diff --git a/ChangeLog.md b/ChangeLog.md
--- a/ChangeLog.md
+++ b/ChangeLog.md
@@ -1,3 +1,7 @@
+## 0.4.24
+
+* Use a new `TlsExceptionHostPort` exception to indicate the host and port of the server we were trying to connect to when a TLS exception occurred. See [commercialhaskell/stack#1010](https://github.com/commercialhaskell/stack/issues/1010)
+
 ## 0.4.23
 
 * Case insensitive cookie domains [#158](https://github.com/snoyberg/http-client/issues/158)
diff --git a/Network/HTTP/Client/Core.hs b/Network/HTTP/Client/Core.hs
--- a/Network/HTTP/Client/Core.hs
+++ b/Network/HTTP/Client/Core.hs
@@ -146,13 +146,16 @@
 --
 -- Since 0.1.0
 responseOpen :: Request -> Manager -> IO (Response BodyReader)
-responseOpen req0 manager = mWrapIOException manager $ do
+responseOpen req0 manager = handle addTlsHostPort $ mWrapIOException manager $ do
     res <-
         if redirectCount req0 == 0
             then httpRaw req0 manager
             else go (redirectCount req0) req0
     maybe (return res) throwIO =<< applyCheckStatus req0 (checkStatus req0) res
   where
+    addTlsHostPort (TlsException e) = throwIO $ TlsExceptionHostPort e (host req0) (port req0)
+    addTlsHostPort e = throwIO e
+
     go count req' = httpRedirect
       count
       (\req -> do
diff --git a/Network/HTTP/Client/Types.hs b/Network/HTTP/Client/Types.hs
--- a/Network/HTTP/Client/Types.hs
+++ b/Network/HTTP/Client/Types.hs
@@ -133,6 +133,10 @@
                    -- and @transfer-encoding: chunked@ are used. Since 0.4.8.
                    --
                    -- Since 0.4.11 this exception isn't thrown anymore.
+                   | TlsExceptionHostPort SomeException S.ByteString Int
+                   -- ^ TLS exception, together with the host and port
+                   --
+                   -- @since 0.4.24
     deriving (Show, T.Typeable)
 instance Exception HttpException
 
diff --git a/http-client.cabal b/http-client.cabal
--- a/http-client.cabal
+++ b/http-client.cabal
@@ -1,5 +1,5 @@
 name:                http-client
-version:             0.4.23
+version:             0.4.24
 synopsis:            An HTTP client engine, intended as a base layer for more user-friendly packages.
 description:         Hackage documentation generation is not reliable. For up to date documentation, please see: <http://www.stackage.org/package/http-client>.
 homepage:            https://github.com/snoyberg/http-client