diff --git a/Sources/NIO/System.swift b/Sources/NIO/System.swift
index d13c0863209..bd01f850cf4 100644
--- a/Sources/NIO/System.swift
+++ b/Sources/NIO/System.swift
@@ -150,6 +150,7 @@ private func preconditionIsNotUnacceptableErrno(err: CInt, where function: Strin
 @inline(__always)
 @discardableResult
 internal func syscall<T: FixedWidthInteger>(blocking: Bool,
+                                            eprototypeWorkaround: Bool = false,
                                             where function: String = #function,
                                             _ body: () throws -> T)
         throws -> IOResult<T> {
@@ -157,11 +158,18 @@ internal func syscall<T: FixedWidthInteger>(blocking: Bool,
         let res = try body()
         if res == -1 {
             let err = errno
-            switch (err, blocking) {
-            case (EINTR, _):
+            switch (err, blocking, eprototypeWorkaround) {
+            case (EINTR, _, _):
                 continue
-            case (EWOULDBLOCK, true):
+            case (EWOULDBLOCK, true, _):
                 return .wouldBlock(0)
+            #if os(macOS) || os(iOS) || os(watchOS) || os(tvOS)
+            case (EPROTOTYPE, _, true):
+                // EPROTOTYPE can, on Darwin platforms, sometimes fire due to a race in the XNU kernel.
+                // The socket in question is about to shut down, so we can just retry the syscall and get
+                // the actual error (usually, but not necessarily, EPIPE).
+                continue
+            #endif
             default:
                 preconditionIsNotUnacceptableErrno(err: err, where: function)
                 throw IOError(errnoCode: err, reason: function)
@@ -356,7 +364,7 @@ internal enum Posix {
     
     @inline(never)
     public static func write(descriptor: CInt, pointer: UnsafeRawPointer, size: Int) throws -> IOResult<Int> {
-        return try syscall(blocking: true) {
+        return try syscall(blocking: true, eprototypeWorkaround: true) {
             sysWrite(descriptor, pointer, size)
         }
     }
@@ -371,7 +379,7 @@ internal enum Posix {
 #if !os(Windows)
     @inline(never)
     public static func writev(descriptor: CInt, iovecs: UnsafeBufferPointer<IOVector>) throws -> IOResult<Int> {
-        return try syscall(blocking: true) {
+        return try syscall(blocking: true, eprototypeWorkaround: true) {
             sysWritev(descriptor, iovecs.baseAddress!, CInt(iovecs.count))
         }
     }
@@ -445,7 +453,7 @@ internal enum Posix {
     public static func sendfile(descriptor: CInt, fd: CInt, offset: off_t, count: size_t) throws -> IOResult<Int> {
         var written: off_t = 0
         do {
-            _ = try syscall(blocking: false) { () -> ssize_t in
+            _ = try syscall(blocking: false, eprototypeWorkaround: true) { () -> ssize_t in
                 #if os(macOS) || os(iOS) || os(watchOS) || os(tvOS)
                     var w: off_t = off_t(count)
                     let result: CInt = Darwin.sendfile(fd, descriptor, offset, &w, nil, 0)
diff --git a/Tests/NIOTests/ChannelTests+XCTest.swift b/Tests/NIOTests/ChannelTests+XCTest.swift
index 1aeb0eeba3b..4da06e45835 100644
--- a/Tests/NIOTests/ChannelTests+XCTest.swift
+++ b/Tests/NIOTests/ChannelTests+XCTest.swift
@@ -84,6 +84,7 @@ extension ChannelTests {
                 ("testFixedSizeRecvByteBufferAllocatorSizeIsConstant", testFixedSizeRecvByteBufferAllocatorSizeIsConstant),
                 ("testCloseInConnectPromise", testCloseInConnectPromise),
                 ("testWritabilityChangeDuringReentrantFlushNow", testWritabilityChangeDuringReentrantFlushNow),
+                ("testTriggerEPROTOTYPE", testTriggerEPROTOTYPE),
            ]
    }
 }
diff --git a/Tests/NIOTests/ChannelTests.swift b/Tests/NIOTests/ChannelTests.swift
index 13d22a4df97..2e2481d679d 100644
--- a/Tests/NIOTests/ChannelTests.swift
+++ b/Tests/NIOTests/ChannelTests.swift
@@ -2814,6 +2814,40 @@ public final class ChannelTests: XCTestCase {
         XCTAssertNoThrow(try handler.becameUnwritable.futureResult.wait())
         XCTAssertNoThrow(try handler.becameWritable.futureResult.wait())
     }
+
+    func testTriggerEPROTOTYPE() throws {
+        // This is a probabilistic test for https://github.com/swift-server/async-http-client/issues/322.
