diff --git a/doc/modules/ROOT/nav.adoc b/doc/modules/ROOT/nav.adoc
index be90d837..7c10e4ae 100644
--- a/doc/modules/ROOT/nav.adoc
+++ b/doc/modules/ROOT/nav.adoc
@@ -1,5 +1,6 @@
 * xref:index.adoc[Introduction]
 * xref:requests_responses.adoc[]
+* xref:cancellation.adoc[]
 * xref:serialization.adoc[]
 * xref:logging.adoc[]
 * xref:benchmarks.adoc[]
diff --git a/doc/modules/ROOT/pages/cancellation.adoc b/doc/modules/ROOT/pages/cancellation.adoc
new file mode 100644
index 00000000..ed224de3
--- /dev/null
+++ b/doc/modules/ROOT/pages/cancellation.adoc
@@ -0,0 +1,57 @@
+//
+// Copyright (c) 2025 Marcelo Zimbres Silva (mzimbres@gmail.com),
+// Ruben Perez Hidalgo (rubenperez038 at gmail dot com)
+//
+// Distributed under the Boost Software License, Version 1.0. (See accompanying
+// file LICENSE_1_0.txt or copy at http://www.boost.org/LICENSE_1_0.txt)
+//
+
+= Cancellation
+
+Requests may take a very long time. If the server is down, they may suspend forever,
+waiting for the server to be up. Fortunately, requests can be cancelled after
+a certain time using asio::cancel_after:
+
+```
+request req;
+// ...
+
+co_await conn.async_exec(req, resp, asio::cancel_after(10s));
+```
+
+If the request hasn't been responded after 10 seconds, it will
+fail with `asio::error::operation_aborted`. With the coroutine
+usage above, this means a `boost::system::system_error` exception
+with the error code mentioned above.
+
+== Retrying idempotent requests
+
+By default, the library waits until the server is up,
+and then sends the request. But what happens if there is a communication
+error after sending the request, but before receiving a response?
+
+In this situation, we don't know if the request was processed by the server or not.
+And we have no way to know it. By default, the library mark these requests as
+failed with `asio::error::operation_aborted`. (TODO: do we want another error code here?).
+
+Some requests can be executed several times and result in the same outcome
+as executing them only once. We say that these requests are idempotent.
+The `SET` command is idempotent, while `INCR` is not.
+
+If you know that a request contains only idempotent commands,
+you can instruct Redis to retry the request on failure, even
+if the library is unsure about whether the server received the request or not.
+You can do so by setting request::config::cancel_if_unresponded to false:
+
+```
+request req;
+req.push("SET", "my_key", 42); // idempotent
+req.get_config().cancel_on_connection_lost = false; // TODO: we shouldn't need this
+req.get_config().cancel_if_unresponded = false; // retry
+
+// Makes sure that the key is set, even in the presence of network errors.
+// Note that if the server is down, the current coroutine will remain suspended
+// until the server is capable of serving requests again (e.g. until a process manager restarts the server).
+// Use cancel_after as seen above if you need to limit this time.
+co_await conn.async_exec(req, ignore);
+```
diff --git a/doc/modules/ROOT/pages/index.adoc b/doc/modules/ROOT/pages/index.adoc
index 6d87beb7..fe9f04f1 100644
--- a/doc/modules/ROOT/pages/index.adoc
+++ b/doc/modules/ROOT/pages/index.adoc
@@ -139,6 +139,7 @@ receiver(std::shared_ptr<connection> conn) -> net::awaitable<void>
 
 Here is a list of topics that you might be interested in:
 
+* xref:cancellation.adoc[Setting timeouts to requests and managing cancellation].
 * xref:requests_responses.adoc[More on requests and responses].
 * xref:serialization.adoc[Serializing and parsing into custom types].
 * xref:logging.adoc[Configuring logging].
diff --git a/example/CMakeLists.txt b/example/CMakeLists.txt
index 8f8bdd04..c9b18235 100644
--- a/example/CMakeLists.txt
+++ b/example/CMakeLists.txt
@@ -27,6 +27,7 @@ make_testable_example(cpp20_intro 20)
 make_testable_example(cpp20_containers 20)
 make_testable_example(cpp20_json 20)
 make_testable_example(cpp20_unix_sockets 20)
+make_testable_example(cpp20_timeouts 20)
 
