Merge branch 'app-embeds-ca-from-config'

The app pins the CA of the machine that builds it, read at build time
rather than pasted into the source; state and certificates move out of the
shared repo; certificates are generated in process; and the sibling
project's rename to dev-updater is followed here.

AGENTS.md

@@ -22,11 +22,11 @@ session-type branch in shared code (routes, transcript, app screens).
 
 ## Layout
 
-Mirrors `../local-updater` deliberately — same stack (axum 0.8 +
+Mirrors `../dev-updater` deliberately — same stack (axum 0.8 +
 axum-server/rustls, tokio, clap; Kotlin 2.4.x + Compose Multiplatform,
 single `:androidApp` module), same cert scheme, same registry pattern (every
 session mutation funnels through the manager so in-memory and on-disk state
-can't come apart). Read local-updater's `README.md` and `AGENTS.md` for the
+can't come apart). Read dev-updater's `README.md` and `AGENTS.md` for the
 conventions before diverging from them; module-by-module intent for this
 repo is in PLAN.md's "Backend layout" section.
 
@@ -40,10 +40,11 @@ repo is in PLAN.md's "Backend layout" section.
   `when`; `Api.kt`/`EventStream.kt` the REST + SSE clients; `Events.kt` the
   event model mirror; `ServerConfig.kt` settings + Keystore-sealed token;
   screens in `SessionListScreen/SessionScreen/SpawnScreen/SettingsScreen`.
-- `gen-dev-cert.sh` / `certs/` — copied from local-updater's scheme
-  (idempotent CA, reissued leaf; regenerating the CA strands the installed
-  app — same one-way door). Dev SANs cover 127.0.0.1, 10.0.2.2 (emulator →
-  host), and the LAN IP alongside the WireGuard address.
+- `server/src/certs.rs` — the TLS certificates, generated in process on
+  first start into `$XDG_CONFIG_HOME/ai-app/certs`: idempotent CA, leaf
+  reissued every start covering every local IPv4 plus 127.0.0.1 and
+  10.0.2.2 (emulator → host). Regenerating the CA strands the installed
+  app — the one-way door.
 
 ## Status
 
@@ -59,8 +60,15 @@ real-phone/WireGuard bring-up, which is operational rather than code.
 
 - Server: `./run-tests.sh` (or `cargo test`) + `cargo clippy --all-targets`
   from `server/` — the build stays warning-clean, keep it that way.
-- App: from `app/`, `. ./android-env.sh && ./gradlew :androidApp:compileDebugKotlin`;
-  `./run-android.sh` builds, installs, and launches on the emulator.
+- App: from `app/`, `. ./android-env.sh && ./gradlew :androidApp:compileDebugKotlin`
+  to typecheck; `./build-apk.sh` to produce the APK to install on a phone
+  (through Dev Updater); `./run-android.sh` to build, install, and launch
+  on the emulator.
+- **The APK pins the CA of the machine that builds it**, read at build time
+  from `$XDG_CONFIG_HOME/ai-app/certs/ca.pem` (`AI_APP_CA` overrides) and
+  generated into a constant. So the server must have started once on that
+  machine first — the build stops with that instruction otherwise — and an
+  APK built in this VM only works against a server in this VM.
 - Run the server for development with `--bind 127.0.0.1` (wg0 doesn't exist
   on this machine yet; the default fails closed). First run prints the
   enrollment QR/URI with the token — capture it from the log.
@@ -75,7 +83,7 @@ real-phone/WireGuard bring-up, which is operational rather than code.
 Established 2026-08-25, and it decides more than it looks like:
 
 - **The host (192.168.1.168) is the backend machine.** It runs
-  local-updater's server today and is where `ai-server` belongs in
+  dev-updater's server today and is where `ai-server` belongs in
   production: it has the LAN address the phone can reach, and it's where
   WireGuard terminates. `wg-setup-host.sh` sets that up (keys, `wg0.conf`,
   the phone's QR); run it there with `sudo WG_ENDPOINT=<ddns name>`.
@@ -115,9 +123,11 @@ Established 2026-08-25, and it decides more than it looks like:
   PLAN.md's security section), and the repo is shared read-write with the
   host, so state lives outside it: `$XDG_CONFIG_HOME/ai-app/config.json`
   and `certs/`, `$XDG_DATA_HOME/ai-app/sessions/`, owner-only.
-- Certificates are generated **on the machine that serves them**
-  (`./gen-dev-cert.sh`, honours `AI_APP_CERTS`). Running it in the VM makes
-  a separate throwaway dev CA for emulator work — never install a build
+- Certificates are generated **by the server, on first start**, into
+  `$XDG_CONFIG_HOME/ai-app/certs` (`--certs` overrides). The CA is created
+  once and then left alone; the leaf is reissued every start, so covering a
+  new address is a restart. Starting the server in the VM therefore makes a
+  separate throwaway dev CA for emulator work — never install a build
   pinning that on the real phone.
 - Point development at a scratch state directory rather than the real one:
   `--config /tmp/…/config.json --data-dir /tmp/…/sessions --port 8444`, or
@@ -138,11 +148,19 @@ Established 2026-08-25, and it decides more than it looks like:
 - **CMP 1.11 deprecates the `compose.*` dependency accessors** — declare
   `org.jetbrains.compose.<x>:<x>` directly (material3 has its own release
   train, separate from the CMP version).
+- **A PEM constant must start at the opening quotes.** A generated
+  `"""\n-----BEGIN CERTIFICATE-----` costs Android's `CertificateFactory`
+  its preamble sniff, so it tries DER instead and fails at runtime with
+  `ASN.1 ... DECODE_ERROR` — nowhere near the code that produced it.
+- **AGP 9 refuses `Provider`s in the source-set API**: generated sources go
+  through `androidComponents.onVariants { it.sources.java?.addGenerated
+  SourceDirectory(task, Task::outputDir) }`, which also carries the task
+  dependency.
 
-## Environment notes (this machine, learned in local-updater)
+## Environment notes (this machine, learned in dev-updater)
 
 - Android SDK is at `~/Android/Sdk`, not the root-owned `/opt/android-sdk`
-  the ambient `$ANDROID_HOME` may point at; copy local-updater's
+  the ambient `$ANDROID_HOME` may point at; copy dev-updater's
   `android-env.sh` override pattern.
 - Each agent command runs in a fresh shell — exported environment does not
   carry over. Chain: `cd app && . ./android-env.sh && ./gradlew …`. Never
@@ -153,5 +171,5 @@ Established 2026-08-25, and it decides more than it looks like:
   (`setsid nohup … & disown -h`, verify `PPID 1`), and every
   `pgrep -f`/`pkill -f` pattern needs its first character bracketed
   (`[a]i-server`) in **every** occurrence in the command, or the pattern
-  matches the shell running it. Full explanation in local-updater's
+  matches the shell running it. Full explanation in dev-updater's
   `AGENTS.md` — it bites exactly the same way here.

PLAN.md

@@ -7,7 +7,7 @@ the official app gets wrong (e.g. it won't deliver a typed message until the
 session fully finishes its turn, where the TUI injects it at the next tool
 boundary).
 
-Same shape as `../local-updater`: a Rust (Axum) backend on the desktop, a
+Same shape as `../dev-updater`: a Rust (Axum) backend on the desktop, a
 Kotlin/Compose Android app, pinned self-signed TLS between them.
 
 ## The one idea everything hangs off
@@ -81,12 +81,12 @@ backend (Rust/Axum, desktop)
 
 ### Backend layout (`server/`)
 
-Mirroring local-updater's stack: axum 0.8, axum-server + rustls, tokio, serde,
+Mirroring dev-updater's stack: axum 0.8, axum-server + rustls, tokio, serde,
 clap, tracing. Rust edition 2024, warning-clean, clippy in CI habit.
 
