diff --git a/libp2p/exceptions.py b/libp2p/exceptions.py
index bdecfad..5b78114 100644
--- a/libp2p/exceptions.py
+++ b/libp2p/exceptions.py
@@ -8,3 +8,9 @@ class ValidationError(BaseLibp2pError):
 
 class ParseError(BaseLibp2pError):
     pass
+
+
+class MultiError(BaseLibp2pError):
+    """Raised with multiple exceptions."""
+
+    # todo: find some way for this to fancy-print all encapsulated errors
diff --git a/libp2p/network/swarm.py b/libp2p/network/swarm.py
index 0c40510..c861877 100644
--- a/libp2p/network/swarm.py
+++ b/libp2p/network/swarm.py
@@ -19,6 +19,7 @@ from libp2p.transport.transport_interface import ITransport
 from libp2p.transport.upgrader import TransportUpgrader
 from libp2p.typing import StreamHandlerFn
 
+from ..exceptions import MultiError
 from .connection.raw_connection import RawConnection
 from .connection.swarm_connection import SwarmConn
 from .exceptions import SwarmException
@@ -87,21 +88,51 @@ class Swarm(INetwork):
         try:
             # Get peer info from peer store
             addrs = self.peerstore.addrs(peer_id)
-        except PeerStoreError:
-            raise SwarmException(f"No known addresses to peer {peer_id}")
+        except PeerStoreError as error:
+            raise SwarmException(f"No known addresses to peer {peer_id}") from error
 
         if not addrs:
             raise SwarmException(f"No known addresses to peer {peer_id}")
 
-        multiaddr = addrs[0]
+        exceptions: List[SwarmException] = []
+
+        # Try all known addresses
+        for multiaddr in addrs:
+            try:
+                return await self.dial_addr(multiaddr, peer_id)
+            except SwarmException as e:
+                exceptions.append(e)
+                logger.debug(
+                    "encountered swarm exception when trying to connect to %s, "
+                    "trying next address...",
+                    multiaddr,
+                    exc_info=e,
+                )
+
+        # Tried all addresses, raising exception.
+        raise SwarmException(
+            f"unable to connect to {peer_id}, no addresses established a successful connection "
+            "(with exceptions)"
+        ) from MultiError(exceptions)
+
+    async def dial_addr(self, addr: Multiaddr, peer_id: ID) -> INetConn:
+        """
+        dial_addr try to create a connection to peer_id with addr.
+
+        :param addr: the address we want to connect with
+        :param peer_id: the peer we want to connect to
+        :raises SwarmException: raised when an error occurs
+        :return: network connection
+        """
+
         # Dial peer (connection to peer does not yet exist)
         # Transport dials peer (gets back a raw conn)
         try:
-            raw_conn = await self.transport.dial(multiaddr)
+            raw_conn = await self.transport.dial(addr)
         except OpenConnectionError as error:
             logger.debug("fail to dial peer %s over base transport", peer_id)
             raise SwarmException(
-                "fail to open connection to peer %s", peer_id
+                f"fail to open connection to peer {peer_id}"
             ) from error
 
         logger.debug("dialed peer %s over base transport", peer_id)
@@ -137,7 +168,6 @@ class Swarm(INetwork):
     async def new_stream(self, peer_id: ID) -> INetStream:
         """
         :param peer_id: peer_id of destination
-        :param protocol_id: protocol id
         :raises SwarmException: raised when an error occurs
         :return: net stream instance
         """
diff --git a/tests/network/test_swarm.py b/tests/network/test_swarm.py
index 6fe2543..3cc9375 100644
--- a/tests/network/test_swarm.py
+++ b/tests/network/test_swarm.py
@@ -1,5 +1,6 @@
 import asyncio
 
+from multiaddr import Multiaddr
 import pytest
 
 from libp2p.network.exceptions import SwarmException
@@ -91,3 +92,59 @@ async def test_swarm_remove_conn(swarm_pair):
     # Test: Remove twice. There should not be errors.
     swarm_0.remove_conn(conn_0)
     assert swarm_1.get_peer_id() not in swarm_0.connections
+
+
+@pytest.mark.asyncio
+async def test_swarm_multiaddr(is_host_secure):
+    swarms = await SwarmFactory.create_batch_and_listen(is_host_secure, 3)
+
+    def clear():
+        swarms[0].peerstore.clear_addrs(swarms[1].get_peer_id())
+
+    clear()
+    # No addresses
+    with pytest.raises(SwarmException):
+        await swarms[0].dial_peer(swarms[1].get_peer_id())
+
+    clear()
+    # Wrong addresses
+    swarms[0].peerstore.add_addrs(
+        swarms[1].get_peer_id(), [Multiaddr("/ip4/0.0.0.0/tcp/9999")], 10000
+    )
+
+    with pytest.raises(SwarmException):
+        await swarms[0].dial_peer(swarms[1].get_peer_id())
+
+    clear()
+    # Multiple wrong addresses
+    swarms[0].peerstore.add_addrs(
+        swarms[1].get_peer_id(),
+        [Multiaddr("/ip4/0.0.0.0/tcp/9999"), Multiaddr("/ip4/0.0.0.0/tcp/9998")],
+        10000,
+    )
+
+    with pytest.raises(SwarmException):
+        await swarms[0].dial_peer(swarms[1].get_peer_id())
+
+    # Test one address
+    addrs = tuple(
+        addr
+        for transport in swarms[1].listeners.values()
+        for addr in transport.get_addrs()
+    )
+
+    swarms[0].peerstore.add_addrs(swarms[1].get_peer_id(), addrs[:1], 10000)
+    await swarms[0].dial_peer(swarms[1].get_peer_id())
+
+    # Test multiple addresses
+    addrs = tuple(
+        addr
+        for transport in swarms[1].listeners.values()
+        for addr in transport.get_addrs()
+    )
+
+    swarms[0].peerstore.add_addrs(swarms[1].get_peer_id(), addrs + addrs, 10000)
+    await swarms[0].dial_peer(swarms[1].get_peer_id())
+
+    for swarm in swarms:
+        await swarm.close()