diff --git a/modules/caddyhttp/metrics.go b/modules/caddyhttp/metrics.go
index 9c0f961e5..111389218 100644
--- a/modules/caddyhttp/metrics.go
+++ b/modules/caddyhttp/metrics.go
@@ -2,6 +2,7 @@ package caddyhttp
 
 import (
 	"context"
+	"errors"
 	"net/http"
 	"sync"
 	"time"
@@ -137,22 +138,33 @@ func (h *metricsInstrumentedHandler) ServeHTTP(w http.ResponseWriter, r *http.Re
 	err := h.mh.ServeHTTP(wrec, r, next)
 	dur := time.Since(start).Seconds()
 	httpMetrics.requestCount.With(labels).Inc()
+
+	observeRequest := func(status int) {
+		// If the code hasn't been set yet, and we didn't encounter an error, we're
+		// probably falling through with an empty handler.
+		if statusLabels["code"] == "" {
+			// we still sanitize it, even though it's likely to be 0. A 200 is
+			// returned on fallthrough so we want to reflect that.
+			statusLabels["code"] = metrics.SanitizeCode(status)
+		}
+
+		httpMetrics.requestDuration.With(statusLabels).Observe(dur)
+		httpMetrics.requestSize.With(statusLabels).Observe(float64(computeApproximateRequestSize(r)))
+		httpMetrics.responseSize.With(statusLabels).Observe(float64(wrec.Size()))
+	}
+
 	if err != nil {
+		var handlerErr HandlerError
+		if errors.As(err, &handlerErr) {
+			observeRequest(handlerErr.StatusCode)
+		}
+
 		httpMetrics.requestErrors.With(labels).Inc()
+
 		return err
 	}
 
-	// If the code hasn't been set yet, and we didn't encounter an error, we're
-	// probably falling through with an empty handler.
-	if statusLabels["code"] == "" {
-		// we still sanitize it, even though it's likely to be 0. A 200 is
-		// returned on fallthrough so we want to reflect that.
-		statusLabels["code"] = metrics.SanitizeCode(wrec.Status())
-	}
-
-	httpMetrics.requestDuration.With(statusLabels).Observe(dur)
-	httpMetrics.requestSize.With(statusLabels).Observe(float64(computeApproximateRequestSize(r)))
-	httpMetrics.responseSize.With(statusLabels).Observe(float64(wrec.Size()))
+	observeRequest(wrec.Status())
 
 	return nil
 }
diff --git a/modules/caddyhttp/metrics_test.go b/modules/caddyhttp/metrics_test.go
index 6311935ae..8f88549d5 100644
--- a/modules/caddyhttp/metrics_test.go
+++ b/modules/caddyhttp/metrics_test.go
@@ -5,8 +5,10 @@ import (
 	"errors"
 	"net/http"
 	"net/http/httptest"
+	"strings"
 	"testing"
 
+	"github.com/prometheus/client_golang/prometheus"
 	"github.com/prometheus/client_golang/prometheus/testutil"
 )
 
