diff --git a/CHANGELOG.md b/CHANGELOG.md
index 98fd3df7d254..7b8d1061af73 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -106,6 +106,7 @@ Ref: https://keepachangelog.com/en/1.0.0/
 `cosmossdk.io/core/appmodule.AppModule` API via the new `NewManagerFromMap` constructor.
 * [#14019](https://github.com/cosmos/cosmos-sdk/issues/14019) Remove the interface casting to allow other implementations of a `CommitMultiStore`.
 * [#13881](https://github.com/cosmos/cosmos-sdk/pull/13881) Optimize iteration on nested cached KV stores and other operations in general.
+* (x/gov) [#14347](https://github.com/cosmos/cosmos-sdk/pull/14347) Support `v1.Proposal` message in `v1beta1.Proposal.Content`.
 
 ### State Machine Breaking
 
diff --git a/x/gov/migrations/v3/convert.go b/x/gov/migrations/v3/convert.go
index 0e7ae37359d4..7c9c111eb31a 100644
--- a/x/gov/migrations/v3/convert.go
+++ b/x/gov/migrations/v3/convert.go
@@ -5,6 +5,7 @@ import (
 
 	codectypes "github.com/cosmos/cosmos-sdk/codec/types"
 	"github.com/cosmos/cosmos-sdk/types"
+	sdkerrors "github.com/cosmos/cosmos-sdk/types/errors"
 	authtypes "github.com/cosmos/cosmos-sdk/x/auth/types"
 	v1 "github.com/cosmos/cosmos-sdk/x/gov/types/v1"
 	"github.com/cosmos/cosmos-sdk/x/gov/types/v1beta1"
@@ -13,6 +14,7 @@ import (
 // ConvertToLegacyProposal takes a new proposal and attempts to convert it to the
 // legacy proposal format. This conversion is best effort. New proposal types that
 // don't have a legacy message will return a "nil" content.
+// Returns error when the amount of messages in `proposal` is different than one.
 func ConvertToLegacyProposal(proposal v1.Proposal) (v1beta1.Proposal, error) {
 	var err error
 	legacyProposal := v1beta1.Proposal{
@@ -46,6 +48,9 @@ func ConvertToLegacyProposal(proposal v1.Proposal) (v1beta1.Proposal, error) {
 	if err != nil {
 		return v1beta1.Proposal{}, err
 	}
+	if len(msgs) != 1 {
+		return v1beta1.Proposal{}, sdkerrors.ErrInvalidType.Wrap("can't convert a gov/v1 Proposal to gov/v1beta1 Proposal when amount of proposal messages is more than one")
+	}
 	for _, msg := range msgs {
 		if legacyMsg, ok := msg.(*v1.MsgExecLegacyContent); ok {
 			// check that the content struct can be unmarshalled
@@ -54,9 +59,16 @@ func ConvertToLegacyProposal(proposal v1.Proposal) (v1beta1.Proposal, error) {
 				return v1beta1.Proposal{}, err
 			}
 			legacyProposal.Content = legacyMsg.Content
+			return legacyProposal, nil
 		}
 	}
-	return legacyProposal, nil
+	// hack to fill up the content with the first message
+	// this is to support clients that have not yet (properly) use gov/v1 endpoints
+	// https://github.com/cosmos/cosmos-sdk/issues/14334
+	// VerifyBasic assures that we have at least one message.
+	legacyProposal.Content, err = codectypes.NewAnyWithValue(msgs[0])
+
+	return legacyProposal, err
 }
 
 func ConvertToLegacyTallyResult(tally *v1.TallyResult) (v1beta1.TallyResult, error) {
diff --git a/x/gov/migrations/v3/convert_test.go b/x/gov/migrations/v3/convert_test.go
index 5196a8f33bdd..a54bbdc02068 100644
--- a/x/gov/migrations/v3/convert_test.go
+++ b/x/gov/migrations/v3/convert_test.go
@@ -6,10 +6,12 @@ import (
 
 	"cosmossdk.io/math"
 	sdk "github.com/cosmos/cosmos-sdk/types"
+	sdkerrors "github.com/cosmos/cosmos-sdk/types/errors"
 	"github.com/cosmos/cosmos-sdk/types/tx"
 	v3 "github.com/cosmos/cosmos-sdk/x/gov/migrations/v3"
 	v1 "github.com/cosmos/cosmos-sdk/x/gov/types/v1"
 	"github.com/cosmos/cosmos-sdk/x/gov/types/v1beta1"
+	upgradetypes "github.com/cosmos/cosmos-sdk/x/upgrade/types"
 	"github.com/stretchr/testify/require"
 )
 
@@ -62,11 +64,46 @@ func TestConvertToLegacyProposal(t *testing.T) {
 				require.Equal(t, v1beta1Proposal.FinalTallyResult.No, sdk.NewInt(0))
 				require.Equal(t, v1beta1Proposal.FinalTallyResult.NoWithVeto, sdk.NewInt(0))
 				require.Equal(t, v1beta1Proposal.FinalTallyResult.Abstain, sdk.NewInt(0))
+				tp, ok := v1beta1Proposal.Content.GetCachedValue().(*v1beta1.TextProposal)
+				require.Truef(t, ok, "expected *TextProposal, got %T", v1beta1Proposal.Content.GetCachedValue())
+				require.Equal(t, tp.Title, "title")
+				require.Equal(t, tp.Description, "description")
 			}
 		})
 	}
 }
 
+func TestConvertToLegacyProposalContent(t *testing.T) {
+	msg := upgradetypes.MsgSoftwareUpgrade{Authority: "gov module", Plan: upgradetypes.Plan{Name: "test upgrade"}}
+	msgsAny, err := tx.SetMsgs([]sdk.Msg{&msg})
+	require.NoError(t, err)
+	tallyResult := v1.EmptyTallyResult()
+	proposal := v1.Proposal{
+		Id:               1,
+		Status:           v1.StatusDepositPeriod,
+		Messages:         msgsAny,
+		Metadata:         "proposal metadata",
+		FinalTallyResult: &tallyResult,
+	}
+
+	legacyP, err := v3.ConvertToLegacyProposal(proposal)
+	require.NoError(t, err)
+	tp, ok := legacyP.Content.GetCachedValue().(*upgradetypes.MsgSoftwareUpgrade)
+	require.Truef(t, ok, "expected *MsgSoftwareUpgrade, got %T", legacyP.Content.GetCachedValue())
+	require.Equal(t, &msg, tp)
+
+	// more than one message is not supported
+	proposal.Messages, err = tx.SetMsgs([]sdk.Msg{&msg, &msg})
+	require.NoError(t, err)
+	_, err = v3.ConvertToLegacyProposal(proposal)
+	require.ErrorIs(t, sdkerrors.ErrInvalidType, err)
+
+	// zero messages is not supported
+	proposal.Messages = nil
+	_, err = v3.ConvertToLegacyProposal(proposal)
+	require.ErrorIs(t, sdkerrors.ErrInvalidType, err)
+}
+
 func TestConvertToLegacyTallyResult(t *testing.T) {
 	tallyResult := v1.EmptyTallyResult()
 	testCases := map[string]struct {