diff --git a/peer/brontide.go b/peer/brontide.go
index 578d7133..c0669cdf 100644
--- a/peer/brontide.go
+++ b/peer/brontide.go
@@ -446,9 +446,36 @@ func (p *Brontide) Start() error {
 
 	peerLog.Tracef("Peer %v starting", p)
 
+	// Fetch and then load all the active channels we have with this remote
+	// peer from the database.
+	activeChans, err := p.cfg.ChannelDB.FetchOpenChannels(
+		p.cfg.Addr.IdentityKey,
+	)
+	if err != nil {
+		peerLog.Errorf("Unable to fetch active chans "+
+			"for peer %v: %v", p, err)
+		return err
+	}
+
+	if len(activeChans) == 0 {
+		p.cfg.PrunePersistentPeerConnection(p.cfg.PubKeyBytes)
+	}
+
+	// Quickly check if we have any existing legacy channels with this
+	// peer.
+	haveLegacyChan := false
+	for _, c := range activeChans {
+		if c.ChanType.IsTweakless() {
+			continue
+		}
+
+		haveLegacyChan = true
+		break
+	}
+
 	// Exchange local and global features, the init message should be very
 	// first between two nodes.
-	if err := p.sendInitMsg(); err != nil {
+	if err := p.sendInitMsg(haveLegacyChan); err != nil {
 		return fmt.Errorf("unable to send init msg: %v", err)
 	}
 
@@ -496,19 +523,6 @@ func (p *Brontide) Start() error {
 			"must be init message")
 	}
 
-	// Fetch and then load all the active channels we have with this remote
-	// peer from the database.
-	activeChans, err := p.cfg.ChannelDB.FetchOpenChannels(p.cfg.Addr.IdentityKey)
-	if err != nil {
-		peerLog.Errorf("unable to fetch active chans "+
-			"for peer %v: %v", p, err)
-		return err
-	}
-
-	if len(activeChans) == 0 {
-		p.cfg.PrunePersistentPeerConnection(p.cfg.PubKeyBytes)
-	}
-
 	// Next, load all the active channels we have with this peer,
 	// registering them with the switch and launching the necessary
 	// goroutines required to operate them.
@@ -2752,12 +2766,28 @@ func (p *Brontide) RemoteFeatures() *lnwire.FeatureVector {
 	return p.remoteFeatures
 }
 
-// sendInitMsg sends the Init message to the remote peer. This message contains our
-// currently supported local and global features.
-func (p *Brontide) sendInitMsg() error {
+// sendInitMsg sends the Init message to the remote peer. This message contains
+// our currently supported local and global features.
+func (p *Brontide) sendInitMsg(legacyChan bool) error {
+	features := p.cfg.Features.Clone()
+
+	// If we have a legacy channel open with a peer, we downgrade static
+	// remote required to optional in case the peer does not understand the
+	// required feature bit. If we do not do this, the peer will reject our
+	// connection because it does not understand a required feature bit, and
+	// our channel will be unusable.
+	if legacyChan && features.RequiresFeature(lnwire.StaticRemoteKeyRequired) {
+		peerLog.Infof("Legacy channel open with peer: %x, "+
+			"downgrading static remote required feature bit to "+
+			"optional", p.PubKey())
+
+		features.Unset(lnwire.StaticRemoteKeyRequired)
+		features.Set(lnwire.StaticRemoteKeyOptional)
+	}
+
 	msg := lnwire.NewInitMessage(
 		p.cfg.LegacyFeatures.RawFeatureVector,
-		p.cfg.Features.RawFeatureVector,
+		features.RawFeatureVector,
 	)
 
 	return p.writeMessage(msg)