 - `main.rs` — bootstrap, TLS listener.
 - `routes.rs` — the whole HTTP table in one module doc comment (as in
-  local-updater).
+  dev-updater).
 - `session/mod.rs` — `SessionManager`: the live session registry, every
   mutation funnels through it (the `registry.rs` pattern: in-memory and
   on-disk state can't come apart).
@@ -259,9 +259,24 @@ complete path out of everything spawning one created.
 
 ### Security
 
-- TLS with a self-signed CA, pinned in the app — `gen-dev-cert.sh` and
-  `PinnedCert.kt` copied from local-updater, same idempotent-CA/reissued-leaf
-  scheme, same one-way-door caveat about regenerating the CA.
+- TLS with a self-signed CA, pinned in the app — same
+  idempotent-CA/reissued-leaf scheme as dev-updater, same one-way-door
+  caveat about regenerating the CA, but generated **in process on first
+  start** (`certs.rs`) rather than by a shell script calling openssl
+  (2026-08-25). One place then decides the extensions, the file modes, and
+  which addresses the leaf covers — every local IPv4 plus loopback and the
+  emulator's host alias, so nobody maintains a hardcoded IP — and there is
+  no setup step to forget.
+  - Unlike dev-updater, the pinned CA is **not a constant in the source**:
+    the build reads `$XDG_CONFIG_HOME/ai-app/certs/ca.pem` from the machine
+    doing the build and generates the constant (`generatePinnedCert` in
+    `app/androidApp/build.gradle.kts`; `AI_APP_CA` overrides). Decided
+    2026-08-25, and it does three things at once — the trust anchor follows
+    the build machine, so an APK built on the backend host pins that host
+    and one built in the dev VM pins the VM's throwaway CA and is only good
+    for its emulator; there is no second anchor to add for development and
+    forget to remove; and regenerating a CA needs a rebuild rather than a
+    paste, so a stale constant can't quietly disagree with the server.
 - **The dev VM is untrusted** (decided 2026-08-25): a machine that isn't
   malicious but could become so. It matters because the repo is a
   read-write virtiofs mount shared between the VM and the backend host, so
@@ -377,12 +392,12 @@ complete path out of everything spawning one created.
     a deliberate flag, never a fallback, so the fail-closed default is
     untouched (2026-08-24).
 - The bootstrap-over-HTTP trick from the updater is unnecessary here — the
-  app installs via Local Updater.
+  app installs via Dev Updater.
 
 ## App (`app/`)
 
 Kotlin + Compose Multiplatform, single `:androidApp` module, same versions as
-local-updater (Kotlin 2.4.x, CMP 1.11.x, JDK 21). Screens:
+dev-updater (Kotlin 2.4.x, CMP 1.11.x, JDK 21). Screens:
 
 1. **Session list** — cards: kind icon, title, host, model, status
    (running / awaiting answer / idle / exited), last activity. Spawn FAB;
@@ -405,7 +420,7 @@ local-updater (Kotlin 2.4.x, CMP 1.11.x, JDK 21). Screens:
 5. **Settings** — server address + token, hosts editor, llama model list
    editor.
 
-Networking mirrors local-updater's app layer (`AppsApi.kt` style thin client +
+Networking mirrors dev-updater's app layer (`AppsApi.kt` style thin client +
 pinned transport), plus an SSE client with `after=` resume driven by
 connectivity/lifecycle. The app keeps no persistent transcript store — the
 backend's transcript is the source of truth; the app caches only for the
@@ -486,7 +501,7 @@ window just fills.
 Each phase ends runnable and verified against the real thing (rule 22); the
 backend gets tests where logic is pure (event normalization, transcript
 cursors, config persistence, refcounting) — the app is UI over the API and is
-verified by running it, matching local-updater's posture.
+verified by running it, matching dev-updater's posture.
 
 ## Open questions / risks
 
@@ -524,6 +539,6 @@ installed versions when each phase starts):
   ≥180 s polling; wrong User-Agent → aggressive 429 bucket):
   https://github.com/anthropics/claude-code/issues/31637 and
   https://github.com/Maciek-roboblog/Claude-Code-Usage-Monitor/issues/202
-- Sibling project this repo's conventions mirror: `../local-updater`
+- Sibling project this repo's conventions mirror: `../dev-updater`
   (README.md + AGENTS.md — server/registry/routes layout, cert scheme,
   testing posture, Android env notes).

app/androidApp/build.gradle.kts

@@ -4,6 +4,84 @@ plugins {
     alias(libs.plugins.composeCompiler)
 }
 
+// The CA this app pins is baked in at build time from the certificates on
+// the machine doing the build -- `$XDG_CONFIG_HOME/ai-app/certs/ca.pem`,
+// which the server generates on first start. AI_APP_CA overrides the path.
+//
+// Reading it rather than keeping a pasted copy in the source is what makes
+// the trust boundary follow the build: an APK built on the backend host
+// pins the host's CA and never sees any other, while one built in the dev
+// VM pins that VM's throwaway CA and is only good for its emulator. There
+// is no second trust anchor to get wrong, and no stale paste to notice
+// three days later. It also means the private key never has to exist
+// anywhere near this repo.
+val pinnedCaPath: String = System.getenv("AI_APP_CA")
+    ?: "${System.getenv("XDG_CONFIG_HOME") ?: "${System.getProperty("user.home")}/.config"}" +
+    "/ai-app/certs/ca.pem"
+
+abstract class GeneratePinnedCert : DefaultTask() {
+    /** Where the certificate is looked for, reported in failures. */
+    @get:Input
+    abstract val caPath: Property<String>
+
+    /**
+     * The certificate itself, set only when it exists -- so a missing one
+     * produces this task's own instructions rather than Gradle's "no such
+     * input file", which doesn't say what to run.
+     */
+    @get:InputFile
+    @get:Optional
+    @get:PathSensitive(PathSensitivity.NONE)
+    abstract val caCertificate: RegularFileProperty
+
+    /** Wired by AGP through `addGeneratedSourceDirectory`. */
+    @get:OutputDirectory
+    abstract val outputDir: DirectoryProperty
+
+    @TaskAction
+    fun generate() {
+        val path = caPath.get()
+        val ca = File(path)
+        if (!ca.isFile) {
+            throw GradleException(
+                "No CA certificate at $path.\n" +
+                    "Start ai-server once on this machine first -- it generates the CA the " +
+                    "app pins, and the certificate has to exist before an APK can embed it.\n" +
+                    "Set AI_APP_CA=/path/to/ca.pem to build against a different one.",
+            )
+        }
+        val pem = ca.readText().trim()
+        if (!pem.startsWith("-----BEGIN CERTIFICATE-----")) {
+            throw GradleException("$path is not a PEM certificate.")
+        }
+        val file = outputDir.get().file("PinnedCaCertificate.kt").asFile
+        file.parentFile.mkdirs()
+        // The PEM must start immediately after the opening quotes: a
+        // leading newline makes Android's CertificateFactory stop
+        // recognising the "-----BEGIN" preamble and try to parse the whole
+        // thing as DER, which fails with an ASN.1 decode error at runtime
+        // rather than anywhere near this file.
+        file.writeText(
+            """
+            |// Generated from $path by the generatePinnedCert task. Do not edit.
+            |package com.example.aiapp
+            |
+            |const val PINNED_CA_PEM = ""${'"'}$pem
+            |""${'"'}
+            |
+            """.trimMargin(),
+        )
+    }
+}
+
+val generatePinnedCert = tasks.register<GeneratePinnedCert>("generatePinnedCert") {
+    val ca = file(pinnedCaPath)
+    caPath.set(pinnedCaPath)
+    if (ca.isFile) {
+        caCertificate.set(ca)
+    }
+}
+
 android {
     namespace = "com.example.aiapp"
     compileSdk = 37
@@ -31,6 +109,17 @@ android {
     }
 }
 
