diff --git a/src/Simplex/Messaging/Agent/Client.hs b/src/Simplex/Messaging/Agent/Client.hs
index b8614c460..43b3b8064 100644
--- a/src/Simplex/Messaging/Agent/Client.hs
+++ b/src/Simplex/Messaging/Agent/Client.hs
@@ -597,10 +597,10 @@ getSMPServerClient c@AgentClient {active, smpClients, workerSeq} tSess = do
       prs <- atomically TM.empty
       smpConnectClient c tSess prs v
 
-getSMPProxyClient :: AgentClient -> SMPTransportSession -> AM (SMPConnectedClient, Either AgentErrorType ProxiedRelay)
-getSMPProxyClient c@AgentClient {active, smpClients, smpProxiedRelays, workerSeq} destSess@(userId, destSrv, qId) = do
+getSMPProxyClient :: AgentClient -> Maybe SMPServerWithAuth -> SMPTransportSession -> AM (SMPConnectedClient, Either AgentErrorType ProxiedRelay)
+getSMPProxyClient c@AgentClient {active, smpClients, smpProxiedRelays, workerSeq} proxySrv_ destSess@(userId, destSrv, qId) = do
   unlessM (readTVarIO active) $ throwE INACTIVE
-  proxySrv <- getNextServer c userId [destSrv]
+  proxySrv <- maybe (getNextServer c userId [destSrv]) pure proxySrv_
   ts <- liftIO getCurrentTime
   atomically (getClientVar proxySrv ts) >>= \(tSess, auth, v) ->
     either (newProxyClient tSess auth ts) (waitForProxyClient tSess auth) v
@@ -993,9 +993,9 @@ withClient_ c tSess@(_, srv, _) action = do
       logServer "<--" c srv "" $ bshow e
       throwE e
 
-withProxySession :: AgentClient -> SMPTransportSession -> SMP.SenderId -> ByteString -> ((SMPConnectedClient, ProxiedRelay) -> AM a) -> AM a
-withProxySession c destSess@(_, destSrv, _) entId cmdStr action = do
-  (cl, sess_) <- getSMPProxyClient c destSess
+withProxySession :: AgentClient -> Maybe SMPServerWithAuth -> SMPTransportSession -> SMP.SenderId -> ByteString -> ((SMPConnectedClient, ProxiedRelay) -> AM a) -> AM a
+withProxySession c proxySrv_ destSess@(_, destSrv, _) entId cmdStr action = do
+  (cl, sess_) <- getSMPProxyClient c proxySrv_ destSess
   logServer ("--> " <> proxySrv cl <> " >") c destSrv entId cmdStr
   case sess_ of
     Right sess -> do
@@ -1053,7 +1053,7 @@ sendOrProxySMPCommand ::
   AM (Maybe SMPServer)
 sendOrProxySMPCommand c userId destSrv cmdStr senderId sendCmdViaProxy sendCmdDirectly = do
   sess <- liftIO $ mkTransportSession c userId destSrv senderId
-  ifM (atomically shouldUseProxy) (sendViaProxy sess) (sendDirectly sess $> Nothing)
+  ifM (atomically shouldUseProxy) (sendViaProxy Nothing sess) (sendDirectly sess $> Nothing)
   where
     shouldUseProxy = do
       cfg <- getNetworkConfig c
@@ -1071,22 +1071,31 @@ sendOrProxySMPCommand c userId destSrv cmdStr senderId sendCmdViaProxy sendCmdDi
         SPFAllowProtected -> ipAddressProtected cfg destSrv
         SPFProhibit -> False
     unknownServer = maybe True (notElem destSrv . knownSrvs) <$> TM.lookup userId (smpServers c)
-    sendViaProxy destSess@(_, _, qId) = do
-      r <- tryAgentError . withProxySession c destSess senderId ("PFWD " <> cmdStr) $ \(SMPConnectedClient smp _, proxySess) -> do
+    sendViaProxy :: Maybe SMPServerWithAuth -> SMPTransportSession -> AM (Maybe SMPServer)
+    sendViaProxy proxySrv_ destSess@(_, _, qId) = do
+      r <- tryAgentError . withProxySession c proxySrv_ destSess senderId ("PFWD " <> cmdStr) $ \(SMPConnectedClient smp _, proxySess@ProxiedRelay {prBasicAuth}) -> do
         r' <- liftClient SMP (clientServer smp) $ sendCmdViaProxy smp proxySess
+        let proxySrv = protocolClientServer' smp
         case r' of
-          Right () -> pure . Just $ protocolClientServer' smp
+          Right () -> pure $ Just proxySrv
           Left proxyErr -> do
             case proxyErr of
-              (ProxyProtocolError (SMP.PROXY SMP.NO_SESSION)) -> atomically deleteRelaySession
-              _ -> pure ()
-            throwE
-              PROXY
-                { proxyServer = protocolClientServer smp,
-                  relayServer = B.unpack $ strEncode destSrv,
-                  proxyErr
-                }
+              ProxyProtocolError (SMP.PROXY SMP.NO_SESSION) -> do
+                atomically deleteRelaySession
+                case proxySrv_ of
+                  Just _ -> proxyError
+                  -- sendViaProxy is called recursively here to re-create the session via the same server
+                  -- to avoid failure in interactive calls that don't retry after the session disconnection.
+                  Nothing -> sendViaProxy (Just $ ProtoServerWithAuth proxySrv prBasicAuth) destSess
+              _ -> proxyError
             where
+              proxyError =
+                throwE
+                  PROXY
+                    { proxyServer = protocolClientServer smp,
+                      relayServer = B.unpack $ strEncode destSrv,
+                      proxyErr
+                    }
               -- checks that the current proxied relay session is the same one that was used to send the message and removes it
               deleteRelaySession =
                 ( TM.lookup destSess (smpProxiedRelays c)
diff --git a/src/Simplex/Messaging/Client.hs b/src/Simplex/Messaging/Client.hs
index 1837a256b..4b1e673b0 100644
--- a/src/Simplex/Messaging/Client.hs
+++ b/src/Simplex/Messaging/Client.hs
@@ -823,7 +823,7 @@ connectSMPProxiedRelay c@ProtocolClient {client_ = PClient {tcpConnectTimeout, t
         PKEY sId vr (chain, key) ->
           case supportedClientSMPRelayVRange `compatibleVersion` vr of
             Nothing -> throwE $ transportErr TEVersion
-            Just (Compatible v) -> liftEitherWith (const $ transportErr $ TEHandshake IDENTITY) $ ProxiedRelay sId v <$> validateRelay chain key
+            Just (Compatible v) -> liftEitherWith (const $ transportErr $ TEHandshake IDENTITY) $ ProxiedRelay sId v proxyAuth <$> validateRelay chain key
         r -> throwE $ unexpectedResponse r
   | otherwise = throwE $ PCETransportError TEVersion
   where
@@ -842,6 +842,7 @@ connectSMPProxiedRelay c@ProtocolClient {client_ = PClient {tcpConnectTimeout, t
 data ProxiedRelay = ProxiedRelay
   { prSessionId :: SessionId,
     prVersion :: VersionSMP,
+    prBasicAuth :: Maybe BasicAuth, -- auth is included here to allow reconnecting via the same proxy after NO_SESSION error
     prServerKey :: C.PublicKeyX25519
   }
 
