Do not crash when installing shutdown hook (#3456)

* Do not crash when installing shutdown hook

* Changelog

Author: romtsn

CHANGELOG.md

@@ -10,6 +10,7 @@
 ### Fixes
 
 - Fix faulty `span.frame_delay` calculation for early app start spans ([#3427](https://github.com/getsentry/sentry-java/pull/3427))
+- Fix crash when installing `ShutdownHookIntegration` and the VM is shutting down ([#3456](https://github.com/getsentry/sentry-java/pull/3456))
 
 ## 7.9.0
 

sentry/src/main/java/io/sentry/ShutdownHookIntegration.java

@@ -33,9 +33,12 @@ public void register(final @NotNull IHub hub, final @NotNull SentryOptions optio
 
     if (options.isEnableShutdownHook()) {
       thread = new Thread(() -> hub.flush(options.getFlushTimeoutMillis()));
-      runtime.addShutdownHook(thread);
-      options.getLogger().log(SentryLevel.DEBUG, "ShutdownHookIntegration installed.");
-      addIntegrationToSdkVersion(getClass());
+      handleShutdownInProgress(
+          () -> {
+            runtime.addShutdownHook(thread);
+            options.getLogger().log(SentryLevel.DEBUG, "ShutdownHookIntegration installed.");
+            addIntegrationToSdkVersion(getClass());
+          });
     } else {
       options.getLogger().log(SentryLevel.INFO, "enableShutdownHook is disabled.");
     }
@@ -44,16 +47,22 @@ public void register(final @NotNull IHub hub, final @NotNull SentryOptions optio
   @Override
   public void close() throws IOException {
     if (thread != null) {
-      try {
-        runtime.removeShutdownHook(thread);
-      } catch (IllegalStateException e) {
-        @Nullable final String message = e.getMessage();
-        // https://github.com/openjdk/jdk/blob/09b8a1959771213cb982d062f0a913285e4a0c6e/src/java.base/share/classes/java/lang/ApplicationShutdownHooks.java#L83
-        if (message != null && message.equals("Shutdown in progress")) {
-          // ignore
-        } else {
-          throw e;
-        }
+      handleShutdownInProgress(() -> runtime.removeShutdownHook(thread));
+    }
+  }
+
+  private void handleShutdownInProgress(final @NotNull Runnable runnable) {
+    try {
+      runnable.run();
+    } catch (IllegalStateException e) {
+      @Nullable final String message = e.getMessage();
+      // https://github.com/openjdk/jdk/blob/09b8a1959771213cb982d062f0a913285e4a0c6e/src/java.base/share/classes/java/lang/ApplicationShutdownHooks.java#L83
+      if (message != null
+          && (message.equals("Shutdown in progress")
+              || message.equals("VM already shutting down"))) {
+        // ignore
+      } else {
+        throw e;
       }
     }
   }

sentry/src/test/java/io/sentry/ShutdownHookIntegrationTest.kt

@@ -92,6 +92,16 @@ class ShutdownHookIntegrationTest {
         verify(fixture.runtime).removeShutdownHook(any())
     }
 
+    @Test
+    fun `shutdown in progress is handled gracefully for registration`() {
+        val integration = fixture.getSut()
+        whenever(fixture.runtime.addShutdownHook(any())).thenThrow(java.lang.IllegalStateException("VM already shutting down"))
+
+        integration.register(fixture.hub, fixture.options)
+
+        verify(fixture.runtime).addShutdownHook(any())
+    }
+
     @Test
     fun `non shutdown in progress during removeShutdownHook is rethrown`() {
         val integration = fixture.getSut()