+// AGP 9 wants generated sources registered through the variant API rather
+// than added to a source set, so the task dependency is carried properly.
+androidComponents {
+    onVariants { variant ->
+        variant.sources.java?.addGeneratedSourceDirectory(
+            generatePinnedCert,
+            GeneratePinnedCert::outputDir,
+        )
+    }
+}
+
 dependencies {
     implementation(libs.compose.runtime)
     implementation(libs.compose.foundation)

app/androidApp/src/main/AndroidManifest.xml

@@ -6,7 +6,7 @@
          network address, including a plain socket to a LAN IP literal.
          Without it the traffic is silently dropped, surfacing only as a
          connect timeout. See MainActivity.kt's runtime request, and
-         local-updater's manifest for the full story. -->
+         dev-updater's manifest for the full story. -->
     <uses-permission android:name="android.permission.ACCESS_LOCAL_NETWORK" />
 
     <application

app/androidApp/src/main/kotlin/com/example/aiapp/MainActivity.kt

@@ -36,7 +36,7 @@ class MainActivity : ComponentActivity() {
 
         // Transparent status bar on every version; the Surface below paints
         // through underneath it and content insets itself. Same reasoning
-        // as local-updater's MainActivity.
+        // as dev-updater's MainActivity.
         enableEdgeToEdge()
         WindowCompat.getInsetsController(window, window.decorView).isAppearanceLightStatusBars = true
 

app/androidApp/src/main/kotlin/com/example/aiapp/PinnedCert.kt

@@ -10,31 +10,19 @@ import javax.net.ssl.SSLSocketFactory
 import javax.net.ssl.TrustManagerFactory
 import javax.net.ssl.X509TrustManager
 
-/**
- * PEM-encoded dev CA certificate this repo's `gen-dev-cert.sh` generates --
- * the sole trust anchor for every request this app makes. The server's TLS
- * listener presents a leaf certificate signed by this CA. Everything behind
- * that listener *is* remote code execution on the backend, so this app
- * trusts exactly this CA and nothing else -- not even the system store.
- *
- * Regenerating that CA means updating this to match; its SHA-256
- * fingerprint is printed by the script and saved to `certs/ca-sha256.txt`.
- * The QR enrollment deliberately does not carry the CA: trust lives here in
- * the APK, so photographing the terminal leaks only the (rotatable) token.
- */
-const val PINNED_CA_PEM = """-----BEGIN CERTIFICATE-----
-MIIBvzCCAWWgAwIBAgIUGCxNZPJIfzGQipZGxWVZ8vMYZXgwCgYIKoZIzj0EAwIw
-LTETMBEGA1UECgwKYWktYXBwIGRldjEWMBQGA1UEAwwNYWktYXBwIGRldiBDQTAe
-Fw0yNjA4MjUwMTI2MDRaFw0zNjA4MjIwMTI2MDRaMC0xEzARBgNVBAoMCmFpLWFw
-cCBkZXYxFjAUBgNVBAMMDWFpLWFwcCBkZXYgQ0EwWTATBgcqhkjOPQIBBggqhkjO
-PQMBBwNCAARE6qRKz1HeCzcvmdT6ztwTR2w4DGP97aaYJhp3z+es6dceNXdpP1qx
-3DlazArgYLjOcNOHTqonj4H5NwHfeP4So2MwYTAdBgNVHQ4EFgQUL9VAISmEPDhJ
-dHnl5iS10qLbcekwHwYDVR0jBBgwFoAUL9VAISmEPDhJdHnl5iS10qLbcekwDwYD
-VR0TAQH/BAUwAwEB/zAOBgNVHQ8BAf8EBAMCAQYwCgYIKoZIzj0EAwIDSAAwRQIh
-AL7Z0wfT0pXD08J6GNbPVfy/PB3EoUtIwA9z9rYGPEhZAiBeLPiXCvIbWWTpsjRr
-Uk5VTHJchx0xXCdTRSJo2BEh7Q==
------END CERTIFICATE-----
-"""
+// PINNED_CA_PEM is generated at build time from the CA on the machine doing
+// the build -- see the generatePinnedCert task in build.gradle.kts. It is
+// deliberately not a checked-in constant: the private key that signs against
+// it must never be anywhere this repo is, and an APK should pin whatever CA
+// the backend it was built for actually serves.
+//
+// So the trust anchor follows the build machine. Built on the backend host,
+// the app trusts that host and nothing else -- not even the system store.
+// Built in the dev VM, it trusts that VM's throwaway CA and is good only for
+// its emulator; never install one of those on a real phone.
+//
+// The QR enrollment deliberately carries no CA: trust lives here in the APK,
+// so photographing the terminal leaks only the (rotatable) token.
 
 /**
  * Trusts only [PINNED_CA_PEM], not the device's system trust store, so a
@@ -43,8 +31,11 @@ Uk5VTHJchx0xXCdTRSJo2BEh7Q==
  * KeyStore/TrustManager setup from scratch.
  */
 val pinnedSslSocketFactory: SSLSocketFactory by lazy {
+    // Trimmed because CertificateFactory only recognises PEM when the
+    // "-----BEGIN" preamble is the very first thing it sees; surrounding
+    // whitespace sends it down the DER path instead.
     val caCert = CertificateFactory.getInstance("X.509")
-        .generateCertificate(ByteArrayInputStream(PINNED_CA_PEM.encodeToByteArray()))
+        .generateCertificate(ByteArrayInputStream(PINNED_CA_PEM.trim().encodeToByteArray()))
     val keyStore = KeyStore.getInstance(KeyStore.getDefaultType()).apply {
         load(null, null)
         setCertificateEntry("ai-app-dev-ca", caCert)

app/androidApp/src/main/kotlin/com/example/aiapp/SessionListScreen.kt

@@ -36,7 +36,7 @@ import kotlinx.coroutines.launch
 import kotlinx.coroutines.withContext
 
 // Status colors, keyed by the wire strings in Events.kt. Light theme only,
-// as in local-updater.
+// as in dev-updater.
 private val AWAITING_COLOR = Color(0xFFB26A00)
 private val RUNNING_COLOR = Color(0xFF2E7D32)
 

app/build-apk.sh

@@ -0,0 +1,69 @@
+#!/bin/sh
+# Builds the app's APK, ready to install on a phone through Dev Updater.
+#
+#   ./build-apk.sh
+#
+# The APK pins the CA on *this* machine ($XDG_CONFIG_HOME/ai-app/certs/ca.pem,
+# or AI_APP_CA), so build it on the machine that runs the backend: an app
+# built somewhere else trusts a CA that backend can't present, and simply
+# won't connect. Start ai-server once first if there are no certificates
+# yet -- it generates them; the build stops with that instruction if it
+# can't find one.
+#
+# Unlike ./run-android.sh, this touches no emulator: it only produces the
+# file. Installing on a real phone goes through Dev Updater, which serves
+# whatever is under this project's build directory.
+set -eu
+
+SCRIPT_DIR=$(cd "$(dirname "$0")" && pwd)
+cd "$SCRIPT_DIR"
+
+# Prefer an SDK this machine has already configured -- the host and the dev
+# VM don't keep it in the same place, and android-env.sh is written for the
+# VM's layout (it also installs missing packages, which isn't wanted here).
+if [ -n "${ANDROID_HOME:-}" ] && [ -d "${ANDROID_HOME}" ]; then
+    echo "==> Using ANDROID_HOME=$ANDROID_HOME"
+elif [ -n "${ANDROID_SDK_ROOT:-}" ] && [ -d "${ANDROID_SDK_ROOT}" ]; then
+    ANDROID_HOME="$ANDROID_SDK_ROOT"
+    export ANDROID_HOME
+    echo "==> Using ANDROID_SDK_ROOT=$ANDROID_SDK_ROOT"
+elif [ -d "$HOME/Android/Sdk" ]; then
+    ANDROID_HOME="$HOME/Android/Sdk"
+    ANDROID_SDK_ROOT="$ANDROID_HOME"
+    export ANDROID_HOME ANDROID_SDK_ROOT
+    echo "==> Using $ANDROID_HOME"
+else
+    echo "No Android SDK found. Set ANDROID_HOME to it, or install one" >&2
+    echo "(Android Studio's default location is ~/Android/Sdk)." >&2
+    exit 1
+fi
+
+CA="${AI_APP_CA:-${XDG_CONFIG_HOME:-$HOME/.config}/ai-app/certs/ca.pem}"
+if [ -f "$CA" ]; then
+    # Printed so a wrong or stale certificate is visible here rather than as
+    # a handshake failure on the phone. Compare with the server's own
+    # the CA the server is actually presenting.
+    FINGERPRINT=$(openssl x509 -in "$CA" -pubkey -noout 2>/dev/null \
+        | openssl pkey -pubin -outform der 2>/dev/null \
+        | openssl dgst -sha256 -binary 2>/dev/null \
+        | openssl base64 2>/dev/null || echo "(openssl unavailable)")
+    echo "==> Pinning the CA at $CA"
+    echo "    fingerprint: $FINGERPRINT"
+else
+    echo "No CA certificate at $CA -- start ai-server once on this machine" >&2
+    echo "(it generates them), or set AI_APP_CA. The APK embeds it at build time." >&2
+    exit 1
+fi
+
+echo "==> Building"
+./gradlew :androidApp:assembleDebug
+
+APK="$SCRIPT_DIR/androidApp/build/outputs/apk/debug/androidApp-debug.apk"
+echo
+echo "==> Built $APK"
+[ -f "$APK" ] && ls -lh "$APK" | awk '{print "    " $5}'
+echo
+echo "To get it onto the phone: add this project to Dev Updater (or hit"
+echo "Update on it if it's already there) and install from there."
+echo "Then start the backend and scan the enrollment QR it prints:"
+echo "    ./server/target/release/ai-server --rotate-token"