 make_example(cpp20_subscriber 20)
 make_example(cpp20_streams 20)
diff --git a/example/cpp20_timeouts.cpp b/example/cpp20_timeouts.cpp
new file mode 100644
index 00000000..98168339
--- /dev/null
+++ b/example/cpp20_timeouts.cpp
@@ -0,0 +1,49 @@
+/* Copyright (c) 2018-2022 Marcelo Zimbres Silva (mzimbres@gmail.com)
+ *
+ * Distributed under the Boost Software License, Version 1.0. (See
+ * accompanying file LICENSE.txt)
+ */
+
+#include <boost/redis/connection.hpp>
+
+#include <boost/asio/cancel_after.hpp>
+#include <boost/asio/co_spawn.hpp>
+#include <boost/asio/consign.hpp>
+#include <boost/asio/detached.hpp>
+
+#include <iostream>
+
+#if defined(BOOST_ASIO_HAS_CO_AWAIT)
+
+namespace asio = boost::asio;
+using boost::redis::request;
+using boost::redis::response;
+using boost::redis::config;
+using boost::redis::connection;
+using namespace std::chrono_literals;
+
+// Called from the main function (see main.cpp)
+auto co_main(config cfg) -> asio::awaitable<void>
+{
+   auto conn = std::make_shared<connection>(co_await asio::this_coro::executor);
+   conn->async_run(cfg, asio::consign(asio::detached, conn));
+
+   // A request containing only a ping command.
+   request req;
+   req.push("PING", "Hello world");
+
+   // Response where the PONG response will be stored.
+   response<std::string> resp;
+
+   // Executes the request with a timeout. If the server is down,
+   // async_exec will wait until it's back again, so it,
+   // may suspend for a long time.
+   // For this reason, it's good practice to set a timeout to requests with cancel_after.
+   // If the request hasn't completed after 10 seconds, an exception will be thrown.
+   co_await conn->async_exec(req, resp, asio::cancel_after(10s));
+   conn->cancel();
+
+   std::cout << "PING: " << std::get<0>(resp).value() << std::endl;
+}
+
+#endif  // defined(BOOST_ASIO_HAS_CO_AWAIT)
diff --git a/include/boost/redis/connection.hpp b/include/boost/redis/connection.hpp
index 5695166d..ad976557 100644
--- a/include/boost/redis/connection.hpp
+++ b/include/boost/redis/connection.hpp
@@ -789,26 +789,10 @@ class basic_connection {
    template <class CompletionToken = asio::default_completion_token_t<executor_type>>
    auto async_run(config const& cfg, CompletionToken&& token = {})
    {
-      impl_->cfg_ = cfg;
-      impl_->mpx_.set_config(cfg);
-
-      // If the token's slot has cancellation enabled, it should just emit
-      // the cancellation signal in our connection. This lets us unify the cancel()
-      // function and per-operation cancellation
-      auto slot = asio::get_associated_cancellation_slot(token);
-      if (slot.is_connected()) {
-         slot.template emplace<detail::run_cancel_handler<Executor>>(*impl_);
-      }
-
-      // Overwrite the token's cancellation slot: the composed operation
-      // should use the signal's slot so we can generate cancellations in cancel()
-      auto token_with_slot = asio::bind_cancellation_slot(
-         impl_->run_signal_.slot(),
-         std::forward<CompletionToken>(token));
-      return asio::async_compose<decltype(token_with_slot), void(system::error_code)>(
-         detail::run_op<Executor>{impl_.get()},
-         token_with_slot,
-         impl_->writer_timer_);
+      return asio::async_initiate<CompletionToken, void(system::error_code)>(
+         run_initiation{impl_.get()},
+         token,
+         &cfg);
    }
 
    /**
@@ -1133,6 +1117,42 @@ class basic_connection {
       impl_->logger_.reset(detail::make_stderr_logger(lvl, cfg.log_prefix));
    }
 
+   // Initiation for async_run. This is required because we need access
+   // to the final handler (rather than the completion token) within the initiation,
+   // to modify the handler's cancellation slot.
+   struct run_initiation {
+      detail::connection_impl<Executor>* self;
+
+      using executor_type = Executor;
+      executor_type get_executor() const noexcept { return self->get_executor(); }
+
+      template <class Handler>
+      void operator()(Handler&& handler, config const* cfg)
+      {
+         self->cfg_ = *cfg;
+         self->mpx_.set_config(*cfg);
+
+         // If the token's slot has cancellation enabled, it should just emit
+         // the cancellation signal in our connection. This lets us unify the cancel()
+         // function and per-operation cancellation
+         auto slot = asio::get_associated_cancellation_slot(handler);
+         if (slot.is_connected()) {
+            slot.template emplace<detail::run_cancel_handler<Executor>>(*self);
+         }
+
+         // Overwrite the token's cancellation slot: the composed operation
+         // should use the signal's slot so we can generate cancellations in cancel()
+         auto token_with_slot = asio::bind_cancellation_slot(
+            self->run_signal_.slot(),
+            std::forward<Handler>(handler));
+
+         asio::async_compose<decltype(token_with_slot), void(system::error_code)>(
+            detail::run_op<Executor>{self},
+            token_with_slot,
+            self->writer_timer_);
+      }
+   };
+
    friend class connection;
 
