
+
+        // The client is wired exactly like GatewayClient: pinning socket
+        // factory + trust manager, pin read live from a mutable holder.
+        var pin = ""
+        val tm = PinningTrustManager { pin }
+        val client = OkHttpClient.Builder().sslSocketFactory(pinningSslSocketFactory(tm), tm).build()
+        val request = Request.Builder().url("https://127.0.0.1:${server.address.port}/v1/health").build()
+
+        try {
+            // 1. Unpinned: the handshake fails; the unwrap finds the
+            //    presented fingerprint in the nested exception chain.
+            val e =
+                assertFailsWith<Exception> {
+                    client.newCall(request).execute().use { it.body!!.string() }
+                }
+            val tls = tlsFingerprintRequired(e)
+            assertNotNull(tls, "expected TlsFingerprintRequired nested in: $e")
+            assertEquals(EXPECTED_FINGERPRINT, tls.fingerprint)
+
+            // 2. User "confirms" the fingerprint: the SAME client now
+            //    connects (the pin is read live, no client rebuild).
+            pin = EXPECTED_FINGERPRINT
+            client.newCall(request).execute().use { response ->
+                assertEquals(200, response.code)
+                assertEquals("ok", response.body!!.string())
+            }
+        } finally {
+            server.stop(0)
+            client.dispatcher.executorService.shutdown()
+            client.connectionPool.evictAll()
+        }
+    }
+}
@@ -0,0 +1,129 @@
+package iris.net
+
+import java.io.ByteArrayInputStream
+import java.io.IOException
+import java.security.cert.CertificateFactory
+import java.security.cert.X509Certificate
+import kotlin.test.Test
+import kotlin.test.assertEquals
+import kotlin.test.assertFailsWith
+import kotlin.test.assertNotNull
+import kotlin.test.assertNull
+import kotlin.test.assertTrue
+
+/**
+ * docs/09 §9.4: unit tests for the TLS fingerprint-confirm flow.
+ *
+ * The embedded certificate is a self-signed cert (CN=iris-test-gateway) the
+ * platform trust store does NOT contain, so it exercises the exact path a
+ * self-signed gateway hits: default trust manager rejects → the pinning
+ * manager either offers the fingerprint for confirmation or accepts the
+ * user-confirmed pin.
+ */
+class TlsPinningTest {
+    private companion object {
+        // Self-signed, 10-year validity — generated with:
+        //   openssl req -x509 -newkey rsa:2048 -nodes -subj "/CN=iris-test-gateway"
+        val SELF_SIGNED_PEM =
+            """
+            -----BEGIN CERTIFICATE-----
+            MIIDGTCCAgGgAwIBAgIUTNKIelZvTA7iFA+jx819cazOkE0wDQYJKoZIhvcNAQEL
+            BQAwHDEaMBgGA1UEAwwRaXJpcy10ZXN0LWdhdGV3YXkwHhcNMjYwODI0MTkxMDA3
+            WhcNMzYwODIxMTkxMDA3WjAcMRowGAYDVQQDDBFpcmlzLXRlc3QtZ2F0ZXdheTCC
+            ASIwDQYJKoZIhvcNAQEBBQADggEPADCCAQoCggEBANZ2zK/jRQFB+dHSCfXVm9pp
+            9+scyP3CjQr7Ec6b/aNfBKGoOXM5m8fvmYjJefeWgBLpr8I+g0BIn2+BNK80Tp3V
+            LlHiu3DQMmPfd7XTVQhmq19pjEYYsCcZ8QnPZ/WwMSRaQar0NKK6TS2MOHA8VdEs
+            BjeQoiTczO+HXlzXf20nhEtnWfNc3RBM0y6GIu+eKKKb9Hiri6LdpecQ9pGdxLXc
+            HZP6SjM5FH/prqoVPGV+Q1wCh6K0iwUjCGrsO0QDFvoe4W2eLG1QW6LEpNj7ym66
+            UmVG3aB9q3zpZ4Cc3kHVV43QqSgp+t5BtBLIWM0bnZ2IPbdSexpI22+AANliY3UC
+            AwEAAaNTMFEwHQYDVR0OBBYEFKUZIe8CbNWYSNkZBMRKRIYpGErJMB8GA1UdIwQY
+            MBaAFKUZIe8CbNWYSNkZBMRKRIYpGErJMA8GA1UdEwEB/wQFMAMBAf8wDQYJKoZI
+            hvcNAQELBQADggEBACJLF9A7OKWQU3wBWw00ezf6zdQcZHJvGcBTr0WSDg5/QNsj
+            GD8Dz8Feu1zCVEKXAxB3NaiO7IS/S/kR8Oo0SVs55JEfW5BHGs5Mdt74/Ch8khy/
+            Wvvj2BZakmqyW5LZkxlIPEoyhhyoCSBGQIpmCDQXKAlSrUZj9gaAn4uaBOVBIu4S
+            vIQZTtouhc1rX+Ov0HgwBCBbDPL2pBjkUUKqUrD249eyL2+qTWLAf6J56x6UYFAA
+            I2Eg5W3bTqLYz8CbnmKrR7KhfTAmkgCY1HIQpWoIVAsXRmaebzPsYeGK5gf6tnP2
+            vn2/tqbereUqqCMRr0wBZjaJzPnu46N43yOGrEs=
+            -----END CERTIFICATE-----
+            """.trimIndent()
+
+        // `openssl x509 -noout -fingerprint -sha256` over the same cert.