@@ -75,6 +77,123 @@ func TestMetricsInstrumentedHandler(t *testing.T) {
 	if actual := w.Result().Header; len(actual) != 0 {
 		t.Errorf("Not empty: expected headers to be empty, but got %#v", actual)
 	}
+
+	// handler returning an error with an HTTP status
+	mh = middlewareHandlerFunc(func(w http.ResponseWriter, r *http.Request, h Handler) error {
+		return Error(http.StatusTooManyRequests, nil)
+	})
+
+	ih = newMetricsInstrumentedHandler("foo", mh)
+
+	r = httptest.NewRequest("GET", "/", nil)
+	w = httptest.NewRecorder()
+
+	if err := ih.ServeHTTP(w, r, nil); err == nil {
+		t.Errorf("expected error to be propagated")
+	}
+
+	expected := `
+	# HELP caddy_http_request_duration_seconds Histogram of round-trip request durations.
+	# TYPE caddy_http_request_duration_seconds histogram
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="0.005"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="0.01"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="0.025"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="0.05"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="0.1"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="0.25"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="0.5"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="1"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="2.5"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="5"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="10"} 1
+	caddy_http_request_duration_seconds_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="+Inf"} 1
+	caddy_http_request_duration_seconds_count{code="429",handler="foo",method="GET",server="UNKNOWN"} 1
+	# HELP caddy_http_request_size_bytes Total size of the request. Includes body
+	# TYPE caddy_http_request_size_bytes histogram
+	caddy_http_request_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="256"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="1024"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="4096"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="16384"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="65536"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="262144"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="1.048576e+06"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="4.194304e+06"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="+Inf"} 1
+    caddy_http_request_size_bytes_sum{code="200",handler="bar",method="GET",server="UNKNOWN"} 23
+    caddy_http_request_size_bytes_count{code="200",handler="bar",method="GET",server="UNKNOWN"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="256"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="1024"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="4096"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="16384"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="65536"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="262144"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="1.048576e+06"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="4.194304e+06"} 1
+    caddy_http_request_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="+Inf"} 1
+    caddy_http_request_size_bytes_sum{code="200",handler="empty",method="GET",server="UNKNOWN"} 23
+    caddy_http_request_size_bytes_count{code="200",handler="empty",method="GET",server="UNKNOWN"} 1
+	caddy_http_request_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="256"} 1
+	caddy_http_request_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="1024"} 1
+	caddy_http_request_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="4096"} 1
+	caddy_http_request_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="16384"} 1
+	caddy_http_request_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="65536"} 1
+	caddy_http_request_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="262144"} 1
+	caddy_http_request_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="1.048576e+06"} 1
+	caddy_http_request_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="4.194304e+06"} 1
+	caddy_http_request_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="+Inf"} 1
+	caddy_http_request_size_bytes_sum{code="429",handler="foo",method="GET",server="UNKNOWN"} 23
+	caddy_http_request_size_bytes_count{code="429",handler="foo",method="GET",server="UNKNOWN"} 1
+	# HELP caddy_http_response_size_bytes Size of the returned response.
+	# TYPE caddy_http_response_size_bytes histogram
+	caddy_http_response_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="256"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="1024"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="4096"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="16384"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="65536"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="262144"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="1.048576e+06"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="4.194304e+06"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="bar",method="GET",server="UNKNOWN",le="+Inf"} 1
+	caddy_http_response_size_bytes_sum{code="200",handler="bar",method="GET",server="UNKNOWN"} 12
+	caddy_http_response_size_bytes_count{code="200",handler="bar",method="GET",server="UNKNOWN"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="256"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="1024"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="4096"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="16384"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="65536"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="262144"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="1.048576e+06"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="4.194304e+06"} 1
+	caddy_http_response_size_bytes_bucket{code="200",handler="empty",method="GET",server="UNKNOWN",le="+Inf"} 1
+	caddy_http_response_size_bytes_sum{code="200",handler="empty",method="GET",server="UNKNOWN"} 0
+	caddy_http_response_size_bytes_count{code="200",handler="empty",method="GET",server="UNKNOWN"} 1
+	caddy_http_response_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="256"} 1
+	caddy_http_response_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="1024"} 1
+	caddy_http_response_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="4096"} 1
+	caddy_http_response_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="16384"} 1
+	caddy_http_response_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="65536"} 1
+	caddy_http_response_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="262144"} 1
+	caddy_http_response_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="1.048576e+06"} 1
+	caddy_http_response_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="4.194304e+06"} 1
+	caddy_http_response_size_bytes_bucket{code="429",handler="foo",method="GET",server="UNKNOWN",le="+Inf"} 1
+	caddy_http_response_size_bytes_sum{code="429",handler="foo",method="GET",server="UNKNOWN"} 0
+	caddy_http_response_size_bytes_count{code="429",handler="foo",method="GET",server="UNKNOWN"} 1
+	# HELP caddy_http_request_errors_total Number of requests resulting in middleware errors.
+	# TYPE caddy_http_request_errors_total counter
+	caddy_http_request_errors_total{handler="bar",server="UNKNOWN"} 1
+	caddy_http_request_errors_total{handler="foo",server="UNKNOWN"} 1
+	`
+	if err := testutil.GatherAndCompare(prometheus.DefaultGatherer, strings.NewReader(expected),
+		"caddy_http_request_size_bytes",
+		"caddy_http_response_size_bytes",
+		// caddy_http_request_duration_seconds_sum will vary based on how long the test took to run,
+		// so we check just the _bucket and _count metrics
+		"caddy_http_request_duration_seconds_bucket",
+		"caddy_http_request_duration_seconds_count",
+		"caddy_http_request_errors_total",
+	); err != nil {
+		t.Errorf("received unexpected error: %s", err)
+	}
 }
 
 type middlewareHandlerFunc func(http.ResponseWriter, *http.Request, Handler) error