diff --git a/bridge/src/main/scala/protocbridge/frontend/PluginFrontend.scala b/bridge/src/main/scala/protocbridge/frontend/PluginFrontend.scala
index 7415f06..ec7d6ca 100644
--- a/bridge/src/main/scala/protocbridge/frontend/PluginFrontend.scala
+++ b/bridge/src/main/scala/protocbridge/frontend/PluginFrontend.scala
@@ -5,8 +5,6 @@ import java.nio.file.{Files, Path}
 
 import protocbridge.{ProtocCodeGenerator, ExtraEnv}
 
-import scala.util.Try
-
 /** A PluginFrontend instance provides a platform-dependent way for protoc to
   * communicate with a JVM based ProtocCodeGenerator.
   *
@@ -47,13 +45,7 @@ object PluginFrontend {
       gen: ProtocCodeGenerator,
       request: Array[Byte]
   ): Array[Byte] = {
-    Try {
-      gen.run(request)
-    }.recover { case throwable =>
-      createCodeGeneratorResponseWithError(
-        throwable.toString + "\n" + getStackTrace(throwable)
-      )
-    }.get
+    gen.run(request)
   }
 
   def createCodeGeneratorResponseWithError(error: String): Array[Byte] = {
@@ -116,9 +108,17 @@ object PluginFrontend {
       gen: ProtocCodeGenerator,
       fsin: InputStream,
       env: ExtraEnv
-  ): Array[Byte] = {
+  ): Array[Byte] = try {
     val bytes = readInputStreamToByteArrayWithEnv(fsin, env)
     runWithBytes(gen, bytes)
+  } catch {
+    // This covers all Throwable including OutOfMemoryError, StackOverflowError, etc.
+    // We need to make a best effort to return a response to protoc,
+    // otherwise protoc can hang indefinitely.
+    case throwable: Throwable =>
+      createCodeGeneratorResponseWithError(
+        throwable.toString + "\n" + getStackTrace(throwable)
+      )
   }
 
   def createTempFile(extension: String, content: String): Path = {
diff --git a/bridge/src/main/scala/protocbridge/frontend/PosixPluginFrontend.scala b/bridge/src/main/scala/protocbridge/frontend/PosixPluginFrontend.scala
index 5f70120..ef57687 100644
--- a/bridge/src/main/scala/protocbridge/frontend/PosixPluginFrontend.scala
+++ b/bridge/src/main/scala/protocbridge/frontend/PosixPluginFrontend.scala
@@ -40,6 +40,11 @@ object PosixPluginFrontend extends PluginFrontend {
         val response = PluginFrontend.runWithInputStream(plugin, fsin, env)
         fsin.close()
 
