diff --git a/core/src/main/java/com/linecorp/armeria/client/HttpChannelPool.java b/core/src/main/java/com/linecorp/armeria/client/HttpChannelPool.java
index d88fa5b3f09..cd67ebc63a3 100644
--- a/core/src/main/java/com/linecorp/armeria/client/HttpChannelPool.java
+++ b/core/src/main/java/com/linecorp/armeria/client/HttpChannelPool.java
@@ -847,7 +847,11 @@ private void handlePiggyback(SessionProtocol desiredProtocol,
                     break;
                 case NEW_CONNECTION:
                     timingsBuilder.pendingAcquisitionEnd();
-                    connect(desiredProtocol, serializationFormat, key, childPromise, timingsBuilder);
+                    // Reschedule the connection attempt to avoid creating a new connection in the middle of
+                    // initializing the acquired channel.
+                    eventLoop.execute(() -> {
+                        connect(desiredProtocol, serializationFormat, key, childPromise, timingsBuilder);
+                    });
                     break;
                 case PIGGYBACKED_AGAIN:
                     // There's nothing to do because usePendingAcquisition() was called successfully above.
diff --git a/core/src/test/java/com/linecorp/armeria/client/Http1ClientClosedSessionExceptionTest.java b/core/src/test/java/com/linecorp/armeria/client/Http1ClientClosedSessionExceptionTest.java
new file mode 100644
index 00000000000..2eaa4c330b5
--- /dev/null
+++ b/core/src/test/java/com/linecorp/armeria/client/Http1ClientClosedSessionExceptionTest.java
@@ -0,0 +1,116 @@
+/*
+ * Copyright 2025 LINE Corporation
+ *
+ * LINE Corporation licenses this file to you under the Apache License,
+ * version 2.0 (the "License"); you may not use this file except in compliance
+ * with the License. You may obtain a copy of the License at:
+ *
+ *   https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS, WITHOUT
+ * WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. See the
+ * License for the specific language governing permissions and limitations
+ * under the License.
+ *
+ */
+
+package com.linecorp.armeria.client;
+
+import java.net.InetSocketAddress;
+import java.util.concurrent.CompletableFuture;
+import java.util.concurrent.atomic.AtomicReference;
+
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.RegisterExtension;
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
+
+import com.linecorp.armeria.common.AggregatedHttpResponse;
+import com.linecorp.armeria.common.CommonPools;
+import com.linecorp.armeria.common.HttpHeaderNames;
+import com.linecorp.armeria.common.SessionProtocol;
+import com.linecorp.armeria.common.logging.RequestLog;
+import com.linecorp.armeria.internal.testing.NettyServerExtension;
+
+import io.netty.channel.Channel;
+import io.netty.channel.ChannelDuplexHandler;
+import io.netty.channel.ChannelFutureListener;
+import io.netty.channel.ChannelHandlerContext;
+import io.netty.handler.codec.http.DefaultFullHttpResponse;
+import io.netty.handler.codec.http.FullHttpRequest;
+import io.netty.handler.codec.http.HttpObjectAggregator;
+import io.netty.handler.codec.http.HttpResponse;
+import io.netty.handler.codec.http.HttpResponseStatus;
+import io.netty.handler.codec.http.HttpServerCodec;
+import io.netty.handler.codec.http.HttpVersion;
+
+class Http1ClientClosedSessionExceptionTest {
+
+    private static final Logger logger = LoggerFactory.getLogger(Http1ClientClosedSessionExceptionTest.class);
+
+    @RegisterExtension
+    static NettyServerExtension http1Server = new NettyServerExtension() {
+        @Override
+        protected void configure(Channel ch) throws Exception {
+            ch.pipeline().addLast(new HttpServerCodec());
+            ch.pipeline().addLast(new HttpObjectAggregator(1024));
+            ch.pipeline().addLast(new ChannelDuplexHandler() {
+                @Override
+                public void channelRead(ChannelHandlerContext ctx, Object msg) throws Exception {
+                    if (msg instanceof FullHttpRequest) {
+                        final HttpResponse response = new DefaultFullHttpResponse(
+                                HttpVersion.HTTP_1_1, HttpResponseStatus.OK);
+                        // Make sure the connection is closed after the response is sent.
+                        response.headers().add(HttpHeaderNames.CONNECTION, "close");
+                        ctx.writeAndFlush(response)
+                           .addListener(ChannelFutureListener.CLOSE);
+                    } else {
+                        ctx.fireChannelRead(msg);
+                    }
+                }
+            });
+        }
+    };
+
+    @Test
+    void shouldSendHttp1RequestConcurrently() throws Throwable {
+        final WebClient client = WebClient.of(SessionProtocol.HTTP, http1Server.endpoint());
+
+        SessionProtocolNegotiationCache.setUnsupported(
+                new InetSocketAddress("127.0.0.1", http1Server.address().getPort()),
+                SessionProtocol.H2C);
+        final AtomicReference<Throwable> failed = new AtomicReference<>();
+        final Runnable loader = () -> {
+            while (failed.get() == null) {
+                try (ClientRequestContextCaptor captor = Clients.newContextCaptor()) {
+                    try {
+                        final CompletableFuture<AggregatedHttpResponse> future = client.get("/").aggregate();
+                        final ClientRequestContext ctx = captor.get();
+                        future.join();
+                        final RequestLog log = ctx.log().whenComplete().join();
+                        final Throwable responseCause = log.responseCause();
+                        if (responseCause != null) {
+                            failed.set(responseCause);
+                        }
+                    } catch (Throwable ex) {
+                        failed.set(new RuntimeException("Failed to receive the response. ctx: " + captor.get(),
+                                                        ex));
+                    }
+                }
+            }
+        };
+
+        for (int i = 0; i < 5; i++) {
+            CommonPools.blockingTaskExecutor().execute(loader);
+        }
+
+        for (int i = 0; i < 5; i++) {
+            Thread.sleep(1000);
+            if (failed.get() != null) {
+                throw failed.get();
+            }
+        }
+        logger.info("All requests completed successfully");
+    }
+}