diff --git a/bitswap/network/httpnet/httpnet.go b/bitswap/network/httpnet/httpnet.go
index 939e4e4a5..cc7a53607 100644
--- a/bitswap/network/httpnet/httpnet.go
+++ b/bitswap/network/httpnet/httpnet.go
@@ -26,12 +26,13 @@ import (
 	"github.com/libp2p/go-libp2p/core/peerstore"
 	"github.com/libp2p/go-libp2p/p2p/protocol/ping"
 	"github.com/multiformats/go-multiaddr"
+	"go.uber.org/multierr"
 )
 
 var log = logging.Logger("httpnet")
 
 var ErrNoHTTPAddresses = errors.New("AddrInfo does not contain any valid HTTP addresses")
-var ErrNoSuccess = errors.New("none of the peer HTTP endpoints responded successfully to request")
+var ErrNoSuccess = errors.New("connection failed to all HTTP endpoints")
 var ErrNotConnected = errors.New("no HTTP connection has been setup to this peer")
 
 var _ network.BitSwapNetwork = (*Network)(nil)
@@ -411,6 +412,8 @@ func (ht *Network) Connect(ctx context.Context, pi peer.AddrInfo) error {
 
 	urls := network.ExtractURLsFromPeer(pi)
 
+	errs := []error{ErrNoSuccess}
+
 	// Filter addresses based on allow and denylists
 	var filteredURLs []network.ParsedURL
 	for _, u := range urls {
@@ -426,11 +429,13 @@ func (ht *Network) Connect(ctx context.Context, pi peer.AddrInfo) error {
 		_, denied := ht.denylist[host]
 		if allowed && !denied {
 			filteredURLs = append(filteredURLs, u)
+		} else {
+			errs = append(errs, fmt.Errorf("%s: address not allowed per allow/denylist", u.Multiaddress.String()))
 		}
 	}
 	urls = filteredURLs
 	if len(urls) == 0 {
-		return ErrNoHTTPAddresses
+		return multierr.Combine(errs...)
 	}
 	if len(urls) > ht.maxHTTPAddressesPerPeer {
 		urls = urls[0:ht.maxHTTPAddressesPerPeer]
@@ -446,9 +451,10 @@ func (ht *Network) Connect(ctx context.Context, pi peer.AddrInfo) error {
 		// If head works we assume GET works too.
 		err := ht.connectToURL(ctx, pi.ID, u, "HEAD")
 		if err != nil {
+			errs = append(errs, fmt.Errorf("%s: %s", u.Multiaddress.String(), err))
 			// abort if context cancelled
 			if ctxErr := ctx.Err(); ctxErr != nil {
-				return ctxErr
+				return multierr.Combine(errs...)
 			}
 		} else {
 			workingAddrs = append(workingAddrs, u.Multiaddress)
@@ -460,9 +466,9 @@ func (ht *Network) Connect(ctx context.Context, pi peer.AddrInfo) error {
 
 		err = ht.connectToURL(ctx, pi.ID, u, "GET")
 		if err != nil {
-			// abort if context cancelled
+			errs = append(errs, fmt.Errorf("%s: %s", u.Multiaddress.String(), err))
 			if errors.Is(err, context.Canceled) || errors.Is(err, context.DeadlineExceeded) {
-				return err
+				return multierr.Combine(errs...)
 			}
 			continue
 		}
@@ -471,7 +477,7 @@ func (ht *Network) Connect(ctx context.Context, pi peer.AddrInfo) error {
 
 	// Bail out if no working urls found.
 	if len(workingAddrs) == 0 {
-		return fmt.Errorf("connect failure to %s: %w", p, ErrNoSuccess)
+		return multierr.Combine(errs...)
 	}
 
 	// We have some working urls!
diff --git a/bitswap/network/httpnet/httpnet_test.go b/bitswap/network/httpnet/httpnet_test.go
index 8ed067814..e0a524e35 100644
--- a/bitswap/network/httpnet/httpnet_test.go
+++ b/bitswap/network/httpnet/httpnet_test.go
@@ -131,7 +131,9 @@ func mockNetwork(t *testing.T, recv network.Receiver, opts ...Option) (*Network,
 	if err != nil {
 		t.Fatal(err)
 	}
-	opts = append(opts, WithInsecureSkipVerify(true))
+
+	// allow ovewrite of default options by prepending them
+	opts = append([]Option{WithInsecureSkipVerify(true)}, opts...)
 	htnet := New(h, opts...)
 	htnet.Start(recv)
 	return htnet.(*Network), mn
@@ -282,20 +284,25 @@ func srvMultiaddr(t *testing.T, srv *httptest.Server) multiaddr.Multiaddr {
 	return maddr.Encapsulate(httpma)
 }
 
-func connectToPeer(t *testing.T, ctx context.Context, htnet *Network, remote host.Host, srvs ...*httptest.Server) {
+func connectToPeer(t *testing.T, ctx context.Context, htnet *Network, remote host.Host, srvs ...*httptest.Server) error {
 	var addrs []multiaddr.Multiaddr
 	for _, srv := range srvs {
 		addrs = append(addrs, srvMultiaddr(t, srv))
 	}
 