app/run-android.sh

@@ -1,6 +1,6 @@
 #!/bin/sh
 # Builds and runs this app on an emulator, creating/booting the AVD first if
-# it isn't already up. Same flow as local-updater's run-android.sh; see that
+# it isn't already up. Same flow as dev-updater's run-android.sh; see that
 # script for the reasoning behind the avd handling.
 #
 # Environment setup (SDK location, PATH, ...) lives in ./android-env.sh,

gen-dev-cert.sh

@@ -1,142 +0,0 @@
-#!/bin/sh
-# Generates the self-signed dev CA and leaf certificate `server/` serves its
-# TLS listener with. Run it once, ON THE MACHINE THAT RUNS THE BACKEND, before
-# the first start; the server exits with a clear message if the certificates
-# are missing.
-#
-# Same scheme as ../local-updater's: nothing on a device trusts this
-# automatically -- the app embeds the CA certificate verbatim and pins to it
-# (`PinnedCert.kt`), rather than relying on the device's system trust store.
-# This server's API *is* remote code execution (it spawns AI sessions on
-# request), so a MITM on it would be as bad as it gets -- hence pinning.
-#
-# WHERE THE KEYS LIVE, AND WHY NOT IN THE REPO
-#
-# Output goes to $XDG_CONFIG_HOME/ai-app/certs (0700), deliberately *not*
-# beside this script. The repo is a virtiofs mount shared with the dev VM,
-# and that VM is treated as untrusted -- a machine that isn't malicious but
-# could become so. A CA private key it can read is a CA private key it can
-# sign with, and a leaf signed by this CA is one the phone's pinned app
-# accepts without question. Keeping the key off the shared mount is what
-# makes pinning mean anything.
-#
-# The same reasoning says the CA key doesn't belong on the backend either,
-# strictly: the server only ever reads leaf.pem and leaf-key.pem, and the CA
-# key is needed solely to reissue a leaf. Moving ca-key.pem somewhere offline
-# once the setup is stable costs nothing but having it to hand at reissue.
-#
-# Running this inside the VM is fine and expected for emulator work -- it
-# just produces a *different*, throwaway CA there. Never install a build
-# pinning that dev CA on the real phone.
-#
-# The CA is idempotent -- skipped if `certs/ca.pem` already exists, so
-# re-running this doesn't invalidate the certificate the installed app has
-# pinned against without a reason to. The leaf is cheap and reissued on
-# every run (still signed by that same, unchanged CA), so adding another SAN
-# entry only means rerunning this script, not touching anything pinned.
-#
-# The leaf's SANs must cover every address a device reaches this server at.
-# In production that is exactly one: the backend's WireGuard address, which
-# the phone uses from everywhere (see PLAN.md's off-network section).
-# Override with SERVER_IP=... if your wg0 address differs.
-#
-# Outputs into `certs/` (gitignored -- private key material, and the whole
-# thing is trivially regeneratable anyway):
-#   ca.pem           the CA certificate (not its private key) -- what the
-#                     app embeds and pins against.
-#   ca-key.pem       the CA's private key -- only this script needs it, to
-#                     sign the leaf below. Never shipped anywhere.
-#   leaf.pem         the server's own certificate (CA-signed), presented on
-#                     every TLS handshake.
-#   leaf-key.pem     the leaf's private key -- what the server loads to
-#                     terminate TLS.
-#   ca-sha256.txt    the CA certificate's SPKI SHA-256 fingerprint, printed
-#                     below too. Informational -- the app embeds the whole
-#                     `ca.pem`, not this digest.
-#   leaf-sha256.txt  the leaf's SPKI SHA-256 fingerprint. Informational --
-#                     nothing pins the leaf; the app pins the CA and
-#                     validates the chain.
-
-set -eu
-
-SCRIPT_DIR=$(cd "$(dirname "$0")" && pwd)
-CERTS_DIR="${AI_APP_CERTS:-${XDG_CONFIG_HOME:-$HOME/.config}/ai-app/certs}"
-# The backend's WireGuard address -- the one address the phone ever dials in
-# production (PLAN.md: single-path addressing, no home/away distinction).
-SERVER_IP="${SERVER_IP:-10.66.0.1}"
-# Also covered so development before the tunnel exists can complete a real
-# handshake against the same pinned CA:
-#   127.0.0.1  curl from the machine itself, and tests binding loopback
-#   10.0.2.2   the Android emulator's alias for the host's loopback
-#   LAN_IP     a real phone on the same LAN, pre-WireGuard
-LOOPBACK_IP="127.0.0.1"
-EMULATOR_HOST_IP="10.0.2.2"
-LAN_IP="${LAN_IP:-192.168.1.168}"
-
-# Private key material: owner-only from the moment it exists, rather than
-# created world-readable and chmod'ed a beat later.
-umask 077
-mkdir -p "$CERTS_DIR"
-chmod 700 "$CERTS_DIR"
-cd "$CERTS_DIR"
-echo "==> Writing certificates to $CERTS_DIR"
-
-if [ -f ca.pem ]; then
-    echo "==> ca.pem already exists, reusing existing CA."
-else
-    echo "==> Generating CA key + self-signed CA certificate"
-    openssl ecparam -name prime256v1 -genkey -noout -out ca-key.pem
-    # Explicit keyUsage: strict verifiers (e.g. Python 3.14's ssl) reject a
-    # CA without it, and Android could follow -- cheap to be proper now,
-    # expensive to regenerate after phones have pinned it.
-    openssl req -new -x509 -key ca-key.pem -out ca.pem -days 3650 \
-        -subj "/O=ai-app dev/CN=ai-app dev CA" \
-        -addext "basicConstraints=critical,CA:TRUE" \
-        -addext "keyUsage=critical,keyCertSign,cRLSign"
-fi
-
-echo "==> Generating leaf key + CSR for $SERVER_IP (+ dev addresses)"
-openssl ecparam -name prime256v1 -genkey -noout -out leaf-key.pem
-openssl req -new -key leaf-key.pem -out leaf.csr \
-    -subj "/O=ai-app dev/CN=$SERVER_IP"
-
-echo "==> Signing leaf certificate with the dev CA"
-cat > leaf.ext <<EOF
-subjectAltName = IP:$SERVER_IP,IP:$LOOPBACK_IP,IP:$EMULATOR_HOST_IP,IP:$LAN_IP
-basicConstraints = CA:FALSE
-keyUsage = digitalSignature
-extendedKeyUsage = serverAuth
-EOF
-openssl x509 -req -in leaf.csr -CA ca.pem -CAkey ca-key.pem -CAcreateserial \
-    -out leaf.pem -days 3650 -extfile leaf.ext
-rm -f leaf.csr leaf.ext ca.srl
-
-echo "==> Computing certificate fingerprints (SPKI SHA-256)"
-CA_SHA256=$(openssl x509 -in ca.pem -pubkey -noout \
-    | openssl pkey -pubin -outform der \
-    | openssl dgst -sha256 -binary \
-    | openssl base64)
-echo "$CA_SHA256" > ca-sha256.txt
-LEAF_SHA256=$(openssl x509 -in leaf.pem -pubkey -noout \
-    | openssl pkey -pubin -outform der \
-    | openssl dgst -sha256 -binary \
-    | openssl base64)
-echo "$LEAF_SHA256" > leaf-sha256.txt
-
-echo
-echo "==> Done."
-echo "    CA fingerprint (base64):   $CA_SHA256"
-echo "    Leaf fingerprint (base64): $LEAF_SHA256"
-echo
-echo "    Only relevant if the CA was regenerated just now (i.e. ca.pem did"
-echo "    not already exist): the app embeds PINNED_CA_PEM and needs the new"
-echo "    $CERTS_DIR/ca.pem contents pasted in, or it silently"
-echo "    stops being able to reach this server. The app installs via Local"
-echo "    Updater, so recovery is a reinstall through that -- but it's still"
-echo "    a one-way door for the installed copy."
-echo
-echo "      app/androidApp/src/main/kotlin/com/example/aiapp/PinnedCert.kt"
-echo
-echo "    Only ca.pem is meant to leave this machine. Copy it by hand; do not"
-echo "    put the certs directory back in the repo, which is shared with the"
-echo "    VM (see this script's header)."