@@ -902,7 +903,7 @@ proxySMPCommand ::
   SenderId ->
   Command 'Sender ->
   ExceptT SMPClientError IO (Either ProxyClientError ())
-proxySMPCommand c@ProtocolClient {thParams = proxyThParams, client_ = PClient {clientCorrId = g, tcpTimeout}} (ProxiedRelay sessionId v serverKey) spKey sId command = do
+proxySMPCommand c@ProtocolClient {thParams = proxyThParams, client_ = PClient {clientCorrId = g, tcpTimeout}} (ProxiedRelay sessionId v _ serverKey) spKey sId command = do
   -- prepare params
   let serverThAuth = (\ta -> ta {serverPeerPubKey = serverKey}) <$> thAuth proxyThParams
       serverThParams = smpTHParamsSetVersion v proxyThParams {sessionId, thAuth = serverThAuth}
diff --git a/tests/SMPProxyTests.hs b/tests/SMPProxyTests.hs
index 625dfbda7..7505ef977 100644
--- a/tests/SMPProxyTests.hs
+++ b/tests/SMPProxyTests.hs
@@ -34,7 +34,8 @@ import Simplex.Messaging.Client
 import qualified Simplex.Messaging.Crypto as C
 import Simplex.Messaging.Crypto.Ratchet (pattern PQSupportOn)
 import qualified Simplex.Messaging.Crypto.Ratchet as CR
-import Simplex.Messaging.Protocol as SMP
+import Simplex.Messaging.Protocol (EncRcvMsgBody (..), MsgBody, RcvMessage (..), SubscriptionMode (..), maxMessageLength, noMsgFlags)
+import qualified Simplex.Messaging.Protocol as SMP
 import Simplex.Messaging.Server.Env.STM (ServerConfig (..))
 import Simplex.Messaging.Transport
 import Simplex.Messaging.Util (bshow, tshow)
@@ -122,6 +123,8 @@ smpProxyTests = do
           agentViaProxyVersionError
         it "retries sending when destination or proxy relay is offline" $
           agentViaProxyRetryOffline
+        it "retries sending when destination relay session disconnects in proxy" $
+          agentViaProxyRetryNoSession
       describe "stress test 1k" $ do
         let deliver nAgents nMsgs = agentDeliverMessagesViaProxyConc (replicate nAgents [srv1]) (map bshow [1 :: Int .. nMsgs])
         it "2 agents, 250 messages" . oneServer $ deliver 2 250
@@ -157,7 +160,7 @@ deliverMessagesViaProxy proxyServ relayServ alg unsecuredMsgs securedMsgs = do
   -- prepare receiving queue
   (rPub, rPriv) <- atomically $ C.generateAuthKeyPair alg g
   (rdhPub, rdhPriv :: C.PrivateKeyX25519) <- atomically $ C.generateKeyPair g
-  QIK {rcvId, sndId, rcvPublicDhKey = srvDh} <- runExceptT' $ createSMPQueue rc (rPub, rPriv) rdhPub (Just "correct") SMSubscribe False
+  SMP.QIK {rcvId, sndId, rcvPublicDhKey = srvDh} <- runExceptT' $ createSMPQueue rc (rPub, rPriv) rdhPub (Just "correct") SMSubscribe False
   let dec = decryptMsgV3 $ C.dh' srvDh rdhPriv
   -- get proxy session
   sess0 <- runExceptT' $ connectSMPProxiedRelay pc relayServ (Just "correct")
@@ -374,18 +377,38 @@ agentViaProxyRetryOffline = do
     msgId = subtract baseId . fst
     servers srv = (initAgentServersProxy SPMAlways SPFProhibit) {smp = userServers [srv]}
 