+        const val EXPECTED_FINGERPRINT =
+            "C8:16:8E:7A:7F:9D:6E:20:07:6F:85:50:F7:B3:E4:B4:9C:DB:70:CA:D8:18:1B:4B:50:FA:5D:FC:4A:62:8C:FA"
+
+        val CERT: X509Certificate by lazy {
+            CertificateFactory
+                .getInstance("X.509")
+                .generateCertificate(ByteArrayInputStream(SELF_SIGNED_PEM.toByteArray()))
+                .let { it as X509Certificate }
+        }
+    }
+
+    @Test
+    fun certFingerprintMatchesOpenSsl() {
+        assertEquals(EXPECTED_FINGERPRINT, certFingerprint(CERT))
+    }
+
+    @Test
+    fun unpinnedSelfSignedCertOffersFingerprintForConfirmation() {
+        val tm = PinningTrustManager { "" }
+        val e =
+            assertFailsWith<TlsFingerprintRequired> {
+                tm.checkServerTrusted(arrayOf(CERT), "RSA")
+            }
+        assertEquals(EXPECTED_FINGERPRINT, e.fingerprint)
+    }
+
+    @Test
+    fun confirmedPinAcceptsTheSelfSignedCert() {
+        val tm = PinningTrustManager { EXPECTED_FINGERPRINT }
+        // Must not throw: the user confirmed exactly this certificate.
+        tm.checkServerTrusted(arrayOf(CERT), "RSA")
+    }
+
+    @Test
+    fun wrongPinStillFailsWithThePresentedFingerprint() {
+        val tm = PinningTrustManager { "DE:AD:BE:EF" }
+        val e =
+            assertFailsWith<TlsFingerprintRequired> {
+                tm.checkServerTrusted(arrayOf(CERT), "RSA")
+            }
+        assertEquals(EXPECTED_FINGERPRINT, e.fingerprint)
+    }
+
+    @Test
+    fun pinIsReadLive() {
+        // The provider is a lambda: a pin saved AFTER the manager was built
+        // (the confirm dialog's action) takes effect without rebuilding it.
+        var pin = ""
+        val tm = PinningTrustManager { pin }
+        assertFailsWith<TlsFingerprintRequired> {
+            tm.checkServerTrusted(arrayOf(CERT), "RSA")
+        }
+        pin = EXPECTED_FINGERPRINT
+        tm.checkServerTrusted(arrayOf(CERT), "RSA")
+    }
+
+    @Test
+    fun unwrapFindsNestedTlsFingerprintRequired() {
+        val inner = TlsFingerprintRequired(EXPECTED_FINGERPRINT)
+        // The JSSE/OkHttp layers wrap the trust manager's exception in an
+        // (SSL) handshake IOException — the unwrap must find it nested.
+        val wrapped = IOException("PKIX path building failed", inner)
+        val found = tlsFingerprintRequired(wrapped)
+        assertNotNull(found)
+        assertEquals(EXPECTED_FINGERPRINT, found.fingerprint)
+        // Unrelated failures must not be misread as a confirm request.
+        assertNull(tlsFingerprintRequired(IOException("remote host closed connection")))
+        assertNull(tlsFingerprintRequired(IllegalStateException("gateway unreachable")))
+    }
+
+    @Test
+    fun pinningSocketFactoryCreatesSockets() {
+        val tm = PinningTrustManager { "" }
+        val factory = pinningSslSocketFactory(tm)
+        val socket = factory.createSocket()
+        assertTrue(socket.javaClass.name.contains("SSL"))
+        socket.close()
+    }
+}
@@ -73,6 +73,7 @@ class DesktopSecureStore : SecureStore {
        val fontSizeScale: Float = 1.0f,
        val runtimeFooterEnabled: Boolean = false,
        val runtimeFooterFields: String = "",
+        val pinnedCertFingerprint: String = "",
    )

    init {
@@ -284,6 +285,13 @@ class DesktopSecureStore : SecureStore {
            save(d.copy(runtimeFooterFields = value))
        }

+    override var pinnedCertFingerprint: String
+        get() = load().pinnedCertFingerprint
+        set(value) {
+            val d = load()
+            save(d.copy(pinnedCertFingerprint = value.trim()))
+        }
+
    override fun savePairing(
        url: String,
        token: String,
@@ -311,6 +319,7 @@ class DesktopSecureStore : SecureStore {
                ntfyTopic = "",
                ntfyServer = "",
                pushBackend = "",
+                pinnedCertFingerprint = "",
            ),
        )
        secret.clear()