server/Cargo.lock

@@ -24,11 +24,12 @@ dependencies = [
  "anyhow",
  "axum",
  "axum-server",
- "base64",
+ "base64 0.23.1",
  "clap",
  "if-addrs",
  "qrcode",
  "rand",
+ "rcgen",
  "rustls",
  "serde",
  "serde_json",
@@ -109,6 +110,45 @@ dependencies = [
  "rustversion",
 ]
 
+[[package]]
+name = "asn1-rs"
+version = "0.7.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b7f43a50ac4fdca5df8e885c21b835997f0a1cdee65494a6847694a98652d9d8"
+dependencies = [
+ "asn1-rs-derive",
+ "asn1-rs-impl",
+ "displaydoc",
+ "nom",
+ "num-traits",
+ "rusticata-macros",
+ "thiserror",
+ "time",
+]
+
+[[package]]
+name = "asn1-rs-derive"
+version = "0.6.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3109e49b1e4909e9db6515a30c633684d68cdeaa252f215214cb4fa1a5bfee2c"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 2.0.119",
+ "synstructure",
+]
+
+[[package]]
+name = "asn1-rs-impl"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7b18050c2cd6fe86c3a76584ef5e0baf286d038cda203eb6223df2cc413565f7"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 2.0.119",
+]
+
 [[package]]
 name = "atomic-waker"
 version = "1.1.2"
@@ -219,12 +259,27 @@ dependencies = [
  "tower-service",
 ]
 
+[[package]]
+name = "base64"
+version = "0.22.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "72b3254f16251a8381aa12e40e3c4d2f0199f8c6508fbecb9d91f575e0fbb8c6"
+
 [[package]]
 name = "base64"
 version = "0.23.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "ac07cdecf99051d9a5238b80f35af32cdeba5b336e55d957b318b50137e18da5"
 
+[[package]]
+name = "bit-vec"
+version = "0.9.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b71798fca2c1fe1086445a7258a4bc81e6e49dcd24c8d0dd9a1e57395b603f51"
+dependencies = [
+ "serde",
+]
+
 [[package]]
 name = "bitflags"
 version = "2.13.1"
@@ -363,6 +418,32 @@ dependencies = [
  "hybrid-array",
 ]
 
+[[package]]
+name = "data-encoding"
+version = "2.11.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "4583a4551df46e2792f82ceeac45e850d2e2d5debba0b91f102385cda5b11f06"
+
+[[package]]
+name = "der-parser"
+version = "10.0.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "07da5016415d5a3c4dd39b11ed26f915f52fc4e0dc197d87908bc916e51bc1a6"
+dependencies = [
+ "asn1-rs",
+ "displaydoc",
+ "nom",
+ "num-bigint",
+ "num-traits",
+ "rusticata-macros",
+]
+
+[[package]]
+name = "deranged"
+version = "0.5.8"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7cd812cc2bc1d69d4764bd80df88b4317eaef9e773c75226407d9bc0876b211c"
+
 [[package]]
 name = "digest"
 version = "0.11.3"
@@ -374,6 +455,17 @@ dependencies = [
  "crypto-common",
 ]
 
+[[package]]
+name = "displaydoc"
+version = "0.2.7"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c6232dd377dcc64799954cbd3a9bb882e9cdc1308ccd87b1c098f1fb2eaf82a8"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 3.0.4",
+]
+
 [[package]]
 name = "dunce"
 version = "1.0.5"
@@ -740,6 +832,12 @@ version = "0.3.17"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6877bb514081ee2a7ff5ef9de3281f14a4dd4bceac4c09388074a6b5df8a139a"
 
+[[package]]
+name = "minimal-lexical"
+version = "0.2.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "68354c5c6bd36d73ff3feceb05efa59b6acb7626617f4962be322a825e61f79a"
+
 [[package]]
 name = "miniz_oxide"
 version = "0.8.9"
@@ -778,6 +876,16 @@ dependencies = [
  "version_check",
 ]
 
+[[package]]
+name = "nom"
+version = "7.1.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d273983c5a657a70a3e8f2a01329822f3b8c8172b73826411a55751e404a0a4a"
+dependencies = [
+ "memchr",
+ "minimal-lexical",
+]
+
 [[package]]
 name = "nu-ansi-term"
 version = "0.50.3"
@@ -787,6 +895,49 @@ dependencies = [
  "windows-sys 0.61.2",
 ]
 
+[[package]]
+name = "num-bigint"
+version = "0.4.8"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c89e69e7e0f03bea5ef08013795c25018e101932225a656383bd384495ecc367"
+dependencies = [
+ "num-integer",
+ "num-traits",
+]
+
+[[package]]
+name = "num-conv"
+version = "0.2.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "521739c6d2bac4aa25192232afe6841231376b2b26d4d9fae5ecf8ca5772e441"
+
+[[package]]
+name = "num-integer"
+version = "0.1.47"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7ce2d95d4b3734dc35aa2f45e1aa22cd416814592a4f9d9205e11affd5b8e10b"
+dependencies = [
+ "num-traits",
+]
+
+[[package]]
+name = "num-traits"
+version = "0.2.19"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "071dfc062690e90b734c0b2273ce72ad0ffa95f0c74596bc250dcfd960262841"
+dependencies = [
+ "autocfg",
+]
+
+[[package]]
+name = "oid-registry"
+version = "0.8.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "12f40cff3dde1b6087cc5d5f5d4d65712f34016a03ed60e9c08dcc392736b5b7"
+dependencies = [
+ "asn1-rs",
+]
+
 [[package]]
 name = "once_cell"
 version = "1.21.4"
@@ -799,6 +950,16 @@ version = "1.70.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "384b8ab6d37215f3c5301a95a4accb5d64aa607f1fcb26a11b5303878451b4fe"
 
