diff --git a/Network/IRC/Client.hs b/Network/IRC/Client.hs
--- a/Network/IRC/Client.hs
+++ b/Network/IRC/Client.hs
@@ -136,7 +136,7 @@
   , _realname      = n
   , _password      = Nothing
   , _channels      = []
-  , _ctcpVer       = "irc-client-0.4.2.0"
+  , _ctcpVer       = "irc-client-0.4.2.1"
   , _eventHandlers = defaultEventHandlers
   , _ignore        = []
   }
diff --git a/Network/IRC/Client/Internal.hs b/Network/IRC/Client/Internal.hs
--- a/Network/IRC/Client/Internal.hs
+++ b/Network/IRC/Client/Internal.hs
@@ -12,14 +12,14 @@
 import Control.Concurrent         (forkIO)
 import Control.Concurrent.STM     (atomically, readTVar, retry, writeTVar)
 import Control.Exception          (SomeException, catch, throwIO)
-import Control.Monad              (unless)
+import Control.Monad              (unless, when)
 import Control.Monad.IO.Class     (MonadIO, liftIO)
 import Control.Monad.Trans.Reader (runReaderT)
 import Data.ByteString            (ByteString)
 import Data.Conduit               (Producer, Conduit, Consumer, (=$=), ($=), (=$), await, awaitForever, toProducer, yield)
 import Data.Conduit.TMChan        (closeTBMChan, isEmptyTBMChan, newTBMChanIO, sourceTBMChan, writeTBMChan)
 import Data.Text.Encoding         (decodeUtf8, encodeUtf8)
-import Data.Time.Clock            (NominalDiffTime, getCurrentTime)
+import Data.Time.Clock            (NominalDiffTime, addUTCTime, getCurrentTime)
 import Data.Time.Format           (formatTime)
 import Network.IRC.Conduit        (IrcEvent, IrcMessage, floodProtector, rawMessage, toByteString)
 import Network.IRC.Client.Types
@@ -208,11 +208,9 @@
       -- Set the state to @Disconnecting@
       liftIO . atomically $ writeTVar (_connState s) Disconnecting
 
-      -- Wait for all messages to be sent
+      -- Wait for all messages to be sent, or a minute has passed.
       queueS <- _sendqueue <$> connectionConfig
-      liftIO . atomically $ do
-        empty <- isEmptyTBMChan queueS
-        unless empty retry
+      timeout 60 . atomically $ isEmptyTBMChan queueS
 
       -- Then close the connection
       disconnectNow
@@ -228,3 +226,13 @@
 
   s <- ircState
   liftIO . atomically $ writeTVar (_connState s) Disconnected
+
+-- | Block until an action is successful or a timeout is reached.
+timeout :: MonadIO m => NominalDiffTime -> IO Bool -> m ()
+timeout dt check = liftIO $ do
+  finish <- addUTCTime dt <$> getCurrentTime
+  let wait = do
+        now  <- getCurrentTime
+        cond <- check
+        when (now < finish && not cond) wait
+  wait
diff --git a/irc-client.cabal b/irc-client.cabal
--- a/irc-client.cabal
+++ b/irc-client.cabal
@@ -10,7 +10,7 @@
 -- PVP summary:      +-+------- breaking API changes
 --                   | | +----- non-breaking API additions
 --                   | | | +--- code changes with no API change
-version:             0.4.2.0
+version:             0.4.2.1
 
 -- A short (one-line) description of the package.
 synopsis:            An IRC client library.
@@ -107,4 +107,4 @@
 source-repository this
   type:     git
   location: https://github.com/barrucadu/irc-client.git
-  tag:      0.4.2.0
+  tag:      0.4.2.1