+        // We believe we'll see EPROTOTYPE on write syscalls if we write while the connections are being torn down.
+        // To check this we create 500 connections and close them, while the server attempts to write AS FAST AS IT CAN.
+        // As this test is probabilistic, we must not ignore transient failures in it.
+        let group = MultiThreadedEventLoopGroup(numberOfThreads: 2)
+        defer {
+            XCTAssertNoThrow(try group.syncShutdownGracefully())
+        }
+
+        let serverLoop = group.next()
+        let clientLoop = group.next()
+        XCTAssertFalse(serverLoop === clientLoop)
+
+        let serverFuture = ServerBootstrap(group: serverLoop)
+            .childChannelInitializer { channel in
+                return channel.pipeline.addHandler(AlwaysBeWritingHandler(vectorWrites: [true, false].randomElement()!))
+            }
+            .bind(host: "localhost", port: 0)
+
+        let server: Channel = try assertNoThrowWithValue(try serverFuture.wait())
+        defer {
+            XCTAssertNoThrow(try server.close().wait())
+        }
+
+        let clientFactory = ClientBootstrap(group: clientLoop)
+        let serverAddress = server.localAddress!
+
+        for _ in 0..<500 {
+            let client = try assertNoThrowWithValue(clientFactory.connect(to: serverAddress).wait())
+            XCTAssertNoThrow(try client.close().wait())
+        }
+    }
 }
 
 fileprivate final class FailRegistrationAndDelayCloseHandler: ChannelOutboundHandler {
@@ -2926,3 +2960,49 @@ final class ReentrantWritabilityChangingHandler: ChannelInboundHandler {
         }
     }
 }
+
+final class AlwaysBeWritingHandler: ChannelInboundHandler {
+    typealias InboundIn = ByteBuffer
+    typealias OutboundOut = ByteBuffer
+
+    static let buffer = ByteBuffer(string: "This is some data that I'm sending right now")
+
+    private let doVectorWrite: Bool
+
+    init(vectorWrites: Bool) {
+        self.doVectorWrite = vectorWrites
+    }
+
+    func channelActive(context: ChannelHandlerContext) {
+        self.keepWriting(context: context)
+    }
+
+    func errorCaught(context: ChannelHandlerContext, error: Error) {
+        if let error = error as? IOError, error.errnoCode == EPROTOTYPE {
+            XCTFail("Received EPROTOTYPE error")
+        }
+    }
+
+    private func keepWriting(context: ChannelHandlerContext) {
+        if self.doVectorWrite {
+            context.write(self.wrapOutboundOut(AlwaysBeWritingHandler.buffer)).whenFailure { error in
+                if let error = error as? IOError, error.errnoCode == EPROTOTYPE {
+                    XCTFail("Received EPROTOTYPE error")
+                }
+            }
+        }
+        context.writeAndFlush(self.wrapOutboundOut(AlwaysBeWritingHandler.buffer)).whenComplete { result in
+            switch result {
+            case .success:
+                // We unroll the stack here to avoid blowing it apart.
+                context.eventLoop.execute {
+                    self.keepWriting(context: context)
+                }
+            case .failure(let error):
+                if let error = error as? IOError, error.errnoCode == EPROTOTYPE {
+                    XCTFail("Received EPROTOTYPE error")
+                }
+            }
+        }
+    }
+}