+[[package]]
+name = "pem"
+version = "3.0.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "1d30c53c26bc5b31a98cd02d20f25a7c8567146caf63ed593a9d87b2775291be"
+dependencies = [
+ "base64 0.22.1",
+ "serde_core",
+]
+
 [[package]]
 name = "percent-encoding"
 version = "2.3.2"
@@ -817,6 +978,12 @@ version = "0.3.34"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "f6b464fbc74e149a392436b17d523f769e057cb6877f6a5c4618bc6f11800548"
 
+[[package]]
+name = "powerfmt"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "439ee305def115ba05938db6eb1644ff94165c5ab5e9420d1c1bcedbba909391"
+
 [[package]]
 name = "proc-macro2"
 version = "1.0.107"
@@ -864,6 +1031,20 @@ version = "0.10.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "63b8176103e19a2643978565ca18b50549f6101881c443590420e4dc998a3c69"
 
+[[package]]
+name = "rcgen"
+version = "0.14.9"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "091e7a8e7d86e6feb87a27ce8e2cba29d49eff9507afeebefab7eeb2ca667fb4"
+dependencies = [
+ "pem",
+ "ring",
+ "rustls-pki-types",
+ "time",
+ "x509-parser",
+ "yasna",
+]
+
 [[package]]
 name = "regex-automata"
 version = "0.4.18"
@@ -895,6 +1076,15 @@ dependencies = [
  "windows-sys 0.52.0",
 ]
 
+[[package]]
+name = "rusticata-macros"
+version = "4.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "faf0c4a6ece9950b9abdb62b1cfcf2a68b3b67a10ba445b3bb85be2a293d0632"
+dependencies = [
+ "nom",
+]
+
 [[package]]
 name = "rustix"
 version = "1.1.4"
@@ -1133,6 +1323,17 @@ version = "1.0.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "0bf256ce5efdfa370213c1dabab5935a12e49f2c58d15e9eac2870d3b4f27263"
 
+[[package]]
+name = "synstructure"
+version = "0.13.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "728a70f3dbaf5bab7f0c4b1ac8d7ae5ea60a4b5549c8a5914361c99147a709d2"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 2.0.119",
+]
+
 [[package]]
 name = "tempfile"
 version = "3.27.0"
@@ -1175,6 +1376,36 @@ dependencies = [
  "cfg-if",
 ]
 
+[[package]]
+name = "time"
+version = "0.3.55"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "cdb87b95ec50ddfa440816d227a17b2ccbdda963a316a727fda0fc4334f7d134"
+dependencies = [
+ "deranged",
+ "num-conv",
+ "powerfmt",
+ "serde_core",
+ "time-core",
+ "time-macros",
+]
+
+[[package]]
+name = "time-core"
+version = "0.1.9"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9e1c906769ad99c88eaa54e728060edef082f8e358ff32030cb7c7d315e81109"
+
+[[package]]
+name = "time-macros"
+version = "0.2.32"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7e689342a48d2ea927c87ea50cabf8594854bf940e9310208848d680d668ed85"
+dependencies = [
+ "num-conv",
+ "time-core",
+]
+
 [[package]]
 name = "tokio"
 version = "1.53.1"
@@ -1351,7 +1582,7 @@ version = "3.4.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "972d7902c8735f2695410b8aed7df6ed12a47394aa1c8d7af49f0497b731a94d"
 dependencies = [
- "base64",
+ "base64 0.23.1",
  "flate2",
  "log",
  "percent-encoding",
@@ -1368,7 +1599,7 @@ version = "0.6.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "da5f78b09e6941e1a0f2e30e695e4b120377b54d5e0aec11b594bb57b3971613"
 dependencies = [
- "base64",
+ "base64 0.23.1",
  "http",
  "httparse",
  "log",
@@ -1501,6 +1732,34 @@ version = "0.52.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "589f6da84c646204747d1270a2a5661ea66ed1cced2631d546fdfb155959f9ec"
 
+[[package]]
+name = "x509-parser"
+version = "0.18.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d43b0f71ce057da06bc0851b23ee24f3f86190b07203dd8f567d0b706a185202"
+dependencies = [
+ "asn1-rs",
+ "data-encoding",
+ "der-parser",
+ "lazy_static",
+ "nom",
+ "oid-registry",
+ "ring",
+ "rusticata-macros",
+ "thiserror",
+ "time",
+]
+
+[[package]]
+name = "yasna"
+version = "0.6.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b5f6765e852b9b4dc8e2a76843e4d64d1cea8e79bcde0b6901aea8e7c7f08282"
+dependencies = [
+ "bit-vec",
+ "time",
+]
+
 [[package]]
 name = "zeroize"
 version = "1.9.0"

server/Cargo.toml

@@ -30,6 +30,15 @@ qrcode = { version = "0.14", default-features = false }
 # The wg0-bound listener needs the interface's address; the stdlib has no
 # getifaddrs. This is the smallest crate that wraps just that.
 if-addrs = "0.15"
+# Generates this server's TLS certificates on first start, replacing a
+# setup script that shelled out to whatever openssl happened to be
+# installed. In process means one place decides the extensions, the file
+# modes, and which addresses the leaf covers. x509-parser so the issuer is
+# read back from the CA actually on disk: reconstructing it from the same
+# parameters would work only as long as nothing ever changed them, and a
+# mismatched issuer name yields a chain that fails to validate rather than
+# anything that looks wrong at generation time.
+rcgen = { version = "0.14", features = ["pem", "x509-parser"] }
 # Outbound HTTPS for the usage endpoint. A small blocking client fits an
 # every-few-minutes poll better than pulling in reqwest's tower stack;
 # rustls-backed like the rest of the TLS here.

