diff --git a/e2e/tests/core/04-channel/upgrades_test.go b/e2e/tests/core/04-channel/upgrades_test.go
index b3cd671911a..e837ec41e7f 100644
--- a/e2e/tests/core/04-channel/upgrades_test.go
+++ b/e2e/tests/core/04-channel/upgrades_test.go
@@ -4,6 +4,7 @@ package channel
 
 import (
 	"context"
+	"sync"
 	"testing"
 
 	"github.com/strangelove-ventures/interchaintest/v8/ibc"
@@ -235,6 +236,95 @@ func (s *ChannelTestSuite) TestChannelUpgrade_WithFeeMiddleware_Succeeds() {
 	})
 }
 
+// TestChannelUpgrade_WithFeeMiddleware_CrossingHello_Succeeds tests upgrading a transfer channel to wire up fee middleware under crossing hello
+func (s *ChannelTestSuite) TestChannelUpgrade_WithFeeMiddleware_CrossingHello_Succeeds() {
+	t := s.T()
+	ctx := context.TODO()
+
+	relayer, channelA := s.SetupChainsRelayerAndChannel(ctx, s.TransferChannelOptions())
+	channelB := channelA.Counterparty
+	chainA, chainB := s.GetChains()
+
+	chainADenom := chainA.Config().Denom
+
+	chainAWallet := s.CreateUserOnChainA(ctx, testvalues.StartingTokenAmount)
+	chainAAddress := chainAWallet.FormattedAddress()
+
+	chainBWallet := s.CreateUserOnChainB(ctx, testvalues.StartingTokenAmount)
+	chainBAddress := chainBWallet.FormattedAddress()
+
+	s.Require().NoError(test.WaitForBlocks(ctx, 1, chainA, chainB), "failed to wait for blocks")
+
+	// trying to create some inflight packets, although they might get relayed before the upgrade starts
+	t.Run("create inflight transfer packets between chain A and chain B", func(t *testing.T) {
+		transferTxResp := s.Transfer(ctx, chainA, chainAWallet, channelA.PortID, channelA.ChannelID, testvalues.DefaultTransferAmount(chainADenom), chainAAddress, chainBAddress, s.GetTimeoutHeight(ctx, chainB), 0, "")
+		s.AssertTxSuccess(transferTxResp)
+	})
+
+	t.Run("start relayer", func(t *testing.T) {
+		s.StartRelayer(relayer)
+	})
+
+	t.Run("execute gov proposals to initiate channel upgrade on chain A and chain B", func(t *testing.T) {
+		var wg sync.WaitGroup
+
+		wg.Add(1)
+		go func() {
+			defer wg.Done()
+			chA, err := s.QueryChannel(ctx, chainA, channelA.PortID, channelA.ChannelID)
+			s.Require().NoError(err)
+			s.initiateChannelUpgrade(ctx, chainA, chainAWallet, channelA.PortID, channelA.ChannelID, s.createUpgradeFields(chA))
+		}()
+
+		wg.Add(1)
+		go func() {
+			defer wg.Done()
+			chB, err := s.QueryChannel(ctx, chainB, channelB.PortID, channelB.ChannelID)
+			s.Require().NoError(err)
+			s.initiateChannelUpgrade(ctx, chainB, chainBWallet, channelB.PortID, channelB.ChannelID, s.createUpgradeFields(chB))
+		}()
+
+		wg.Wait()
+	})
+
+	s.Require().NoError(test.WaitForBlocks(ctx, 10, chainA, chainB), "failed to wait for blocks")
+
+	t.Run("packets are relayed between chain A and chain B", func(t *testing.T) {
+		// packet from chain A to chain B
+		s.AssertPacketRelayed(ctx, chainA, channelA.PortID, channelA.ChannelID, 1)
+	})
+
+	t.Run("verify channel A upgraded and is fee enabled", func(t *testing.T) {
+		channel, err := s.QueryChannel(ctx, chainA, channelA.PortID, channelA.ChannelID)
+		s.Require().NoError(err)
+
+		// check the channel version include the fee version
+		version, err := feetypes.MetadataFromVersion(channel.Version)
+		s.Require().NoError(err)
+		s.Require().Equal(feetypes.Version, version.FeeVersion, "the channel version did not include ics29")
+
+		// extra check
+		feeEnabled, err := s.QueryFeeEnabledChannel(ctx, chainA, channelA.PortID, channelA.ChannelID)
+		s.Require().NoError(err)
+		s.Require().Equal(true, feeEnabled)
+	})
+
+	t.Run("verify channel B upgraded and is fee enabled", func(t *testing.T) {
+		channel, err := s.QueryChannel(ctx, chainB, channelB.PortID, channelB.ChannelID)
+		s.Require().NoError(err)
+
+		// check the channel version include the fee version
+		version, err := feetypes.MetadataFromVersion(channel.Version)
+		s.Require().NoError(err)
+		s.Require().Equal(feetypes.Version, version.FeeVersion, "the channel version did not include ics29")
+
+		// extra check
+		feeEnabled, err := s.QueryFeeEnabledChannel(ctx, chainB, channelB.PortID, channelB.ChannelID)
+		s.Require().NoError(err)
+		s.Require().Equal(true, feeEnabled)
+	})
+}
+
 // TestChannelUpgrade_WithFeeMiddleware_FailsWithTimeoutOnAck tests upgrading a transfer channel to wire up fee middleware but fails on ACK because of timeout
 func (s *ChannelTestSuite) TestChannelUpgrade_WithFeeMiddleware_FailsWithTimeoutOnAck() {
 	t := s.T()