diff --git a/Sources/AsyncHTTPClient/ConnectionPool/HTTP1/HTTP1ClientChannelHandler.swift b/Sources/AsyncHTTPClient/ConnectionPool/HTTP1/HTTP1ClientChannelHandler.swift
index affe4770c..ac92e4bc8 100644
--- a/Sources/AsyncHTTPClient/ConnectionPool/HTTP1/HTTP1ClientChannelHandler.swift
+++ b/Sources/AsyncHTTPClient/ConnectionPool/HTTP1/HTTP1ClientChannelHandler.swift
@@ -279,6 +279,7 @@ final class HTTP1ClientChannelHandler: ChannelDuplexHandler {
 
                         oldRequest.succeedRequest(buffer)
                     case .failure(let error):
+                        context.close(promise: nil)
                         oldRequest.fail(error)
                     }
                 }
diff --git a/Tests/AsyncHTTPClientTests/HTTP1ClientChannelHandlerTests+XCTest.swift b/Tests/AsyncHTTPClientTests/HTTP1ClientChannelHandlerTests+XCTest.swift
index 86707520c..66c1a48d1 100644
--- a/Tests/AsyncHTTPClientTests/HTTP1ClientChannelHandlerTests+XCTest.swift
+++ b/Tests/AsyncHTTPClientTests/HTTP1ClientChannelHandlerTests+XCTest.swift
@@ -32,6 +32,7 @@ extension HTTP1ClientChannelHandlerTests {
             ("testIdleReadTimeoutIsCanceledIfRequestIsCanceled", testIdleReadTimeoutIsCanceledIfRequestIsCanceled),
             ("testFailHTTPRequestWithContentLengthBecauseOfChannelInactiveWaitingForDemand", testFailHTTPRequestWithContentLengthBecauseOfChannelInactiveWaitingForDemand),
             ("testWriteHTTPHeadFails", testWriteHTTPHeadFails),
+            ("testHandlerClosesChannelIfLastActionIsSendEndAndItFails", testHandlerClosesChannelIfLastActionIsSendEndAndItFails),
         ]
     }
 }
diff --git a/Tests/AsyncHTTPClientTests/HTTP1ClientChannelHandlerTests.swift b/Tests/AsyncHTTPClientTests/HTTP1ClientChannelHandlerTests.swift
index 4769d2c7e..f97580372 100644
--- a/Tests/AsyncHTTPClientTests/HTTP1ClientChannelHandlerTests.swift
+++ b/Tests/AsyncHTTPClientTests/HTTP1ClientChannelHandlerTests.swift
@@ -457,6 +457,75 @@ class HTTP1ClientChannelHandlerTests: XCTestCase {
             XCTAssertEqual(embedded.isActive, false)
         }
     }
+
+    func testHandlerClosesChannelIfLastActionIsSendEndAndItFails() {
+        let embedded = EmbeddedChannel()
+        let testWriter = TestBackpressureWriter(eventLoop: embedded.eventLoop, parts: 5)
+        var maybeTestUtils: HTTP1TestTools?
+        XCTAssertNoThrow(maybeTestUtils = try embedded.setupHTTP1Connection())
+        guard let testUtils = maybeTestUtils else { return XCTFail("Expected connection setup works") }
+
+        var maybeRequest: HTTPClient.Request?
+        XCTAssertNoThrow(maybeRequest = try HTTPClient.Request(url: "http://localhost/", method: .POST, body: .stream(length: 10) { writer in
+            testWriter.start(writer: writer)
+        }))
+        guard let request = maybeRequest else { return XCTFail("Expected to be able to create a request") }
+
+        let delegate = ResponseAccumulator(request: request)
+        var maybeRequestBag: RequestBag<ResponseAccumulator>?
+        XCTAssertNoThrow(maybeRequestBag = try RequestBag(
+            request: request,
+            eventLoopPreference: .delegate(on: embedded.eventLoop),
+            task: .init(eventLoop: embedded.eventLoop, logger: testUtils.logger),
+            redirectHandler: nil,
+            connectionDeadline: .now() + .seconds(30),
+            requestOptions: .forTests(idleReadTimeout: .milliseconds(200)),
+            delegate: delegate
+        ))
+        guard let requestBag = maybeRequestBag else { return XCTFail("Expected to be able to create a request bag") }
+
+        XCTAssertNoThrow(try embedded.pipeline.addHandler(FailEndHandler(), position: .first).wait())
+
+        // Execute the request and we'll receive the head.
+        testWriter.writabilityChanged(true)
+        testUtils.connection.executeRequest(requestBag)
+        XCTAssertNoThrow(try embedded.receiveHeadAndVerify {
+            XCTAssertEqual($0.method, .POST)
+            XCTAssertEqual($0.uri, "/")
+            XCTAssertEqual($0.headers.first(name: "host"), "localhost")
+            XCTAssertEqual($0.headers.first(name: "content-length"), "10")
+        })
+        // We're going to immediately send the response head and end.
+        let responseHead = HTTPResponseHead(version: .http1_1, status: .ok)
+        XCTAssertNoThrow(try embedded.writeInbound(HTTPClientResponsePart.head(responseHead)))
+        embedded.read()
+
+        // Send the end and confirm the connection is still live.
+        XCTAssertNoThrow(try embedded.writeInbound(HTTPClientResponsePart.end(nil)))
+        XCTAssertEqual(testUtils.connectionDelegate.hitConnectionClosed, 0)
+        XCTAssertEqual(testUtils.connectionDelegate.hitConnectionReleased, 0)
+
+        // Ok, now we can process some reads. We expect 5 reads, but we do _not_ expect an .end, because
+        // the `FailEndHandler` is going to fail it.
+        embedded.embeddedEventLoop.run()
+        XCTAssertEqual(testWriter.written, 5)
+        for _ in 0..<5 {
+            XCTAssertNoThrow(try embedded.receiveBodyAndVerify {
+                XCTAssertEqual($0.readableBytes, 2)
+            })
+        }
+
+        embedded.embeddedEventLoop.run()
+        XCTAssertNil(try embedded.readOutbound(as: HTTPClientRequestPart.self))
+
+        // We should have seen the connection close, and the request is complete.
+        XCTAssertEqual(testUtils.connectionDelegate.hitConnectionClosed, 1)
+        XCTAssertEqual(testUtils.connectionDelegate.hitConnectionReleased, 0)
+
+        XCTAssertThrowsError(try requestBag.task.futureResult.wait()) { error in
+            XCTAssertTrue(error is FailEndHandler.Error)
+        }
+    }
 }
 
 class TestBackpressureWriter {
@@ -636,3 +705,19 @@ class ReadEventHitHandler: ChannelOutboundHandler {
         context.read()
     }
 }
+
+final class FailEndHandler: ChannelOutboundHandler {
+    typealias OutboundIn = HTTPClientRequestPart
+    typealias OutboundOut = HTTPClientRequestPart
+
+    struct Error: Swift.Error {}
+
+    func write(context: ChannelHandlerContext, data: NIOAny, promise: EventLoopPromise<Void>?) {
+        if case .end = self.unwrapOutboundIn(data) {
+            // We fail this.
+            promise?.fail(Self.Error())
+        } else {
+            context.write(data, promise: promise)
+        }
+    }
+}