server/src/certs.rs

@@ -0,0 +1,202 @@
+//! The TLS certificates this server presents, generated in process on
+//! first start.
+//!
+//! There used to be a `gen-dev-cert.sh` calling openssl, which meant a
+//! setup step to remember, a second place for the "which SANs?" answer to
+//! live, and a dependency on whatever openssl was installed. Doing it here
+//! means the server can simply ensure its own certificates exist, with the
+//! file modes and extensions it wants, and with the address it is actually
+//! about to bind already in the leaf.
+//!
+//! The split that matters is between the two:
+//!
+//! - The **CA** is generated once and then left alone. The app
+//!   pins it, so replacing it strands every installed copy -- recovery is
+//!   a reinstall over the plain-HTTP bootstrap port. It is the one thing
+//!   here that is a one-way door.
+//! - The **leaf** is cheap and reissued on every start, signed by that
+//!   same unchanged CA. Nothing pins it, so covering a new address is just
+//!   a restart rather than anything the phone has to be told about.
+//!
+//! Everything is written owner-only into a directory outside the repo (see
+//! `config_home`): the repo is a mount shared with a VM that is not
+//! trusted, and a CA private key that VM can read is one it can sign with
+//! -- a certificate signed by a pinned CA is accepted without question,
+//! which is exactly the attack pinning exists to stop.
+
+use std::net::IpAddr;
+use std::os::unix::fs::{DirBuilderExt, OpenOptionsExt, PermissionsExt};
+use std::path::{Path, PathBuf};
+
+use anyhow::{Context, Result};
+use rcgen::{
+    BasicConstraints, CertificateParams, DnType, IsCa, Issuer, KeyPair, KeyUsagePurpose, SanType,
+};
+
+/// Where the leaf lives, for handing to the TLS listener.
+pub struct Certificates {
+    pub leaf_cert: PathBuf,
+    pub leaf_key: PathBuf,
+    /// True when the CA was created just now, i.e. anything already
+    /// installed pins the wrong one and has to be reinstalled.
+    pub ca_is_new: bool,
+}
+
+/// Ensures `dir` holds a CA and a leaf covering `addresses`, creating what
+/// is missing. Safe to call on every start.
+pub fn ensure(dir: &Path, addresses: &[IpAddr]) -> Result<Certificates> {
+    std::fs::DirBuilder::new()
+        .recursive(true)
+        .mode(0o700)
+        .create(dir)
+        .with_context(|| format!("create {}", dir.display()))?;
+    // Set explicitly as well: `mode` applies only when the directory is
+    // created, so a directory that already existed -- made by hand, or by
+    // an older version -- would otherwise keep whatever permissions it had
+    // while holding a private key.
+    std::fs::set_permissions(dir, std::fs::Permissions::from_mode(0o700))
+        .with_context(|| format!("restrict {}", dir.display()))?;
+
+    let ca_cert_path = dir.join("ca.pem");
+    let ca_key_path = dir.join("ca-key.pem");
+    let ca_is_new = !ca_cert_path.is_file() || !ca_key_path.is_file();
+
+    let (ca_pem, ca_key_pem) = if ca_is_new {
+        let (pem, key) = generate_ca()?;
+        write_private(&ca_key_path, &key)?;
+        write_private(&ca_cert_path, &pem)?;
+        tracing::info!("generated a new CA in {}", dir.display());
+        (pem, key)
+    } else {
+        (
+            std::fs::read_to_string(&ca_cert_path)
+                .with_context(|| format!("read {}", ca_cert_path.display()))?,
+            std::fs::read_to_string(&ca_key_path)
+                .with_context(|| format!("read {}", ca_key_path.display()))?,
+        )
+    };
+
+    let (leaf_pem, leaf_key_pem) = generate_leaf(&ca_pem, &ca_key_pem, addresses)?;
+    let leaf_cert = dir.join("leaf.pem");
+    let leaf_key = dir.join("leaf-key.pem");
+    write_private(&leaf_key, &leaf_key_pem)?;
+    write_private(&leaf_cert, &leaf_pem)?;
+
+    Ok(Certificates { leaf_cert, leaf_key, ca_is_new })
+}
+
+fn generate_ca() -> Result<(String, String)> {
+    let key = KeyPair::generate().context("generate CA key")?;
+    let mut params = CertificateParams::default();
+    params.distinguished_name.push(DnType::OrganizationName, "ai-app dev");
+    params.distinguished_name.push(DnType::CommonName, "ai-app dev CA");
+    params.is_ca = IsCa::Ca(BasicConstraints::Unconstrained);
+    // Explicit, because strict verifiers reject a CA without them -- and
+    // that rejection surfaces as an opaque handshake failure on a phone.
+    params.key_usages = vec![KeyUsagePurpose::KeyCertSign, KeyUsagePurpose::CrlSign];
+    let certificate = params.self_signed(&key).context("self-sign CA")?;
+    Ok((certificate.pem(), key.serialize_pem()))
+}
+
+fn generate_leaf(
+    ca_pem: &str,
+    ca_key_pem: &str,
+    addresses: &[IpAddr],
+) -> Result<(String, String)> {
+    let ca_key = KeyPair::from_pem(ca_key_pem).context("read CA key")?;
+    let issuer = Issuer::from_ca_cert_pem(ca_pem, ca_key).context("read CA certificate")?;
+
+    let key = KeyPair::generate().context("generate leaf key")?;
+    let mut params = CertificateParams::default();
+    params.distinguished_name.push(DnType::OrganizationName, "ai-app dev");
+    params.distinguished_name.push(
+        DnType::CommonName,
+        addresses.first().map(|a| a.to_string()).unwrap_or_else(|| "dev-updater".to_string()),
+    );
+    params.subject_alt_names = addresses.iter().map(|a| SanType::IpAddress(*a)).collect();
+    params.is_ca = IsCa::ExplicitNoCa;
+    params.key_usages = vec![KeyUsagePurpose::DigitalSignature];
+    params.use_authority_key_identifier_extension = true;
+    let certificate = params.signed_by(&key, &issuer).context("sign leaf")?;
+    Ok((certificate.pem(), key.serialize_pem()))
+}
+
+/// Writes owner-readable only, from the moment the file exists rather than
+/// a `chmod` afterwards.
+fn write_private(path: &Path, contents: &str) -> Result<()> {
+    use std::io::Write;
+    let mut file = std::fs::OpenOptions::new()
+        .write(true)
+        .create(true)
+        .truncate(true)
+        .mode(0o600)
+        .open(path)
+        .with_context(|| format!("write {}", path.display()))?;
+    file.write_all(contents.as_bytes())
+        .with_context(|| format!("write {}", path.display()))
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    fn addresses() -> Vec<IpAddr> {
+        vec!["10.66.0.1".parse().unwrap(), "127.0.0.1".parse().unwrap()]
+    }
+
+    #[test]
+    fn generates_once_then_keeps_the_ca_and_reissues_the_leaf() {
+        let dir = tempfile::tempdir().expect("tempdir");
+
+        let first = ensure(dir.path(), &addresses()).expect("generate");
+        assert!(first.ca_is_new);
+        let ca = std::fs::read_to_string(dir.path().join("ca.pem")).expect("ca");
+        let leaf = std::fs::read_to_string(&first.leaf_cert).expect("leaf");
+        assert!(ca.starts_with("-----BEGIN CERTIFICATE-----"));
+
+        let second = ensure(dir.path(), &addresses()).expect("regenerate");
+        // The CA is the pinned one: replacing it would strand every
+        // installed app, so it must survive a restart untouched.
+        assert!(!second.ca_is_new);
+        assert_eq!(ca, std::fs::read_to_string(dir.path().join("ca.pem")).expect("ca"));
+        // The leaf is not pinned, and is reissued so a new address is just
+        // a restart away.
+        assert_ne!(leaf, std::fs::read_to_string(&second.leaf_cert).expect("leaf"));
+    }
+
+    #[test]
+    fn everything_is_owner_only() {
+        let dir = tempfile::tempdir().expect("tempdir");
+        let certs = ensure(dir.path(), &addresses()).expect("generate");
+        assert_eq!(
+            std::fs::metadata(dir.path()).expect("dir").permissions().mode() & 0o777,
+            0o700,
+        );
+        for file in ["ca.pem", "ca-key.pem", "leaf.pem", "leaf-key.pem"] {
+            let mode = std::fs::metadata(dir.path().join(file))
+                .expect(file)
+                .permissions()
+                .mode();
+            assert_eq!(mode & 0o777, 0o600, "{file} is not owner-only");
+        }
+        assert!(certs.leaf_key.is_file());
+    }
+
+    /// The pair has to be loadable by the TLS stack that will actually
+    /// serve it -- a "file exists" check wouldn't catch a key that doesn't
+    /// match its certificate, which fails at the first handshake instead.
+    #[tokio::test]
+    async fn the_leaf_loads_into_the_real_tls_config() {
+        // main() installs this; tests don't run main. Both rustls crypto
+        // providers are in the graph (ureq brings ring, axum-server
+        // aws-lc-rs), so rustls refuses to pick one on its own. Ignoring
+        // the result because another test may have installed it first.
+        let _ = rustls::crypto::aws_lc_rs::default_provider().install_default();
+
+        let dir = tempfile::tempdir().expect("tempdir");
+        let certs = ensure(dir.path(), &addresses()).expect("generate");
+        axum_server::tls_rustls::RustlsConfig::from_pem_file(&certs.leaf_cert, &certs.leaf_key)
+            .await
+            .expect("the generated leaf and key should load as a TLS identity");
+    }
+}

server/src/config.rs

@@ -12,7 +12,7 @@
 //! holds only the metadata needed to list and respawn sessions.
 
 use std::fs::File;
-use std::os::unix::fs::{DirBuilderExt, OpenOptionsExt};
+use std::os::unix::fs::{DirBuilderExt, OpenOptionsExt, PermissionsExt};
 use std::path::{Path, PathBuf};
 
 use anyhow::{Context, Result};
@@ -26,7 +26,13 @@ pub fn create_private_dir(dir: &Path) -> Result<()> {
         .recursive(true)
         .mode(0o700)
         .create(dir)
-        .with_context(|| format!("create {}", dir.display()))
+        .with_context(|| format!("create {}", dir.display()))?;
+    // Set explicitly as well: `mode` applies only when the directory is
+    // created, so one that already existed -- made by hand, or by a
+    // version that didn't do this -- would otherwise keep whatever
+    // permissions it had while holding transcripts.
+    std::fs::set_permissions(dir, std::fs::Permissions::from_mode(0o700))
+        .with_context(|| format!("restrict {}", dir.display()))
 }
 
