Fix running unsigned apps locally on macOS Ventura (#2617)

Normally macOS Gatekeeper does not allow unsigned apps to run.
However, apps created on the same machine were allowed to run.
This allows developers to test package apps on their machines
without configuring Apple Developer ID.

Previously, the Compose Multiplatform Gradle plugin
simply did not do anything, when the signing was not configured.
However, in macOS Ventura the Gatekeeper checks
became stricker, so "unsigned" packaged apps started to
be shown as "damaged".

This seems to happen, because parts of a final app image
were signed. Also they were signed by different certificates
(a runtime image could be signed by a runtime vendor,
while Skiko binary is signed by JetBrains).

This change removes all signatures if signing is not configured.

See also https://bugs.openjdk.org/browse/JDK-8276150

Fixes #2476

gradle-plugins/compose/src/main/kotlin/org/jetbrains/compose/desktop/application/internal/MacSigner.kt

@@ -6,19 +6,54 @@
 package org.jetbrains.compose.desktop.application.internal
 
 import org.jetbrains.compose.desktop.application.internal.validation.ValidatedMacOSSigningSettings
+import org.jetbrains.compose.internal.utils.Arch
 import org.jetbrains.compose.internal.utils.MacUtils
+import org.jetbrains.compose.internal.utils.currentArch
 import java.io.File
-import java.nio.file.Files
 import java.util.regex.Pattern
+import kotlin.io.path.isExecutable
 
-internal class MacSigner(
+internal abstract class MacSigner(protected val runTool: ExternalToolRunner) {
-    val settings: ValidatedMacOSSigningSettings,
+    /**
-    private val runExternalTool: ExternalToolRunner
+     * If [entitlements] file is provided, executables are signed with entitlements.
-) {
+     * Set [forceEntitlements] to `true` to sign all types of files with the provided [entitlements].
+     */
+    abstract fun sign(
+        file: File,
+        entitlements: File? = null,
+        forceEntitlements: Boolean = false
+    )
+
+    fun unsign(file: File) {
+        runTool.unsign(file)
+    }
+
+    abstract val settings: ValidatedMacOSSigningSettings?
+}
+
+internal class NoCertificateSigner(runTool: ExternalToolRunner) : MacSigner(runTool) {
+    override fun sign(file: File, entitlements: File?, forceEntitlements: Boolean) {
+        unsign(file)
+        if (currentArch == Arch.Arm64) {
+            // Apple Silicon requires binaries to be signed
+            // For local builds, ad hoc signatures are OK
+            // https://wiki.lazarus.freepascal.org/Code_Signing_for_macOS
+            runTool.codesign("--sign", "-", "-vvvv", file.absolutePath)
+        }
+    }
+
+    override val settings: ValidatedMacOSSigningSettings?
+        get() = null
+}
+
+internal class MacSignerImpl(
+    override val settings: ValidatedMacOSSigningSettings,
+    runTool: ExternalToolRunner
+) : MacSigner(runTool)  {
     private lateinit var signKey: String
 
     init {
-        runExternalTool(
+        runTool(
             MacUtils.security,
             args = listOfNotNull(
                 "find-certificate",
@@ -27,58 +62,26 @@ internal class MacSigner(
                 settings.fullDeveloperID,
                 settings.keychain?.absolutePath
             ),
-            processStdout = { stdout ->
+            processStdout = { signKey = matchCertificates(it) }
-                signKey = findCertificate(stdout)
-            }
         )
     }
 
-    /**
+    override fun sign(
-     * If [entitlements] file is provided, executables are signed with entitlements.
-     * Set [forceEntitlements] to `true` to sign all types of files with the provided [entitlements].
-     */
-    fun sign(
         file: File,
-        entitlements: File? = null,
+        entitlements: File?,
-        forceEntitlements: Boolean = false
+        forceEntitlements: Boolean
     ) {
-        val args = arrayListOf(
+        runTool.unsign(file)
-            "-vvvv",
+        runTool.sign(
-            "--timestamp",
+            file = file,
-            "--options", "runtime",
+            signKey = signKey,
-            "--force",
+            entitlements = entitlements?.takeIf { forceEntitlements || file.isExecutable },
-            "--prefix", settings.prefix,
+            prefix = settings.prefix,
-            "--sign", signKey
+            keychain = settings.keychain
         )
-
-        settings.keychain?.let {
-            args.add("--keychain")
-            args.add(it.absolutePath)
-        }
-
-        if (forceEntitlements || Files.isExecutable(file.toPath())) {
-            entitlements?.let {
-                args.add("--entitlements")
-                args.add(it.absolutePath)
-            }
-        }
-
-        args.add(file.absolutePath)
-
-        runExternalTool(MacUtils.codesign, args)
     }
 
