diff --git a/Sources/AsyncHTTPClient/HTTPHandler.swift b/Sources/AsyncHTTPClient/HTTPHandler.swift
index 2bae67adb..12e6a4fc4 100644
--- a/Sources/AsyncHTTPClient/HTTPHandler.swift
+++ b/Sources/AsyncHTTPClient/HTTPHandler.swift
@@ -814,9 +814,8 @@ extension TaskHandler: ChannelDuplexHandler {
         do {
             try headers.validate(method: request.method, body: request.body)
         } catch {
+            self.errorCaught(context: context, error: error)
             promise?.fail(error)
-            self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
-            self.state = .endOrError
             return
         }
 
@@ -843,9 +842,8 @@ extension TaskHandler: ChannelDuplexHandler {
             self.state = .bodySent
             context.eventLoop.assertInEventLoop()
             if let expectedBodyLength = self.expectedBodyLength, expectedBodyLength != self.actualBodyLength {
-                self.state = .endOrError
                 let error = HTTPClientError.bodyLengthMismatch
-                self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
+                self.errorCaught(context: context, error: error)
                 return context.eventLoop.makeFailedFuture(error)
             }
             return context.writeAndFlush(self.wrapOutboundOut(.end(nil)))
@@ -855,13 +853,7 @@ extension TaskHandler: ChannelDuplexHandler {
             self.callOutToDelegateFireAndForget(self.delegate.didSendRequest)
         }.flatMapErrorThrowing { error in
             context.eventLoop.assertInEventLoop()
-            switch self.state {
-            case .endOrError:
-                break
-            default:
-                self.state = .endOrError
-                self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
-            }
+            self.errorCaught(context: context, error: error)
             throw error
         }.cascade(to: promise)
     }
@@ -906,8 +898,7 @@ extension TaskHandler: ChannelDuplexHandler {
         case .idle:
             if let limit = self.expectedBodyLength, self.actualBodyLength + part.readableBytes > limit {
                 let error = HTTPClientError.bodyLengthMismatch
-                self.state = .endOrError
-                self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
+                self.errorCaught(context: context, error: error)
                 promise.fail(error)
                 return
             }
@@ -915,8 +906,7 @@ extension TaskHandler: ChannelDuplexHandler {
             context.writeAndFlush(self.wrapOutboundOut(.body(part)), promise: promise)
         default:
             let error = HTTPClientError.writeAfterRequestSent
-            self.state = .endOrError
-            self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
+            self.errorCaught(context: context, error: error)
             promise.fail(error)
         }
     }
@@ -983,16 +973,13 @@ extension TaskHandler: ChannelDuplexHandler {
                 context.read()
             }
         case .failure(let error):
-            self.state = .endOrError
-            self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
+            self.errorCaught(context: context, error: error)
         }
     }
 
     func userInboundEventTriggered(context: ChannelHandlerContext, event: Any) {
         if (event as? IdleStateHandler.IdleStateEvent) == .read {
-            self.state = .endOrError
-            let error = HTTPClientError.readTimeout
-            self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
+            self.errorCaught(context: context, error: HTTPClientError.readTimeout)
         } else {
             context.fireUserInboundEventTriggered(event)
         }
@@ -1000,9 +987,7 @@ extension TaskHandler: ChannelDuplexHandler {
 
     func triggerUserOutboundEvent(context: ChannelHandlerContext, event: Any, promise: EventLoopPromise<Void>?) {
         if (event as? TaskCancelEvent) != nil {
-            self.state = .endOrError
-            let error = HTTPClientError.cancelled
-            self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
+            self.errorCaught(context: context, error: HTTPClientError.cancelled)
             promise?.succeed(())
         } else {
             context.triggerUserOutboundEvent(event, promise: promise)
@@ -1014,9 +999,7 @@ extension TaskHandler: ChannelDuplexHandler {
         case .endOrError:
             break
         case .body, .head, .idle, .redirected, .sent, .bodySent:
-            self.state = .endOrError
-            let error = HTTPClientError.remoteConnectionClosed
-            self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
+            self.errorCaught(context: context, error: HTTPClientError.remoteConnectionClosed)
         }
         context.fireChannelInactive()
     }
@@ -1038,14 +1021,20 @@ extension TaskHandler: ChannelDuplexHandler {
                 self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
             }
         default:
-            self.state = .endOrError
-            self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
+            switch self.state {
+            case .idle, .bodySent, .sent, .head, .redirected, .body:
+                self.state = .endOrError
+                self.failTaskAndNotifyDelegate(error: error, self.delegate.didReceiveError)
+            case .endOrError:
+                // error was already handled
+                break
+            }
         }
     }
 
