diff --git a/packages/transport/stream/src/__tests__/stream.test.ts b/packages/transport/stream/src/__tests__/stream.test.ts
index 844405988..cabf3aefb 100644
--- a/packages/transport/stream/src/__tests__/stream.test.ts
+++ b/packages/transport/stream/src/__tests__/stream.test.ts
@@ -814,6 +814,73 @@ describe("streams", function () {
 			});
 
 			it("through relay if fails", async () => {
+				const dialFn =
+					streams[0].stream.components.connectionManager.openConnection.bind(
+						streams[0].stream.components.connectionManager
+					);
+
+				let directlyDialded = false;
+				const filteredDial = (address: PeerId | Multiaddr | Multiaddr[]) => {
+					if (
+						isPeerId(address) &&
+						address.toString() === streams[3].stream.peerIdStr
+					) {
+						throw new Error("Mock fail"); // don't allow connect directly
+					}
+
+					let addresses: Multiaddr[] = Array.isArray(address)
+						? address
+						: [address as Multiaddr];
+					for (const a of addresses) {
+						if (
+							!a.protoNames().includes("p2p-circuit") &&
+							a.toString().includes(streams[3].stream.peerIdStr)
+						) {
+							throw new Error("Mock fail"); // don't allow connect directly
+						}
+					}
+					addresses = addresses.map((x) =>
+						x.protoNames().includes("p2p-circuit")
+							? multiaddr(x.toString().replace("/webrtc/", "/"))
+							: x
+					); // TODO use webrtc in node
+
+					directlyDialded = true;
+					return dialFn(addresses);
+				};
+
+				streams[0].stream.components.connectionManager.openConnection =
+					filteredDial;
+				expect(streams[0].stream.peers.size).toEqual(1);
+				await streams[0].stream.publish(data, {
+					to: [streams[3].stream.components.peerId]
+				});
+				await waitFor(() => streams[3].received.length === 1);
+				await waitForResolved(() => expect(directlyDialded).toBeTrue());
+			});
+
+			it("tries multiple relays", async () => {
+				await session.connect([[session.peers[1], session.peers[3]]]);
+				await waitForPeerStreams(streams[1].stream, streams[3].stream);
+
+				/* 
+				┌───┐ 
+				│ 0 │ 
+				└┬─┬┘ 
+				 │┌▽┐ 
+				 ││1│ 
+				 │└┬┘ 
+				┌▽┐│  
+				│2││  
+				└┬┘│  
+				┌▽─▽─┐
+				│ 3  │
+				└────┘ 
+				
+				*/
+
+				const dialedCircuitRelayAddresses: Set<string> = new Set();
+
 				const dialFn =
 					streams[0].stream.components.connectionManager.openConnection.bind(
 						streams[0].stream.components.connectionManager
@@ -837,22 +904,32 @@ describe("streams", function () {
 							throw new Error("Mock fail"); // don't allow connect directly
 						}
 					}
-					const q = 123;
+					addresses
+						.filter((x) => x.protoNames().includes("p2p-circuit"))
+						.forEach((x) => {
+							dialedCircuitRelayAddresses.add(x.toString());
+						});
 					addresses = addresses.map((x) =>
-						x.protoCodes().includes(281)
+						x.protoNames().includes("p2p-circuit")
 							? multiaddr(x.toString().replace("/webrtc/", "/"))
 							: x
 					); // TODO use webrtc in node
+
+					if (dialedCircuitRelayAddresses.size === 1) {
+						throw new Error("Mock fail"); // only succeed with the dial once we have tried two unique addresses (both neighbors)
+					}
 					return dialFn(addresses);
 				};
 
 				streams[0].stream.components.connectionManager.openConnection =
 					filteredDial;
+
 				expect(streams[0].stream.peers.size).toEqual(1);
 				await streams[0].stream.publish(data, {
 					to: [streams[3].stream.components.peerId]
 				});
 				await waitFor(() => streams[3].received.length === 1);
+				expect(dialedCircuitRelayAddresses.size).toEqual(2);
 			});
 		});
 