    std::unique_ptr<detail::connection_impl<Executor>> impl_;
@@ -1224,11 +1244,8 @@ class connection {
    auto async_run(config const& cfg, CompletionToken&& token = {})
    {
       return asio::async_initiate<CompletionToken, void(boost::system::error_code)>(
-         [](auto handler, connection* self, config const* cfg) {
-            self->async_run_impl(*cfg, std::move(handler));
-         },
+         initiation{this},
          token,
-         this,
          &cfg);
    }
 
@@ -1256,11 +1273,8 @@ class connection {
    auto async_run(config const& cfg, logger l, CompletionToken&& token = {})
    {
       return asio::async_initiate<CompletionToken, void(boost::system::error_code)>(
-         [](auto handler, connection* self, config const* cfg, logger l) {
-            self->async_run_impl(*cfg, std::move(l), std::move(handler));
-         },
+         initiation{this},
          token,
-         this,
          &cfg,
          std::move(l));
    }
@@ -1299,11 +1313,8 @@ class connection {
    auto async_exec(request const& req, any_adapter adapter, CompletionToken&& token = {})
    {
       return asio::async_initiate<CompletionToken, void(boost::system::error_code, std::size_t)>(
-         [](auto handler, connection* self, request const* req, any_adapter&& adapter) {
-            self->async_exec_impl(*req, std::move(adapter), std::move(handler));
-         },
+         initiation{this},
          token,
-         this,
          &req,
          std::move(adapter));
    }
@@ -1358,6 +1369,34 @@ class connection {
    }
 
 private:
+   // Function object to initiate the async ops that use asio::any_completion_handler.
+   // Required for asio::cancel_after to work.
+   // Since all ops have different arguments, a single struct with different overloads is enough.
+   struct initiation {
+      connection* self;
+
+      using executor_type = asio::any_io_executor;
+      executor_type get_executor() const noexcept { return self->get_executor(); }
+
+      template <class Handler>
+      void operator()(Handler&& handler, config const* cfg, logger l)
+      {
+         self->async_run_impl(*cfg, std::move(l), std::forward<Handler>(handler));
+      }
+
+      template <class Handler>
+      void operator()(Handler&& handler, config const* cfg)
+      {
+         self->async_run_impl(*cfg, std::forward<Handler>(handler));
+      }
+
+      template <class Handler>
+      void operator()(Handler&& handler, request const* req, any_adapter&& adapter)
+      {
+         self->async_exec_impl(*req, std::move(adapter), std::forward<Handler>(handler));
+      }
+   };
+
    void async_run_impl(
       config const& cfg,
       logger&& l,
diff --git a/test/CMakeLists.txt b/test/CMakeLists.txt
index d21279f3..01b49824 100644
--- a/test/CMakeLists.txt
+++ b/test/CMakeLists.txt
@@ -64,6 +64,7 @@ make_test(test_issue_50)
 make_test(test_conversions)
 make_test(test_conn_tls)
 make_test(test_unix_sockets)
+make_test(test_conn_cancel_after)
 
