diff --git a/docs/llm.markdown b/docs/llm.markdown
index c4e1e999a..158e0566b 100644
--- a/docs/llm.markdown
+++ b/docs/llm.markdown
@@ -73,9 +73,6 @@ jsonschema llm path/to/schema.json \
   --header "Authorization: Bearer $DOUBLEWORD_API_KEY"
 ```
 
-Doubleword can sometimes be slow to serve a request, independently of the
-model, which is what the generous default `--timeout/-T` leaves room for.
-
 ### OpenAI
 
 ```sh
diff --git a/src/error.h b/src/error.h
index 9d9f061d9..737786d6d 100644
--- a/src/error.h
+++ b/src/error.h
@@ -18,6 +18,7 @@
 #include <sourcemeta/core/options.h>
 #include <sourcemeta/core/yaml.h>
 
+#include <chrono>           // std::chrono::milliseconds
 #include <concepts>         // std::same_as, std::convertible_to
 #include <cstddef>          // std::size_t
 #include <cstdint>          // std::uint64_t
@@ -1326,6 +1327,23 @@ inline auto print_exception(const bool is_json, const Exception &exception)
     }
   }
 
+  // A backend does not report which of its bounds elapsed, so this is the
+  // total that was configured rather than what the request actually took
+  if constexpr (requires(const Exception &current) {
+                  {
+                    current.timeout()
+                  } -> std::same_as<std::chrono::milliseconds>;
+                }) {
+    const auto timeout{exception.timeout()};
+    if (is_json) {
+      error_json.assign(
+          "timeoutMilliseconds",
+          sourcemeta::core::JSON{static_cast<std::size_t>(timeout.count())});
+    } else {
+      std::cerr << "  after " << timeout.count() << " milliseconds\n";
+    }
+  }
+
   if constexpr (requires(const Exception &current) {
                   {
                     current.method()
@@ -2305,6 +2323,15 @@ inline auto try_catch(const sourcemeta::core::Options &options,
     const auto is_json{options.contains("json")};
     print_exception(is_json, error);
     return EXIT_OTHER_INPUT_ERROR;
+  } catch (const sourcemeta::core::HTTPTimeoutError &error) {
+    const auto is_json{options.contains("json")};
+    print_exception(is_json, error);
+    if (!is_json) {
+      std::cerr << "\nPass --timeout/-T with a larger number of seconds to "
+                   "wait longer\n";
+    }
+
+    return EXIT_UNEXPECTED_ERROR;
   } catch (const sourcemeta::core::HTTPStatusError &error) {
     const auto is_json{options.contains("json")};
     print_exception(is_json, error);
diff --git a/test/CMakeLists.txt b/test/CMakeLists.txt
index 17e37c09a..1b331f6e9 100644
--- a/test/CMakeLists.txt
+++ b/test/CMakeLists.txt
@@ -1643,6 +1643,7 @@ add_jsonschema_test_unix_ci(pass_llm_request_response)
 add_jsonschema_test_unix_ci(fail_llm_response_invalid)
 add_jsonschema_test_unix_ci(fail_llm_response_rejected)
 add_jsonschema_test_unix_ci(fail_llm_response_unreadable)
+add_jsonschema_test_unix_ci(fail_llm_timeout)
 add_jsonschema_test_unix_ci(precommit_lint)
 
 if(CMAKE_SYSTEM_NAME STREQUAL "Linux" AND NOT JSONSCHEMA_USE_SYSTEM_CURL)
diff --git a/test/ci/fail_llm_timeout.sh b/test/ci/fail_llm_timeout.sh
new file mode 100755
index 000000000..8b2c38b1c
--- /dev/null
+++ b/test/ci/fail_llm_timeout.sh
@@ -0,0 +1,69 @@
+#!/bin/sh
+
+set -o errexit
+set -o nounset
+
+TMP="$(mktemp -d)"
+PORT=5899
+
+# A server that accepts the connection and never answers, which is the one
+# failure the caller can do something about by waiting longer
+cat << 'EOF' > "$TMP/server.js"
+const http = require('http');
+const server = http.createServer(() => {});
+server.listen(parseInt(process.argv[2], 10));
+EOF
+
+node "$TMP/server.js" "$PORT" &
+SERVER_PID="$!"
+
+clean() {
+  kill "$SERVER_PID" 2>/dev/null || true
+  rm -rf "$TMP"
+}
+trap clean EXIT
+
+sleep 2
+
+cat << 'EOF' > "$TMP/schema.json"
+{
+  "$schema": "https://json-schema.org/draft/2020-12/schema",
+  "type": "string"
+}
+EOF
+
+"$1" llm "$TMP/schema.json" --ask hello \
+  --url "http://localhost:${PORT}/v1/chat/completions" --model my-model \
+  --timeout 2 \
+  > "$TMP/output.txt" 2>&1 && EXIT_CODE="$?" || EXIT_CODE="$?"
+# Unexpected error
+test "$EXIT_CODE" = "1"
+
+cat << EOF > "$TMP/expected.txt"
+error: The HTTP request timed out
+  after 2000 milliseconds
+  with method POST
+  at url http://localhost:${PORT}/v1/chat/completions
+
+Pass --timeout/-T with a larger number of seconds to wait longer
+EOF
+
+diff "$TMP/output.txt" "$TMP/expected.txt"
+
+"$1" llm "$TMP/schema.json" --ask hello \
+  --url "http://localhost:${PORT}/v1/chat/completions" --model my-model \
+  --timeout 2 --json \
+  > "$TMP/output_json.txt" 2>&1 && EXIT_CODE="$?" || EXIT_CODE="$?"
+# Unexpected error
+test "$EXIT_CODE" = "1"
+
+cat << EOF > "$TMP/expected_json.txt"
+{
+  "error": "The HTTP request timed out",
+  "timeoutMilliseconds": 2000,
+  "method": "POST",
+  "url": "http://localhost:${PORT}/v1/chat/completions"
+}
+EOF
+
+diff "$TMP/output_json.txt" "$TMP/expected_json.txt"