diff --git a/ChangeLog.md b/ChangeLog.md
--- a/ChangeLog.md
+++ b/ChangeLog.md
@@ -1,3 +1,40 @@
+# Changelog for http-client-tls
+
+## 0.4.0
+
+* For MD5 hashes in Base16 format, depend on packages `cryptohash-md5` and
+  `base16` rather than `crypton` and `memory` (the latter is unmaintained).
+
+## 0.3.6.4
+
+* data-default-class -> data-default [#546](https://github.com/snoyberg/http-client/pull/546/files)
+
+## 0.3.6.3
+
+* catching up to tls 1.8.0 [#515](https://github.com/snoyberg/http-client/pull/515)
+
+## 0.3.6.2
+
+* Migrate to `crypton`
+
+## 0.3.6.1
+
+* [#482](https://github.com/snoyberg/http-client/issues/482):
+  Raise lower bound on `http-client` to fix build.
+
+## 0.3.6
+
+* Allow making requests to raw IPv6 hosts [#477](https://github.com/snoyberg/http-client/pull/477)
+
+## 0.3.5.3
+
+* Fix `newTlsManager` [#325](https://github.com/snoyberg/http-client/issues/325)
+
+## 0.3.5.2
+
+* [#289](https://github.com/snoyberg/http-client/issues/289):
+  Keep original `TLSSettings` when creating a `Manager` using `newTlsManagerWith`.
+
 ## 0.3.5.1
 
 * Also catch TLSError exceptions [#273](https://github.com/snoyberg/http-client/pull/273)
diff --git a/Network/HTTP/Client/TLS.hs b/Network/HTTP/Client/TLS.hs
--- a/Network/HTTP/Client/TLS.hs
+++ b/Network/HTTP/Client/TLS.hs
@@ -26,7 +26,7 @@
 import Control.Applicative ((<|>))
 import Control.Arrow (first)
 import System.Environment (getEnvironment)
-import Data.Default.Class
+import Data.Default
 import Network.HTTP.Client hiding (host, port)
 import Network.HTTP.Client.Internal hiding (host, port)
 import Control.Exception
@@ -41,9 +41,10 @@
 import qualified Data.CaseInsensitive as CI
 import Data.Maybe (fromMaybe, isJust)
 import Network.HTTP.Types (status401)
-import Crypto.Hash (hash, Digest, MD5)
+import qualified Crypto.Hash.MD5 as MD5
 import Control.Arrow ((***))
-import Data.ByteArray.Encoding (convertToBase, Base (Base16))
+import Data.Base16.Types (extractBase16)
+import Data.ByteString.Base16 (encodeBase16')
 import Data.Typeable (Typeable)
 import Control.Monad.Catch (MonadThrow, throwM)
 import qualified Data.Map as Map
@@ -91,18 +92,22 @@
     , managerRetryableException = \e ->
         case () of
             ()
+#if MIN_VERSION_tls(1,8,0)
+                | ((fromException e)::(Maybe TLS.TLSException))==Just (TLS.PostHandshake TLS.Error_EOF) -> True
+#else
                 | ((fromException e)::(Maybe TLS.TLSError))==Just TLS.Error_EOF -> True
+#endif
                 | otherwise -> managerRetryableException defaultManagerSettings e
     , managerWrapException = \req ->
         let wrapper se
               | Just (_ :: IOException)          <- fromException se = se'
               | Just (_ :: TLS.TLSException)     <- fromException se = se'
+#if !MIN_VERSION_tls(1,8,0)
               | Just (_ :: TLS.TLSError)         <- fromException se = se'
+#endif
               | Just (_ :: NC.LineTooLong)       <- fromException se = se'
-#if MIN_VERSION_connection(0,2,7)
               | Just (_ :: NC.HostNotResolved)   <- fromException se = se'
               | Just (_ :: NC.HostCannotConnect) <- fromException se = se'
-#endif
               | otherwise = se
               where
                 se' = toException $ HttpExceptionRequest req $ InternalException se
@@ -121,7 +126,7 @@
     context <- maybe NC.initConnectionContext return mcontext
     return $ \_ha host port -> bracketOnError
         (NC.connectTo context NC.ConnectionParams
-            { NC.connectionHostname = host
+            { NC.connectionHostname = strippedHostName host
             , NC.connectionPort = fromIntegral port
             , NC.connectionUseSecure = tls
             , NC.connectionUseSocks = sock
@@ -138,13 +143,13 @@
     context <- maybe NC.initConnectionContext return mcontext
     return $ \connstr checkConn serverName _ha host port -> bracketOnError
         (NC.connectTo context NC.ConnectionParams
-            { NC.connectionHostname = serverName
+            { NC.connectionHostname = strippedHostName serverName
             , NC.connectionPort = fromIntegral port
             , NC.connectionUseSecure = Nothing
             , NC.connectionUseSocks =
                 case sock of
                     Just _ -> error "Cannot use SOCKS and TLS proxying together"
-                    Nothing -> Just $ NC.OtherProxy host $ fromIntegral port
+                    Nothing -> Just $ NC.OtherProxy (strippedHostName host) $ fromIntegral port
             })
         NC.connectionClose
         $ \conn -> do
@@ -180,7 +185,16 @@
 --
 -- @since 0.3.4
 newTlsManager :: MonadIO m => m Manager
-newTlsManager = newTlsManagerWith defaultManagerSettings
+newTlsManager = liftIO $ do
+    env <- getEnvironment
+    let lenv = Map.fromList $ map (first $ T.toLower . T.pack) env
+        msocksHTTP = parseSocksSettings env lenv "http_proxy"
+        msocksHTTPS = parseSocksSettings env lenv "https_proxy"
+        settings = mkManagerSettingsContext' defaultManagerSettings (Just globalConnectionContext) def msocksHTTP msocksHTTPS
+        settings' = maybe id (const $ managerSetInsecureProxy proxyFromRequest) msocksHTTP
+                  $ maybe id (const $ managerSetSecureProxy proxyFromRequest) msocksHTTPS
+                    settings
+    newManager settings'
 