 # Coverage
 set(
diff --git a/test/test_conn_cancel_after.cpp b/test/test_conn_cancel_after.cpp
new file mode 100644
index 00000000..dd25a4a5
--- /dev/null
+++ b/test/test_conn_cancel_after.cpp
@@ -0,0 +1,110 @@
+//
+// Copyright (c) 2025 Marcelo Zimbres Silva (mzimbres@gmail.com),
+// Ruben Perez Hidalgo (rubenperez038 at gmail dot com)
+//
+// Distributed under the Boost Software License, Version 1.0. (See accompanying
+// file LICENSE_1_0.txt or copy at http://www.boost.org/LICENSE_1_0.txt)
+//
+
+#include <boost/redis/connection.hpp>
+#include <boost/redis/ignore.hpp>
+#include <boost/redis/request.hpp>
+#include <boost/redis/response.hpp>
+
+#include <boost/asio/cancel_after.hpp>
+#include <boost/asio/error.hpp>
+#include <boost/asio/experimental/channel_error.hpp>
+#include <boost/asio/io_context.hpp>
+#include <boost/core/lightweight_test.hpp>
+
+#include "common.hpp"
+
+using namespace std::chrono_literals;
+namespace asio = boost::asio;
+using boost::system::error_code;
+using boost::redis::request;
+using boost::redis::basic_connection;
+using boost::redis::connection;
+using boost::redis::ignore;
+using boost::redis::generic_response;
+
+namespace {
+
+template <class Connection>
+void test_run()
+{
+   // Setup
+   asio::io_context ioc;
+   Connection conn{ioc};
+   bool run_finished = false;
+
+   // Call the function with a very short timeout
+   conn.async_run(make_test_config(), asio::cancel_after(1ms, [&](error_code ec) {
+                     BOOST_TEST_EQ(ec, asio::error::operation_aborted);
+                     run_finished = true;
+                  }));
+
+   ioc.run_for(test_timeout);
+
+   BOOST_TEST(run_finished);
+}
+
+template <class Connection>
+void test_exec()
+{
+   // Setup
+   asio::io_context ioc;
+   Connection conn{ioc};
+   bool exec_finished = false;
+
+   request req;
+   req.push("PING", "cancel_after");
+
+   // Call the function with a very short timeout.
+   // The connection is not being run, so these can't succeed
+   conn.async_exec(req, ignore, asio::cancel_after(1ms, [&](error_code ec, std::size_t) {
+                      BOOST_TEST_EQ(ec, asio::error::operation_aborted);
+                      exec_finished = true;
+                   }));
+
+   ioc.run_for(test_timeout);
+
+   BOOST_TEST(exec_finished);
+}
+
+template <class Connection>
+void test_receive()
+{
+   // Setup
+   asio::io_context ioc;
+   Connection conn{ioc};
+   bool receive_finished = false;
+   generic_response resp;
+   conn.set_receive_response(resp);
+
+   // Call the function with a very short timeout.
+   conn.async_receive(asio::cancel_after(1ms, [&](error_code ec, std::size_t) {
+      BOOST_TEST_EQ(ec, asio::experimental::channel_errc::channel_cancelled);
+      receive_finished = true;
+   }));
+
+   ioc.run_for(test_timeout);
+
+   BOOST_TEST(receive_finished);
+}
+
+}  // namespace
+
+int main()
+{
+   test_run<basic_connection<asio::io_context::executor_type>>();
+   test_run<connection>();
+
+   test_exec<basic_connection<asio::io_context::executor_type>>();
+   test_exec<connection>();
+
+   test_receive<basic_connection<asio::io_context::executor_type>>();
+   test_receive<connection>();
+
+   return boost::report_errors();
+}
diff --git a/test/test_conn_run_cancel.cpp b/test/test_conn_run_cancel.cpp
index 769709c4..053c58f5 100644
--- a/test/test_conn_run_cancel.cpp
+++ b/test/test_conn_run_cancel.cpp
@@ -12,6 +12,7 @@
 #include <boost/asio/bind_cancellation_slot.hpp>
 #include <boost/asio/cancellation_signal.hpp>
 #include <boost/asio/cancellation_type.hpp>
+#include <boost/asio/io_context.hpp>
 #include <boost/core/lightweight_test.hpp>
 
 #include "common.hpp"
@@ -27,13 +28,14 @@ using namespace boost::redis;
 namespace {
 
 // Terminal and partial cancellation work for async_run
+template <class Connection>
 void test_per_operation_cancellation(std::string_view name, net::cancellation_type_t cancel_type)
 {
    std::cerr << "Running test case: " << name << std::endl;
 
    // Setup
    net::io_context ioc;
-   connection conn{ioc};
+   Connection conn{ioc};
    net::cancellation_signal sig;
 
    request req;
@@ -66,8 +68,21 @@ void test_per_operation_cancellation(std::string_view name, net::cancellation_ty
 
 int main()
 {
-   test_per_operation_cancellation("terminal", net::cancellation_type_t::terminal);
-   test_per_operation_cancellation("partial", net::cancellation_type_t::partial);
+   using basic_connection_t = basic_connection<net::io_context::executor_type>;
+
+   test_per_operation_cancellation<basic_connection_t>(
+      "basic_connection, terminal",
+      net::cancellation_type_t::terminal);
+   test_per_operation_cancellation<basic_connection_t>(
+      "basic_connection, partial",
+      net::cancellation_type_t::partial);
+
+   test_per_operation_cancellation<connection>(
+      "connection, terminal",
+      net::cancellation_type_t::terminal);
+   test_per_operation_cancellation<connection>(
+      "connection, partial",
+      net::cancellation_type_t::partial);
 
    return boost::report_errors();
 }