diff --git a/pkg/kncloudevents/message_sender.go b/pkg/kncloudevents/message_sender.go
index 5cbe26a985e..e3fe6ecec8b 100644
--- a/pkg/kncloudevents/message_sender.go
+++ b/pkg/kncloudevents/message_sender.go
@@ -189,6 +189,6 @@ func RetryConfigFromDeliverySpec(spec duckv1.DeliverySpec) (RetryConfig, error)
 	return retryConfig, nil
 }
 
-func checkRetry(_ context.Context, resp *nethttp.Response, _ error) (bool, error) {
-	return resp != nil && resp.StatusCode >= 300, nil
+func checkRetry(_ context.Context, resp *nethttp.Response, err error) (bool, error) {
+	return !(resp != nil && resp.StatusCode < 300), err
 }
diff --git a/pkg/kncloudevents/message_sender_test.go b/pkg/kncloudevents/message_sender_test.go
index 1cbffcc3d05..202bbde7764 100644
--- a/pkg/kncloudevents/message_sender_test.go
+++ b/pkg/kncloudevents/message_sender_test.go
@@ -18,6 +18,10 @@ package kncloudevents
 
 import (
 	"context"
+	"fmt"
+	"math"
+	"math/rand"
+	"net"
 	"net/http"
 	"net/http/httptest"
 	"sync/atomic"
@@ -180,6 +184,86 @@ func TestHTTPMessageSenderSendWithRetries(t *testing.T) {
 	}
 }
 
+func TestRetriesOnNetworkErrors(t *testing.T) {
+
+	port := rand.Int31n(math.MaxUint16-1024) + 1024
+	n := int32(10)
+	linear := duckv1.BackoffPolicyLinear
+	target := fmt.Sprintf("127.0.0.1:%d", port)
+
+	calls := make(chan struct{})
+	defer close(calls)
+
+	nCalls := int32(0)
+
+	cont := make(chan struct{})
+	defer close(cont)
+
+	go func() {
+		for range calls {
+
+			nCalls++
+
+			// Simulate that the target service is back up.
+			//
+			// First n/2-1 calls we get connection refused since there is no server running.
+			// Now we start a server that responds with a retryable error, so we expect that
+			// the client continues to retry for a different reason.
+			//
+			// The last time we return 200, so we don't expect a new retry.
+			if n/2 == nCalls {
+
+				l, err := net.Listen("tcp", target)
+				assert.Nil(t, err)
+
+				s := httptest.NewUnstartedServer(http.HandlerFunc(func(writer http.ResponseWriter, request *http.Request) {
+					if n-1 != nCalls {
+						writer.WriteHeader(http.StatusServiceUnavailable)
+						return
+					}
+				}))
+				defer s.Close()
+
+				assert.Nil(t, s.Listener.Close())
+
+				s.Listener = l
+
+				s.Start()
+			}
+			cont <- struct{}{}
+		}
+	}()
+
+	r, err := RetryConfigFromDeliverySpec(duckv1.DeliverySpec{
+		Retry:         pointer.Int32Ptr(n),
+		BackoffPolicy: &linear,
+		BackoffDelay:  pointer.StringPtr("PT0.1S"),
+	})
+	assert.Nil(t, err)
+
+	checkRetry := r.CheckRetry
+
+	r.CheckRetry = func(ctx context.Context, resp *http.Response, err error) (bool, error) {
+		calls <- struct{}{}
+		<-cont
+
+		return checkRetry(ctx, resp, err)
+	}
+
+	req, err := http.NewRequest("POST", "http://"+target, nil)
+	assert.Nil(t, err)
+
+	sender, err := NewHTTPMessageSender(nil, "")
+	assert.Nil(t, err)
+
+	_, err = sender.SendWithRetries(req, &r)
+	assert.Nil(t, err)
+
+	// nCalls keeps track of how many times a call to check retry occurs.
+	// Since the number of request are n + 1 and the last one is successful the expected number of calls are n.
+	assert.Equal(t, n, nCalls, "expected %d got %d", n, nCalls)
+}
+
 func TestHTTPMessageSenderSendWithRetriesWithBufferedMessage(t *testing.T) {
 	t.Parallel()