-	err := htnet.Connect(
+	return htnet.Connect(
 		ctx,
 		peer.AddrInfo{
 			ID:    remote.ID(),
 			Addrs: addrs,
 		},
 	)
-	if err != nil {
+}
+
+func mustConnectToPeer(t *testing.T, ctx context.Context, htnet *Network, remote host.Host, srvs ...*httptest.Server) {
+	t.Helper()
+
+	if err := connectToPeer(t, ctx, htnet, remote, srvs...); err != nil {
 		t.Fatal(err)
 	}
 }
@@ -308,7 +315,7 @@ func TestBestURL(t *testing.T) {
 		t.Fatal(err)
 	}
 	msrv := makeServer(t, 0, 0)
-	connectToPeer(t, ctx, htnet, peer, msrv)
+	mustConnectToPeer(t, ctx, htnet, peer, msrv)
 
 	nms, err := htnet.NewMessageSender(
 		ctx,
@@ -393,6 +400,48 @@ func TestBestURL(t *testing.T) {
 
 }
 
+func TestConnectErrors(t *testing.T) {
+	ctx := context.Background()
+	recv := mockReceiver(t)
+	msrv := makeServer(t, 0, 0)
+
+	htnet, mn := mockNetwork(t, recv,
+		WithInsecureSkipVerify(false),
+	)
+	peer, err := mn.GenPeer()
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	err = connectToPeer(t, ctx, htnet, peer, msrv)
+	if err == nil {
+		t.Fatal("expected error")
+	}
+	t.Log(err)
+	if !strings.Contains(err.Error(), "failed to verify") {
+		t.Error("wrong error")
+	}
+
+	htnet2, mn2 := mockNetwork(t, recv,
+		WithDenylist([]string{"127.0.0.1"}),
+	)
+
+	peer2, err := mn2.GenPeer()
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	err = connectToPeer(t, ctx, htnet2, peer2, msrv)
+	if err == nil {
+		t.Fatal("expected error")
+	}
+	t.Log(err)
+	if !strings.Contains(err.Error(), "denylist") {
+		t.Error("wrong error")
+	}
+
+}
+
 func TestSendMessage(t *testing.T) {
 	ctx := context.Background()
 	recv := mockReceiver(t)
@@ -402,7 +451,7 @@ func TestSendMessage(t *testing.T) {
 		t.Fatal(err)
 	}
 	msrv := makeServer(t, 0, 10)
-	connectToPeer(t, ctx, htnet, peer, msrv)
+	mustConnectToPeer(t, ctx, htnet, peer, msrv)
 
 	wl := makeCids(t, 0, 10)
 	msg := makeWantsMessage(wl)
@@ -431,7 +480,7 @@ func TestSendMessageWithFailingServer(t *testing.T) {
 	}
 	msrv := makeServer(t, 0, 0)
 	msrv2 := makeServer(t, 0, 10)
-	connectToPeer(t, ctx, htnet, peer, msrv, msrv2)
+	mustConnectToPeer(t, ctx, htnet, peer, msrv, msrv2)
 
 	wl := makeCids(t, 0, 10)
 	msg := makeWantsMessage(wl)
@@ -462,7 +511,7 @@ func TestSendMessageWithPartialResponse(t *testing.T) {
 		t.Fatal(err)
 	}
 	msrv := makeServer(t, 5, 10)
-	connectToPeer(t, ctx, htnet, peer, msrv)
+	mustConnectToPeer(t, ctx, htnet, peer, msrv)
 
 	wl := makeCids(t, 0, 10)
 	msg := makeWantsMessage(wl)
@@ -497,7 +546,7 @@ func TestSendMessageSendHavesAndDontHaves(t *testing.T) {
 		t.Fatal(err)
 	}
 	msrv := makeServer(t, 0, 5)
-	connectToPeer(t, ctx, htnet, peer, msrv)
+	mustConnectToPeer(t, ctx, htnet, peer, msrv)
 
 	wl := makeCids(t, 0, 10)
 	msg := makeHavesMessage(wl)
@@ -545,8 +594,8 @@ func TestBackOff(t *testing.T) {
 	}
 
 	msrv := makeServer(t, 0, 1)
-	connectToPeer(t, ctx, htnet, peer, msrv)
-	connectToPeer(t, ctx, htnet, peer2, msrv)
+	mustConnectToPeer(t, ctx, htnet, peer, msrv)
+	mustConnectToPeer(t, ctx, htnet, peer2, msrv)
 
 	nms, err := htnet.NewMessageSender(ctx, peer.ID(), nil)
 	if err != nil {
@@ -598,7 +647,7 @@ func TestErrorTracking(t *testing.T) {
 	}
 
 	msrv := makeServer(t, 0, 0)
-	connectToPeer(t, ctx, htnet, peer, msrv)
+	mustConnectToPeer(t, ctx, htnet, peer, msrv)
 
 	err = recv.waitConnected(1)
 	if err != nil {