diff --git a/packages/transport/stream/src/index.ts b/packages/transport/stream/src/index.ts
index 9ea7bedb0..1c66889a7 100644
--- a/packages/transport/stream/src/index.ts
+++ b/packages/transport/stream/src/index.ts
@@ -1412,7 +1412,7 @@ export abstract class DirectStream<
 								) {
 									// Dont await this even if it is async since this method can fail
 									// and might take some time to run
-									this.maybeConnectDirectly(path).catch((e) => {
+									this.maybeConnectDirectly(to).catch((e) => {
 										logger.error(
 											"Failed to request direct connection: " + e.message
 										);
@@ -1499,13 +1499,7 @@ export abstract class DirectStream<
 		}
 	}
 
-	async maybeConnectDirectly(path: string[]) {
-		if (path.length < 3) {
-			return;
-		}
-
-		const toHash = path[path.length - 1];
-
+	async maybeConnectDirectly(toHash: string) {
 		if (this.peers.has(toHash)) {
 			return; // TODO, is this expected, or are we to dial more addresses?
 		}
@@ -1527,49 +1521,51 @@ export abstract class DirectStream<
 		}
 
 		// Connect through a closer relay that maybe does holepunch for us
-		const nextToHash = path[path.length - 2];
-		const routeKey = nextToHash + toHash;
-		if (!this.recentDials.has(routeKey)) {
-			this.recentDials.add(routeKey);
-			const to = this.peerKeyHashToPublicKey.get(toHash)! as Ed25519PublicKey;
-			const toPeerId = await to.toPeerId();
-			const addrs = this.multiaddrsMap.get(path[path.length - 2]);
-			if (addrs && addrs.length > 0) {
-				const addressesToDial = addrs.sort((a, b) => {
-					if (a.includes("/wss/")) {
-						if (b.includes("/wss/")) {
-							return 0;
-						}
-						return -1;
-					}
-					if (a.includes("/ws/")) {
-						if (b.includes("/ws/")) {
-							return 0;
+		const neighbours = this.routes.graph.neighbors(toHash);
+		outer: for (const neighbour of neighbours) {
+			const routeKey = neighbour + toHash;
+			if (!this.recentDials.has(routeKey)) {
+				this.recentDials.add(routeKey);
+				const to = this.peerKeyHashToPublicKey.get(toHash)! as Ed25519PublicKey;
+				const toPeerId = await to.toPeerId();
+				const addrs = this.multiaddrsMap.get(neighbour);
+				if (addrs && addrs.length > 0) {
+					const addressesToDial = addrs.sort((a, b) => {
+						if (a.includes("/wss/")) {
+							if (b.includes("/wss/")) {
+								return 0;
+							}
+							return -1;
 						}
-						if (b.includes("/wss/")) {
-							return 1;
+						if (a.includes("/ws/")) {
+							if (b.includes("/ws/")) {
+								return 0;
+							}
+							if (b.includes("/wss/")) {
+								return 1;
+							}
+							return -1;
 						}
-						return -1;
-					}
-					return 0;
-				});
+						return 0;
+					});
 
-				for (const addr of addressesToDial) {
-					const circuitAddress = multiaddr(
-						addr + "/p2p-circuit/webrtc/p2p/" + toPeerId.toString()
-					);
-					try {
-						await this.components.connectionManager.openConnection(
-							circuitAddress
-						);
-						return;
-					} catch (error: any) {
-						logger.error(
-							"Failed to connect directly to: " +
-								circuitAddress.toString() +
-								". " +
-								error?.message
+					for (const addr of addressesToDial) {
+						const circuitAddress = multiaddr(
+							addr + "/p2p-circuit/webrtc/p2p/" + toPeerId.toString()
 						);
+						try {
+							await this.components.connectionManager.openConnection(
+								circuitAddress
+							);
+							break outer; // We succeeded! that means we dont have to try anymore
+						} catch (error: any) {
+							logger.warn(
+								"Failed to connect directly to: " +
+									circuitAddress.toString() +
+									". " +
+									error?.message
+							);
+						}
 					}
 				}
 			}