-    fun unsign(file: File) {
+    private fun matchCertificates(certificates: String): String {
-        val args = listOf(
-            "-vvvv",
-            "--remove-signature",
-            file.absolutePath
-        )
-        runExternalTool(MacUtils.codesign, args)
-
-    }
-
-    private fun findCertificate(certificates: String): String {
         val regex = Pattern.compile("\"alis\"<blob>=\"([^\"]+)\"")
         val m = regex.matcher(certificates)
         if (!m.find()) {
@@ -97,4 +100,34 @@ internal class MacSigner(
             )
         return result
     }
-}
+}
+
+private fun ExternalToolRunner.codesign(vararg args: String) =
+    this(MacUtils.codesign, args.toList())
+
+private fun ExternalToolRunner.unsign(file: File) =
+    codesign("-vvvv", "--remove-signature", file.absolutePath)
+
+private fun ExternalToolRunner.sign(
+    file: File,
+    signKey: String,
+    entitlements: File?,
+    prefix: String?,
+    keychain: File?
+) = codesign(
+    "-vvvv",
+    "--timestamp",
+    "--options", "runtime",
+    "--force",
+    *optionalArg("--prefix", prefix),
+    "--sign", signKey,
+    *optionalArg("--keychain", keychain?.absolutePath),
+    *optionalArg("--entitlements", entitlements?.absolutePath),
+    file.absolutePath
+)
+
+private fun optionalArg(arg: String, value: String?): Array<String> =
+    if (value != null) arrayOf(arg, value) else emptyArray()
+
+private val File.isExecutable: Boolean
+    get() = toPath().isExecutable()

gradle-plugins/compose/src/main/kotlin/org/jetbrains/compose/desktop/application/internal/MacSigningHelper.kt

@@ -7,9 +7,9 @@ package org.jetbrains.compose.desktop.application.internal
 
 import org.jetbrains.compose.desktop.application.internal.files.isDylibPath
 import java.io.File
+import java.nio.file.*
 import kotlin.io.path.isExecutable
 import kotlin.io.path.isRegularFile
-import kotlin.io.path.isSymbolicLink
 
 internal class MacSigningHelper(
     private val macSigner: MacSigner,
@@ -23,58 +23,18 @@ internal class MacSigningHelper(
     private val runtimeDir = appDir.resolve("Contents/runtime")
 
     fun modifyRuntimeIfNeeded() {
-        // Only resign modify the runtime if a provisioning profile or alternative entitlements file is provided.
-        // If no entitlements file is provided, the runtime cannot be resigned.
-        if (runtimeProvisioningProfile == null &&
-            // When resigning the runtime, an app entitlements file is also needed.
-            (runtimeEntitlementsFile == null || entitlementsFile == null)
-        ) {
-            return
-        }
 
-        // Add the provisioning profile
-        runtimeProvisioningProfile?.let {
-            addRuntimeProvisioningProfile(runtimeDir, it)
-        }
 
         // Resign the runtime completely (and also the app dir only)
-        resignRuntimeAndAppDir(appDir, runtimeDir)
-    }
-
-    private fun addRuntimeProvisioningProfile(
-        runtimeDir: File,
-        runtimeProvisioningProfile: File
-    ) {
-        runtimeProvisioningProfile.copyTo(
-            target = runtimeDir.resolve("Contents/embedded.provisionprofile"),
-            overwrite = true
-        )
-    }
-
-    private fun resignRuntimeAndAppDir(
-        appDir: File,
-        runtimeDir: File
-    ) {
         // Sign all libs and executables in runtime
         runtimeDir.walk().forEach { file ->
             val path = file.toPath()
-            if (path.isRegularFile() && (path.isExecutable() || path.toString().isDylibPath)) {
+            if (path.isRegularFile(LinkOption.NOFOLLOW_LINKS) && (path.isExecutable() || file.name.isDylibPath)) {
-                if (path.isSymbolicLink()) {
+                macSigner.sign(file, runtimeEntitlementsFile)
-                    // Ignore symbolic links
-                } else {
-                    // Resign file
-                    macSigner.unsign(file)
-                    macSigner.sign(file, runtimeEntitlementsFile)
-                }
             }
         }
 
-        // Resign runtime directory
-        macSigner.unsign(runtimeDir)
         macSigner.sign(runtimeDir, runtimeEntitlementsFile, forceEntitlements = true)
-
-        // Resign app directory (contents other than runtime were already signed by jpackage)
-        macSigner.unsign(appDir)
         macSigner.sign(appDir, entitlementsFile, forceEntitlements = true)
     }
 }

gradle-plugins/compose/src/main/kotlin/org/jetbrains/compose/desktop/application/tasks/AbstractJPackageTask.kt

@@ -23,11 +23,14 @@ import org.jetbrains.compose.desktop.application.internal.JvmRuntimeProperties
 import org.jetbrains.compose.desktop.application.internal.validation.validate
 import org.jetbrains.compose.internal.utils.*
 import java.io.*
+import java.nio.file.LinkOption
 import java.util.*
 import javax.inject.Inject
 import kotlin.collections.HashMap
 import kotlin.collections.HashSet
 import kotlin.collections.ArrayList
+import kotlin.io.path.isExecutable
+import kotlin.io.path.isRegularFile
 
 abstract class AbstractJPackageTask @Inject constructor(
     @get:Input
@@ -237,12 +240,17 @@ abstract class AbstractJPackageTask @Inject constructor(
     @get:Nested
     internal var nonValidatedMacSigningSettings: MacOSSigningSettings? = null
 