+agentViaProxyRetryNoSession :: IO ()
+agentViaProxyRetryNoSession = do
+  let srv1 = SMPServer testHost testPort testKeyHash
+      srv2 = SMPServer testHost testPort2 testKeyHash
+  withAgent 1 agentCfg (servers srv1) testDB $ \a ->
+    withAgent 2 agentCfg (servers srv2) testDB2 $ \b -> do
+      withSmpServerConfigOn (transport @TLS) proxyCfg testPort $ \_ -> do
+        (aId, _) <- withServer2 $ \_ -> runRight $ makeConnection a b
+        nGet b =##> \case ("", "", DOWN _ [c]) -> c == aId; _ -> False
+        withServer2 $ \_ -> do
+          nGet b =##> \case ("", "", UP _ [c]) -> c == aId; _ -> False
+          -- to test retry in case of NO_SESSION error,
+          -- the client using server 1 as proxy and server 2 as destination
+          -- should be joining the connection, so the order is swapped here.
+          _ <- runRight $ makeConnection b a
+          pure ()
+  where
+    withServer2 = withSmpServerConfigOn (transport @TLS) proxyCfg {storeLogFile = Just testStoreLogFile2, storeMsgsFile = Just testStoreMsgsFile2} testPort2
+    servers srv = (initAgentServersProxy SPMAlways SPFProhibit) {smp = userServers [srv]}
+
 testNoProxy :: IO ()
 testNoProxy = do
   withSmpServerConfigOn (transport @TLS) cfg testPort2 $ \_ -> do
     testSMPClient_ "127.0.0.1" testPort2 proxyVRangeV8 $ \(th :: THandleSMP TLS 'TClient) -> do
-      (_, _, (_corrId, _entityId, reply)) <- sendRecv th (Nothing, "0", "", PRXY testSMPServer Nothing)
+      (_, _, (_corrId, _entityId, reply)) <- sendRecv th (Nothing, "0", "", SMP.PRXY testSMPServer Nothing)
       reply `shouldBe` Right (SMP.ERR $ SMP.PROXY SMP.BASIC_AUTH)
 
 testProxyAuth :: IO ()
 testProxyAuth = do
   withSmpServerConfigOn (transport @TLS) proxyCfgAuth testPort $ \_ -> do
     testSMPClient_ "127.0.0.1" testPort proxyVRangeV8 $ \(th :: THandleSMP TLS 'TClient) -> do
-      (_, _s, (_corrId, _entityId, reply)) <- sendRecv th (Nothing, "0", "", PRXY testSMPServer2 $ Just "wrong")
+      (_, _s, (_corrId, _entityId, reply)) <- sendRecv th (Nothing, "0", "", SMP.PRXY testSMPServer2 $ Just "wrong")
       reply `shouldBe` Right (SMP.ERR $ SMP.PROXY SMP.BASIC_AUTH)
   where
     proxyCfgAuth = proxyCfg {newQueueBasicAuth = Just "correct"}