diff --git a/src/Simplex/Messaging/Client.hs b/src/Simplex/Messaging/Client.hs
index 7a2eedeb9..d96078804 100644
--- a/src/Simplex/Messaging/Client.hs
+++ b/src/Simplex/Messaging/Client.hs
@@ -150,7 +150,7 @@ import Data.Int (Int64)
 import Data.List (find, isSuffixOf)
 import Data.List.NonEmpty (NonEmpty (..))
 import qualified Data.List.NonEmpty as L
-import Data.Maybe (catMaybes, fromMaybe)
+import Data.Maybe (catMaybes, fromMaybe, isJust)
 import Data.Text (Text)
 import qualified Data.Text as T
 import Data.Time.Clock (UTCTime (..), diffUTCTime, getCurrentTime)
@@ -442,9 +442,12 @@ defaultNetworkConfig =
 
 transportClientConfig :: NetworkConfig -> NetworkRequestMode -> TransportHost -> Bool -> Maybe [ALPN] -> TransportClientConfig
 transportClientConfig NetworkConfig {socksProxy, socksMode, tcpConnectTimeout, tcpKeepAlive, logTLSErrors} nm host useSNI clientALPN =
-  TransportClientConfig {socksProxy = useSocksProxy socksMode, tcpConnectTimeout = tOut, tcpKeepAlive, logTLSErrors, clientCredentials = Nothing, clientALPN, useSNI}
+  TransportClientConfig {socksProxy = socks, tcpConnectTimeout = tOut, tcpKeepAlive = keepAlive, logTLSErrors, clientCredentials = Nothing, clientALPN, useSNI}
   where
     tOut = netTimeoutInt tcpConnectTimeout nm
+    socks = useSocksProxy socksMode
+    -- with SOCKS proxy the socket is connected to the proxy, and a slow circuit should not fail the connection
+    keepAlive = (\ka -> if isJust socks then ka {unackedDataTimeout = Nothing} else ka) <$> tcpKeepAlive
     socksProxy' = (\(SocksProxyWithAuth _ proxy) -> proxy) <$> socksProxy
     useSocksProxy SMAlways = socksProxy'
     useSocksProxy SMOnion = case host of
diff --git a/src/Simplex/Messaging/Transport/KeepAlive.hs b/src/Simplex/Messaging/Transport/KeepAlive.hs
index 1d34a27f0..42059f22d 100644
--- a/src/Simplex/Messaging/Transport/KeepAlive.hs
+++ b/src/Simplex/Messaging/Transport/KeepAlive.hs
@@ -11,6 +11,7 @@ module Simplex.Messaging.Transport.KeepAlive
   ) where
 
 import qualified Data.Aeson.TH as J
+import Control.Monad (when)
 import Foreign.C (CInt (..))
 import Network.Socket
 import Simplex.Messaging.Parsers (defaultJSON)
@@ -18,16 +19,25 @@ import Simplex.Messaging.Parsers (defaultJSON)
 data KeepAliveOpts = KeepAliveOpts
   { keepIdle :: Int,
     keepIntvl :: Int,
-    keepCnt :: Int
+    keepCnt :: Int,
+    -- | A connection with unacknowledged data gets no keep-alive probes, so the OS fails it only when it
+    -- gives up retransmitting - ~15 minutes on Linux and Android. When this is set such a connection is
+    -- failed after the keep-alive detection time instead. Absent or False - the OS default.
+    unackedDataTimeout :: Maybe Bool
   }
   deriving (Eq, Show)
 
+-- seconds after which a connection with no response to the probes is reported as failed
+keepAliveDetectionTime :: KeepAliveOpts -> Int
+keepAliveDetectionTime KeepAliveOpts {keepIdle, keepIntvl, keepCnt} = keepIdle + keepIntvl * keepCnt
+
 defaultKeepAliveOpts :: KeepAliveOpts
 defaultKeepAliveOpts =
   KeepAliveOpts
     { keepIdle = 30,
       keepIntvl = 15,
-      keepCnt = 4
+      keepCnt = 4,
+      unackedDataTimeout = Nothing
     }
 
 _SOL_TCP :: CInt
@@ -53,8 +63,12 @@ _TCP_KEEPCNT = 16
 
 #if defined(darwin_HOST_OS)
 foreign import capi "netinet/tcp.h value TCP_KEEPALIVE" _TCP_KEEPIDLE :: CInt
+
+foreign import capi "netinet/tcp.h value TCP_RXT_CONNDROPTIME" _TCP_RXT_CONNDROPTIME :: CInt
 #else
 foreign import capi "netinet/tcp.h value TCP_KEEPIDLE" _TCP_KEEPIDLE :: CInt
+
+foreign import capi "netinet/tcp.h value TCP_USER_TIMEOUT" _TCP_USER_TIMEOUT :: CInt
 #endif
 
 foreign import capi "netinet/tcp.h value TCP_KEEPINTVL" _TCP_KEEPINTVL :: CInt
@@ -63,11 +77,22 @@ foreign import capi "netinet/tcp.h value TCP_KEEPCNT" _TCP_KEEPCNT :: CInt
 
 #endif
 
+-- | seconds
+setSocketUnackedDataTimeout :: Socket -> Int -> IO ()
+#if defined(mingw32_HOST_OS)
+setSocketUnackedDataTimeout _ _ = pure ()
+#elif defined(darwin_HOST_OS)
+setSocketUnackedDataTimeout sock = setSocketOption sock (SockOpt _SOL_TCP _TCP_RXT_CONNDROPTIME)
+#else
+setSocketUnackedDataTimeout sock t = setSocketOption sock (SockOpt _SOL_TCP _TCP_USER_TIMEOUT) (t * 1000) -- TCP_USER_TIMEOUT is in milliseconds
+#endif
+
 setSocketKeepAlive :: Socket -> KeepAliveOpts -> IO ()
-setSocketKeepAlive sock KeepAliveOpts {keepCnt, keepIdle, keepIntvl} = do
+setSocketKeepAlive sock ka@KeepAliveOpts {keepCnt, keepIdle, keepIntvl, unackedDataTimeout} = do
   setSocketOption sock KeepAlive 1
   setSocketOption sock (SockOpt _SOL_TCP _TCP_KEEPIDLE) keepIdle
   setSocketOption sock (SockOpt _SOL_TCP _TCP_KEEPINTVL) keepIntvl
   setSocketOption sock (SockOpt _SOL_TCP _TCP_KEEPCNT) keepCnt
+  when (unackedDataTimeout == Just True) $ setSocketUnackedDataTimeout sock $ keepAliveDetectionTime ka
 
 $(J.deriveJSON defaultJSON ''KeepAliveOpts)