+    private val shouldSign: Boolean
+        get() = nonValidatedMacSigningSettings?.sign?.get() == true
+
     private val macSigner: MacSigner? by lazy {
         val nonValidatedSettings = nonValidatedMacSigningSettings
-        if (currentOS == OS.MacOS && nonValidatedSettings?.sign?.get() == true) {
+        if (currentOS == OS.MacOS) {
-            val validatedSettings =
+            if (shouldSign) {
-                nonValidatedSettings.validate(nonValidatedMacBundleID, project, macAppStore)
+                val validatedSettings =
-            MacSigner(validatedSettings, runExternalTool)
+                    nonValidatedSettings!!.validate(nonValidatedMacBundleID, project, macAppStore)
+                MacSignerImpl(validatedSettings, runExternalTool)
+            } else NoCertificateSigner(runExternalTool)
         } else null
     }
 
@@ -389,11 +397,11 @@ abstract class AbstractJPackageTask @Inject constructor(
             cliArg("--mac-app-category", macAppCategory)
             cliArg("--mac-entitlements", macEntitlementsFile)
 
-            macSigner?.let { signer ->
+            macSigner?.settings?.let { signingSettings ->
                 cliArg("--mac-sign", true)
-                cliArg("--mac-signing-key-user-name", signer.settings.identity)
+                cliArg("--mac-signing-key-user-name", signingSettings.identity)
-                cliArg("--mac-signing-keychain", signer.settings.keychain)
+                cliArg("--mac-signing-keychain", signingSettings.keychain)
-                cliArg("--mac-package-signing-prefix", signer.settings.prefix)
+                cliArg("--mac-package-signing-prefix", signingSettings.prefix)
             }
         }
     }
@@ -434,19 +442,16 @@ abstract class AbstractJPackageTask @Inject constructor(
         return outdatedLibs
     }
 
+    private fun jarCopyingProcessor(): FileCopyingProcessor =
+        if (currentOS == OS.MacOS) {
+            val tmpDirForSign = signDir.ioFile
+            fileOperations.clearDirs(tmpDirForSign)
+            MacJarSignFileCopyingProcessor(macSigner!!, tmpDirForSign, jvmRuntimeInfo.majorVersion)
+        } else SimpleFileCopyingProcessor
+
     override fun prepareWorkingDir(inputChanges: InputChanges) {
         val libsDir = libsDir.ioFile
-        val fileProcessor =
+        val fileProcessor = jarCopyingProcessor()
-            macSigner?.let { signer ->
-                val tmpDirForSign = signDir.ioFile
-                fileOperations.clearDirs(tmpDirForSign)
-
-                MacJarSignFileCopyingProcessor(
-                    signer,
-                    tmpDirForSign,
-                    jvmRuntimeVersion = jvmRuntimeInfo.majorVersion
-                )
-            } ?: SimpleFileCopyingProcessor
 
         val mangleJarFilesNames = mangleJarFilesNames.get()
         fun copyFileToLibsDir(sourceFile: File): File {
@@ -525,17 +530,30 @@ abstract class AbstractJPackageTask @Inject constructor(
 
     private fun modifyRuntimeOnMacOsIfNeeded() {
         if (currentOS != OS.MacOS || targetFormat != TargetFormat.AppImage) return
-        macSigner?.let { macSigner ->
+
-            val macSigningHelper = MacSigningHelper(
+        val appDir = destinationDir.ioFile.resolve("${packageName.get()}.app")
-                macSigner = macSigner,
+        val runtimeDir = appDir.resolve("Contents/runtime")
-                runtimeProvisioningProfile = macRuntimeProvisioningProfile.ioFileOrNull,
+
-                entitlementsFile = macEntitlementsFile.ioFileOrNull,
+        // Add the provisioning profile
-                runtimeEntitlementsFile = macRuntimeEntitlementsFile.ioFileOrNull,
+        macRuntimeProvisioningProfile.ioFileOrNull?.copyTo(
-                destinationDir = destinationDir.ioFile,
+            target = runtimeDir.resolve("Contents/embedded.provisionprofile"),
-                packageName = packageName.get()
+            overwrite = true
-            )
+        )
-            macSigningHelper.modifyRuntimeIfNeeded()
+        val appEntitlementsFile = macEntitlementsFile.ioFileOrNull
+        val runtimeEntitlementsFile = macRuntimeEntitlementsFile.ioFileOrNull
+
+        val macSigner = macSigner!!
+        // Resign the runtime completely (and also the app dir only)
+        // Sign all libs and executables in runtime
+        runtimeDir.walk().forEach { file ->
+            val path = file.toPath()
+            if (path.isRegularFile(LinkOption.NOFOLLOW_LINKS) && (path.isExecutable() || file.name.isDylibPath)) {
+                macSigner.sign(file, runtimeEntitlementsFile)
+            }
         }
+
+        macSigner.sign(runtimeDir, runtimeEntitlementsFile, forceEntitlements = true)
+        macSigner.sign(appDir, appEntitlementsFile, forceEntitlements = true)
     }
 
     override fun initState() {