     func handlerAdded(context: ChannelHandlerContext) {
         guard context.channel.isActive else {
-            self.failTaskAndNotifyDelegate(error: HTTPClientError.remoteConnectionClosed, self.delegate.didReceiveError)
+            self.errorCaught(context: context, error: HTTPClientError.remoteConnectionClosed)
             return
         }
     }
diff --git a/Tests/AsyncHTTPClientTests/HTTPClientInternalTests+XCTest.swift b/Tests/AsyncHTTPClientTests/HTTPClientInternalTests+XCTest.swift
index 6177127d0..648eb8078 100644
--- a/Tests/AsyncHTTPClientTests/HTTPClientInternalTests+XCTest.swift
+++ b/Tests/AsyncHTTPClientTests/HTTPClientInternalTests+XCTest.swift
@@ -46,6 +46,7 @@ extension HTTPClientInternalTests {
             ("testConnectErrorCalloutOnCorrectEL", testConnectErrorCalloutOnCorrectEL),
             ("testInternalRequestURI", testInternalRequestURI),
             ("testBodyPartStreamStateChangedBeforeNotification", testBodyPartStreamStateChangedBeforeNotification),
+            ("testHandlerDoubleError", testHandlerDoubleError),
         ]
     }
 }
diff --git a/Tests/AsyncHTTPClientTests/HTTPClientInternalTests.swift b/Tests/AsyncHTTPClientTests/HTTPClientInternalTests.swift
index 52348ba94..706a3bbd7 100644
--- a/Tests/AsyncHTTPClientTests/HTTPClientInternalTests.swift
+++ b/Tests/AsyncHTTPClientTests/HTTPClientInternalTests.swift
@@ -1080,4 +1080,43 @@ class HTTPClientInternalTests: XCTestCase {
         XCTAssertNoThrow(try channel.readOutbound(as: HTTPClientRequestPart.self)) // .head
         XCTAssertNoThrow(XCTAssertTrue(try channel.finish().isClean))
     }
+
+    func testHandlerDoubleError() throws {
+        class ErrorCountingDelegate: HTTPClientResponseDelegate {
+            typealias Response = Void
+
+            var count = 0
+
+            func didReceiveError(task: HTTPClient.Task<Response>, _: Error) {
+                self.count += 1
+            }
+
+            func didFinishRequest(task: HTTPClient.Task<Void>) throws {
+                return ()
+            }
+        }
+
+        class SendTwoErrorsHandler: ChannelInboundHandler {
+            typealias InboundIn = Any
+
+            func handlerAdded(context: ChannelHandlerContext) {
+                context.fireErrorCaught(HTTPClientError.cancelled)
+                context.fireErrorCaught(HTTPClientError.cancelled)
+            }
+        }
+
+        let channel = EmbeddedChannel()
+        let task = Task<Void>(eventLoop: channel.eventLoop, logger: HTTPClient.loggingDisabled)
+        let delegate = ErrorCountingDelegate()
+        try channel.pipeline.addHandler(TaskHandler(task: task,
+                                                    kind: .host,
+                                                    delegate: delegate,
+                                                    redirectHandler: nil,
+                                                    ignoreUncleanSSLShutdown: false,
+                                                    logger: HTTPClient.loggingDisabled)).wait()
+
+        try channel.pipeline.addHandler(SendTwoErrorsHandler()).wait()
+
+        XCTAssertEqual(delegate.count, 1)
+    }
 }
diff --git a/Tests/AsyncHTTPClientTests/HTTPClientTests+XCTest.swift b/Tests/AsyncHTTPClientTests/HTTPClientTests+XCTest.swift
index eb4dd7cb5..918da82ac 100644
--- a/Tests/AsyncHTTPClientTests/HTTPClientTests+XCTest.swift
+++ b/Tests/AsyncHTTPClientTests/HTTPClientTests+XCTest.swift
@@ -122,6 +122,7 @@ extension HTTPClientTests {
             ("testContentLengthTooShortFails", testContentLengthTooShortFails),
             ("testBodyUploadAfterEndFails", testBodyUploadAfterEndFails),
             ("testNoBytesSentOverBodyLimit", testNoBytesSentOverBodyLimit),
+            ("testDoubleError", testDoubleError),
         ]
     }
 }
diff --git a/Tests/AsyncHTTPClientTests/HTTPClientTests.swift b/Tests/AsyncHTTPClientTests/HTTPClientTests.swift
index 04287ef0d..970ab7dbe 100644
--- a/Tests/AsyncHTTPClientTests/HTTPClientTests.swift
+++ b/Tests/AsyncHTTPClientTests/HTTPClientTests.swift
@@ -2602,4 +2602,29 @@ class HTTPClientTests: XCTestCase {
 
         XCTAssertThrowsError(try future.wait())
     }
+
+    func testDoubleError() throws {
+        // This is needed to that connection pool will not get into closed state when we release
+        // second connection.
+        _ = self.defaultClient.get(url: "http://localhost:\(self.defaultHTTPBin.port)/events/10/1")
+
+        var request = try HTTPClient.Request(url: "http://localhost:\(self.defaultHTTPBin.port)/wait", method: .POST)
+        request.body = .stream { writer in
+            // Start writing chunks so tha we will try to write after read timeout is thrown
+            for _ in 1...10 {
+                _ = writer.write(.byteBuffer(ByteBuffer(string: "1234")))
+            }
+
+            let promise = self.clientGroup.next().makePromise(of: Void.self)
+            self.clientGroup.next().scheduleTask(in: .milliseconds(3)) {
+                writer.write(.byteBuffer(ByteBuffer(string: "1234"))).cascade(to: promise)
+            }
+
+            return promise.futureResult
+        }
+
+        // We specify a deadline of 2 ms co that request will be timed out before all chunks are writtent,
+        // we need to verify that second error on write after timeout does not lead to double-release.
+        XCTAssertThrowsError(try self.defaultClient.execute(request: request, deadline: .now() + .milliseconds(2)).wait())
+    }
 }