diff --git a/Happstack/Server/Helpers.hs b/Happstack/Server/Helpers.hs
--- a/Happstack/Server/Helpers.hs
+++ b/Happstack/Server/Helpers.hs
@@ -2,7 +2,8 @@
 module Happstack.Server.Helpers
     ( smartserver, exactdir, smartserver',getData',vhosts,vhost
     ) where
-
+import qualified Control.Exception as E
+import Data.IORef
 import Happstack.Server
 import Happstack.State
 import System.Environment
@@ -12,6 +13,8 @@
 import Debug.Trace.Helpers
 import Data.Maybe (fromMaybe)
 import qualified Data.ByteString.Char8 as B
+import System.Exit
+
 -- run the happs server on some port
 -- include cookie fix, various other enhancements that make things simpler
 smartserver' :: (Methods st, Component st, ToMessage b, Monad m, Functor m) => 
@@ -23,19 +26,33 @@
       control <- startSystemState stateProxy -- start the HAppS state system
 
       putStrLn . ( "happs state started" ++ ) =<< time
-      tid <- forkIO $ simpleHTTP' f conf handler
-      putStrLn . ( ( "simpleHttp started on port " ++ (show . port $ conf) ++ "\n" ++
+      
+      -- if the web server throws an error within 3 seconds, exit app gracefully (is there a better way to handle this?)
+      (webserverTid,result) <- catchStartupErrorInForkIO (simpleHTTP' f conf handler) 3
+      case result of
+        Left e -> do putStrLn $ "smartserver' couldn't start http server: " ++ (show e) 
+                     stateShutdown control 
+                     exitWith $ ExitFailure 0
+        _ -> putStrLn . ( ( "simpleHttp started on port " ++ (show . port $ conf) ++ "\n" ++
                  "shut down with ctrl-c" ) ++) =<< time
       waitForTermination
-      killThread tid
+      killThread webserverTid
+      stateShutdown control
+
+time = return . ("\ntime: " ++ ) . show  =<< getClockTime
+
+stateShutdown control = do
+
+
       putStrLn . ( "creating checkpoint: " ++ ) =<< time
       createCheckpoint control
 
       putStrLn .  ( "shutting down system: " ++ ) =<< time
       shutdownSystem control 
       putStrLn .  ( "exiting: " ++ ) =<< time
-         where time = return . ("\ntime: " ++ ) . show  =<< getClockTime
+  
 
+
 smartserver :: (Methods st, Component st, ToMessage a) =>
                Conf -> ServerPartT IO a -> Proxy st -> IO ()
 smartserver = smartserver' id
@@ -67,3 +84,15 @@
   (d :: String) <- (B.unpack . fromMaybe (error "Happstack.Helpers.Server.vhost, no host header")) `liftM` getHeaderM "host"
   guardRq $ \rq -> (d,p) == vh
   sp
+
+{-| If a forked IO action throws an exception within a certain amount of time, return the exception along with the threadId.
+    wait time needs to be long enough for the exception to arise, so when in doubt, err on the side of longer wait time
+-}
+catchStartupErrorInForkIO :: IO () -> Int -> IO (ThreadId, Either E.SomeException ())
+catchStartupErrorInForkIO ioAction waitSeconds = do
+  eIOref <- newIORef $ Right ()
+  tid <- forkIO $ ioAction `E.catch` (\e -> writeIORef eIOref (Left e))
+  threadDelay $ waitSeconds * (10^6)
+  new <- readIORef eIOref
+  return (tid,new)
+
diff --git a/happstack-helpers.cabal b/happstack-helpers.cabal
--- a/happstack-helpers.cabal
+++ b/happstack-helpers.cabal
@@ -1,5 +1,5 @@
 Name: happstack-helpers
-Version: 0.45
+Version: 0.46
 License: BSD3
 License-file: bsd3.txt
 Description: Functions I found I was using repeatedly when programming Happstack based web-apps.