 /// Opens `path` for writing, creating it owner-readable only.

server/src/main.rs

@@ -14,6 +14,7 @@
 //! unencrypted by misconfiguration -- even inside the tunnel.
 
 mod auth;
+mod certs;
 mod config;
 mod routes;
 mod session;
@@ -24,7 +25,7 @@ use std::net::{IpAddr, SocketAddr};
 use std::path::PathBuf;
 use std::sync::Arc;
 
-use anyhow::{Context, Result, bail};
+use anyhow::{Context, Result};
 use clap::Parser;
 
 use config::TokenEntry;
@@ -79,8 +80,8 @@ struct Args {
     #[arg(long)]
     data_dir: Option<PathBuf>,
 
-    /// Directory holding `leaf.pem`/`leaf-key.pem`, as produced by
-    /// `gen-dev-cert.sh`. Defaults to `$XDG_CONFIG_HOME/ai-app/certs`.
+    /// Directory holding the TLS certificates, generated here on first
+    /// start. Defaults to `$XDG_CONFIG_HOME/ai-app/certs`.
     #[arg(long)]
     certs: Option<PathBuf>,
 
@@ -90,6 +91,30 @@ struct Args {
     rotate_token: bool,
 }
 
+/// Every address this machine answers on, for the leaf's SANs -- so the
+/// certificate covers whatever the phone actually dials without anyone
+/// maintaining a hardcoded IP. In production that is the WireGuard
+/// address; loopback is included for curl and tests, and 10.0.2.2 is the
+/// alias an Android emulator reaches its host by, which is not a real
+/// interface anywhere.
+fn local_addresses() -> Vec<IpAddr> {
+    let mut addresses = vec![IpAddr::from([127, 0, 0, 1]), IpAddr::from([10, 0, 2, 2])];
+    match if_addrs::get_if_addrs() {
+        Ok(interfaces) => {
+            for interface in interfaces {
+                let ip = interface.ip();
+                if ip.is_ipv4() && !addresses.contains(&ip) {
+                    addresses.push(ip);
+                }
+            }
+        }
+        // Not fatal: the certificate still covers loopback, which is
+        // enough to start and to diagnose from the machine itself.
+        Err(err) => tracing::warn!("couldn't enumerate interfaces for the certificate: {err}"),
+    }
+    addresses
+}
+
 /// The IPv4 address on the WireGuard interface, or a refusal to start.
 /// Failing closed here (rather than falling back to a wider bind) is part
 /// of the security posture -- see the module doc comment.
@@ -157,6 +182,22 @@ async fn main() -> Result<()> {
         tracing::info!("  session {} ({}, {:?})", info.id, info.provider, info.status);
     }
 
+    // Before the interface check below, deliberately: the certificates are
+    // also what the phone app embeds at build time, so they need to be
+    // obtainable on a machine whose tunnel isn't up yet. The leaf is
+    // reissued on every start, so once wg0 exists the next start covers it.
+    let certs_dir = args.certs.unwrap_or_else(|| config_home().join("certs"));
+    let certificates = certs::ensure(&certs_dir, &local_addresses())
+        .with_context(|| format!("failed to prepare certificates in {}", certs_dir.display()))?;
+    if certificates.ca_is_new {
+        tracing::warn!(
+            "a new CA was generated in {} -- any installed app pins the previous one and can no \
+             longer reach this server. Rebuild it with app/build-apk.sh, which embeds this CA, \
+             and reinstall through Dev Updater.",
+            certs_dir.display(),
+        );
+    }
+
     let bind_ip = match args.bind {
         Some(ip) => {
             tracing::warn!(
@@ -183,19 +224,10 @@ async fn main() -> Result<()> {
         print_enrollment(bind_ip, args.port, &token)?;
     }
 
-    let certs_dir = args.certs.unwrap_or_else(|| config_home().join("certs"));
-    let leaf_cert = certs_dir.join("leaf.pem");
-    let leaf_key = certs_dir.join("leaf-key.pem");
-    if !leaf_cert.is_file() || !leaf_key.is_file() {
-        bail!(
-            "missing {} / {} -- run ./gen-dev-cert.sh on this machine first. The app pins the CA \
-             it generates and this server refuses to serve without TLS, so the private keys must \
-             be generated here and stay here.",
-            leaf_cert.display(),
-            leaf_key.display(),
-        );
-    }
-    let tls_config = axum_server::tls_rustls::RustlsConfig::from_pem_file(&leaf_cert, &leaf_key)
+    let tls_config = axum_server::tls_rustls::RustlsConfig::from_pem_file(
+        &certificates.leaf_cert,
+        &certificates.leaf_key,
+    )
     .await
     .context("failed to load TLS cert/key")?;
 

server/src/session/mod.rs

@@ -1,7 +1,7 @@
 //! The live session registry. Every session mutation -- spawn, delete,
 //! token changes -- funnels through [`SessionManager`] under one lock, so
 //! in-memory state and `config.json` can't come apart (the same pattern as
-//! local-updater's `registry.rs`).
+//! dev-updater's `registry.rs`).
 //!
 //! A live session is a driver plus one event pump: the driver reports
 //! [`Event`]s into an mpsc channel; the pump assigns each a sequence

test-wg-tunnel.sh

@@ -14,8 +14,8 @@
 # The veth pair stands in for "the internet" carrying WireGuard's UDP; the
 # wg interfaces are real, with a real handshake and real keys. 10.66.0.1 is
 # deliberately the same address the leaf certificate carries a SAN for
-# (gen-dev-cert.sh), so a client inside the tunnel completes the same
-# pinned-TLS handshake a phone will.
+# (certs.rs covers every local address), so a client inside the tunnel
+# completes the same pinned-TLS handshake a phone will.
 #
 #   ./test-wg-tunnel.sh up      create the tunnel (needs sudo)
 #   ./test-wg-tunnel.sh test    run the server on wg0 and reach it from "phone"
@@ -80,8 +80,9 @@ up() {
 }
 
 test_tunnel() {
-    if [ ! -f "$REPO/certs/leaf.pem" ]; then
-        echo "No certs/ -- run ./gen-dev-cert.sh first." >&2
+    CERTS="${XDG_CONFIG_HOME:-$HOME/.config}/ai-app/certs"
+    if [ ! -f "$CERTS/leaf.pem" ]; then
+        echo "No certificates in $CERTS -- start ai-server once; it makes them." >&2
         exit 1
     fi
     if [ ! -x "$REPO/server/target/debug/ai-server" ]; then
@@ -98,13 +99,12 @@ test_tunnel() {
     ss -tlnp 2>/dev/null | grep 8443 | sed 's/^/    /' || echo "    (nothing on 8443)"
 
     echo "==> From inside the tunnel: GET /sessions through wg1 -> wg0"
-    TOKEN=$(sudo cat "$REPO/config.json" 2>/dev/null | sed -n 's/.*"sha256": "\(.*\)".*/\1/p' | head -1)
     if [ -z "${AI_TOKEN:-}" ]; then
         echo "    (set AI_TOKEN=<the enrollment token> to test an authorized call;"
         echo "     without it this only proves reachability + TLS, via a 401)"
     fi
     sudo ip netns exec "$NS" curl -s -o /dev/null -w "    HTTP %{http_code} (TLS ok, pinned CA)\n" \
-        --cacert "$REPO/certs/ca.pem" \
+        --cacert "$CERTS/ca.pem" \
         ${AI_TOKEN:+-H "Authorization: Bearer $AI_TOKEN"} \
         "https://$SERVER_WG_IP:8443/sessions" || echo "    UNREACHABLE"