+        // Note that the output pipe must be opened after the input pipe is consumed.
+        // Otherwise, there might be a deadlock that
+        // - The shell script is stuck writing to the input pipe (which has a full buffer),
+        //   and doesn't open the write end of the output pipe.
+        // - This thread is stuck waiting for the write end of the output pipe to be opened.
         val fsout = Files.newOutputStream(outputPipe)
         fsout.write(response)
         fsout.close()
diff --git a/bridge/src/test/scala/protocbridge/frontend/OsSpecificFrontendSpec.scala b/bridge/src/test/scala/protocbridge/frontend/OsSpecificFrontendSpec.scala
new file mode 100644
index 0000000..a65bfd2
--- /dev/null
+++ b/bridge/src/test/scala/protocbridge/frontend/OsSpecificFrontendSpec.scala
@@ -0,0 +1,112 @@
+package protocbridge.frontend
+
+import org.apache.commons.io.IOUtils
+import org.scalatest.exceptions.TestFailedException
+import org.scalatest.flatspec.AnyFlatSpec
+import org.scalatest.matchers.must.Matchers
+import protocbridge.{ExtraEnv, ProtocCodeGenerator}
+
+import java.io.ByteArrayOutputStream
+import scala.concurrent.ExecutionContext.Implicits.global
+import scala.concurrent.duration.DurationInt
+import scala.concurrent.{Await, Future, TimeoutException}
+import scala.sys.process.ProcessIO
+import scala.util.Random
+
+class OsSpecificFrontendSpec extends AnyFlatSpec with Matchers {
+
+  protected def testPluginFrontend(
+      frontend: PluginFrontend,
+      generator: ProtocCodeGenerator,
+      env: ExtraEnv,
+      request: Array[Byte]
+  ): (frontend.InternalState, Array[Byte]) = {
+    val (path, state) = frontend.prepare(
+      generator,
+      env
+    )
+    val actualOutput = new ByteArrayOutputStream()
+    val process = sys.process
+      .Process(path.toAbsolutePath.toString)
+      .run(
+        new ProcessIO(
+          writeInput => {
+            writeInput.write(request)
+            writeInput.close()
+          },
+          processOutput => {
+            IOUtils.copy(processOutput, actualOutput)
+            processOutput.close()
+          },
+          processError => {
+            IOUtils.copy(processError, System.err)
+            processError.close()
+          }
+        )
+      )
+    try {
+      Await.result(Future { process.exitValue() }, 5.seconds)
+    } catch {
+      case _: TimeoutException =>
+        System.err.println(s"Timeout")
+        process.destroy()
+    }
+    frontend.cleanup(state)
+    (state, actualOutput.toByteArray)
+  }
+
+  protected def testSuccess(frontend: PluginFrontend): Unit = {
+    val random = new Random()
+    val toSend = Array.fill(123)(random.nextInt(256).toByte)
+    val toReceive = Array.fill(456)(random.nextInt(256).toByte)
+    val env = new ExtraEnv(secondaryOutputDir = "tmp")
+
+    val fakeGenerator = new ProtocCodeGenerator {
+      override def run(request: Array[Byte]): Array[Byte] = {
+        request mustBe (toSend ++ env.toByteArrayAsField)
+        toReceive
+      }
+    }
+    // Repeat 100,000 times since named pipes on macOS are flaky.
+    val repeatCount = 100000
+    for (i <- 1 until repeatCount) {
+      if (i % 100 == 1) println(s"Running iteration $i of $repeatCount")
+      val (state, response) =
+        testPluginFrontend(frontend, fakeGenerator, env, toSend)
+      try {
+        response mustBe toReceive
+      } catch {
+        case e: TestFailedException =>
+          System.err.println(
+            s"""Failed on iteration $i of $repeatCount: ${e.getMessage}"""
+          )
+      }
+    }
+    val (state, response) =
+      testPluginFrontend(frontend, fakeGenerator, env, toSend)
+    try {
+      response mustBe toReceive
+    } catch {
+      case e: TestFailedException =>
+        System.err.println(
+          s"""Failed on iteration $repeatCount of $repeatCount: ${e.getMessage}"""
+        )
+    }
+    state
+  }
+
+  protected def testFailure(frontend: PluginFrontend): Unit = {
+    val random = new Random()
+    val toSend = Array.fill(123)(random.nextInt(256).toByte)
+    val env = new ExtraEnv(secondaryOutputDir = "tmp")
+
+    val fakeGenerator = new ProtocCodeGenerator {
+      override def run(request: Array[Byte]): Array[Byte] = {
+        throw new OutOfMemoryError("test error")
+      }
+    }
+    val (_, response) =
+      testPluginFrontend(frontend, fakeGenerator, env, toSend)
+    response.length must be > 0
+  }
+}
diff --git a/bridge/src/test/scala/protocbridge/frontend/PosixPluginFrontendSpec.scala b/bridge/src/test/scala/protocbridge/frontend/PosixPluginFrontendSpec.scala
new file mode 100644
index 0000000..2a3481c
--- /dev/null
+++ b/bridge/src/test/scala/protocbridge/frontend/PosixPluginFrontendSpec.scala
@@ -0,0 +1,13 @@
+package protocbridge.frontend
+
+class PosixPluginFrontendSpec extends OsSpecificFrontendSpec {
+  if (!PluginFrontend.isWindows) {
+    it must "execute a program that forwards input and output to given stream" in {
+      testSuccess(PosixPluginFrontend)
+    }
+
+    it must "not hang if there is an OOM in generator" in {
+      testFailure(PosixPluginFrontend)
+    }
+  }
+}
diff --git a/bridge/src/test/scala/protocbridge/frontend/WindowsPluginFrontendSpec.scala b/bridge/src/test/scala/protocbridge/frontend/WindowsPluginFrontendSpec.scala
index 6385ad7..4bf39de 100644
--- a/bridge/src/test/scala/protocbridge/frontend/WindowsPluginFrontendSpec.scala
+++ b/bridge/src/test/scala/protocbridge/frontend/WindowsPluginFrontendSpec.scala
@@ -1,38 +1,13 @@
 package protocbridge.frontend
 
-import java.io.ByteArrayInputStream
-
-import protocbridge.{ProtocCodeGenerator, ExtraEnv}
-
-import scala.sys.process.ProcessLogger
-import org.scalatest.flatspec.AnyFlatSpec
-import org.scalatest.matchers.must.Matchers
-
-class WindowsPluginFrontendSpec extends AnyFlatSpec with Matchers {
+class WindowsPluginFrontendSpec extends OsSpecificFrontendSpec {
   if (PluginFrontend.isWindows) {
     it must "execute a program that forwards input and output to given stream" in {
-      val toSend = "ping"
-      val toReceive = "pong"
-      val env = new ExtraEnv(secondaryOutputDir = "tmp")
+      testSuccess(WindowsPluginFrontend)
+    }
 
-      val fakeGenerator = new ProtocCodeGenerator {
-        override def run(request: Array[Byte]): Array[Byte] = {
-          request mustBe (toSend.getBytes ++ env.toByteArrayAsField)
-          toReceive.getBytes
-        }
-      }
-      val (path, state) = WindowsPluginFrontend.prepare(
-        fakeGenerator,
-        env
-      )
-      val actualOutput = scala.collection.mutable.Buffer.empty[String]
-      val process = sys.process
-        .Process(path.toAbsolutePath.toString)
-        .#<(new ByteArrayInputStream(toSend.getBytes))
-        .run(ProcessLogger(o => actualOutput.append(o)))
-      process.exitValue()
-      actualOutput.mkString mustBe toReceive
-      WindowsPluginFrontend.cleanup(state)
+    it must "not hang if there is an OOM in generator" in {
+      testFailure(WindowsPluginFrontend)
     }
   }
 }