 -- | Load up a new TLS manager based upon specified settings,
 -- respecting proxy environment variables.
@@ -196,6 +210,14 @@
         settings' = maybe id (const $ managerSetInsecureProxy proxyFromRequest) msocksHTTP
                   $ maybe id (const $ managerSetSecureProxy proxyFromRequest) msocksHTTPS
                     settings
+                        -- We want to keep the original TLS settings that were
+                        -- passed in. Sadly they aren't available as a record
+                        -- field on `ManagerSettings`. So instead we grab the
+                        -- fields that depend on the TLS settings.
+                        -- https://github.com/snoyberg/http-client/issues/289
+                        { managerTlsConnection = managerTlsConnection set
+                        , managerTlsProxyConnection = managerTlsProxyConnection set
+                        }
     newManager settings'
 
 parseSocksSettings :: [(String, String)] -- ^ original environment
@@ -340,7 +362,7 @@
                 -- we always use no qop or qop=auth
                 ha2 = md5 $ S.concat [method req, ":", path req]
 
-                md5 bs = convertToBase Base16 (hash bs :: Digest MD5)
+                md5 = extractBase16 . encodeBase16' . MD5.hash
             key = "Authorization"
             val = S.concat
                 [ "Digest username=\""
diff --git a/bench/Bench.hs b/bench/Bench.hs
--- a/bench/Bench.hs
+++ b/bench/Bench.hs
@@ -1,6 +1,11 @@
+{-# LANGUAGE CPP #-}
 module Main where
 
-import Criterion.Main
+#if MIN_VERSION_gauge(0, 2, 0)
+import Gauge
+#else
+import Gauge.Main
+#endif
 import Network.HTTP.Client
 import Network.HTTP.Client.TLS
 
diff --git a/http-client-tls.cabal b/http-client-tls.cabal
--- a/http-client-tls.cabal
+++ b/http-client-tls.cabal
@@ -1,5 +1,5 @@
 name:                http-client-tls
-version:             0.3.5.1
+version:             0.4.0
 synopsis:            http-client backend using the connection package and tls library
 description:         Hackage documentation generation is not reliable. For up to date documentation, please see: <https://www.stackage.org/package/http-client-tls>.
 homepage:            https://github.com/snoyberg/http-client
@@ -16,18 +16,18 @@
 library
   exposed-modules:     Network.HTTP.Client.TLS
   other-extensions:    ScopedTypeVariables
-  build-depends:       base >= 4 && < 5
-                     , data-default-class
-                     , http-client >= 0.5.0
-                     , connection >= 0.2.5
+  build-depends:       base >= 4.10 && < 5
+                     , base16 >= 1.0
+                     , cryptohash-md5
+                     , data-default
+                     , http-client >= 0.7.11
+                     , crypton-connection
                      , network
-                     , tls >= 1.2
+                     , tls >= 2.1.2
                      , bytestring
                      , case-insensitive
                      , transformers
                      , http-types
-                     , cryptonite
-                     , memory
                      , exceptions
                      , containers
                      , text
@@ -45,6 +45,9 @@
                      , http-client
                      , http-client-tls
                      , http-types
+                     , crypton-connection
+                     , data-default
+                     , tls
 
 benchmark benchmark
   main-is:             Bench.hs
@@ -52,6 +55,6 @@
   hs-source-dirs:      bench
   default-language:    Haskell2010
   build-depends:       base
-                     , criterion
+                     , gauge
                      , http-client
                      , http-client-tls
diff --git a/test/Spec.hs b/test/Spec.hs
--- a/test/Spec.hs
+++ b/test/Spec.hs
@@ -1,12 +1,28 @@
+{-# LANGUAGE CPP #-}
 {-# LANGUAGE OverloadedStrings #-}
 import Test.Hspec
+import Network.Connection
 import Network.HTTP.Client
-import Network.HTTP.Client.TLS
+import Network.HTTP.Client.TLS hiding (tlsManagerSettings)
 import Network.HTTP.Types
 import Control.Monad (join)
+import Data.Default
+import qualified Network.TLS as TLS
 
 main :: IO ()
 main = hspec $ do
+    let tlsSettings = def
+    -- Since the release of v2.0.0 of the `tls` package , the default value of
+    -- the `supportedExtendedMainSecret` parameter `is `RequireEMS`, this means
+    -- that all the connections to a server not supporting TLS1.2+EMS will fail.
+    -- The badssl.com service does not yet support TLS1.2+EMS connections, so
+    -- let's switch to the value `AllowEMS`, ie: TLS1.2 conenctions without EMS.
+#if MIN_VERSION_crypton_connection(0,4,0)
+            {settingClientSupported = def {TLS.supportedExtendedMainSecret = TLS.AllowEMS}}
+#endif
+
+    let tlsManagerSettings = mkManagerSettings tlsSettings Nothing
+
     it "make a TLS connection" $ do
         manager <- newManager tlsManagerSettings
         withResponse "https://httpbin.org/status/418" manager $ \res ->
@@ -27,3 +43,45 @@
         join (applyDigestAuth "user" "passwd" "http://httpbin.org/" man)
             `shouldThrow` \(DigestAuthException _ _ det) ->
                 det == UnexpectedStatusCode
+
+    it "BadSSL: expired" $ do
+        manager <- newManager tlsManagerSettings
+        let action = withResponse "https://expired.badssl.com/" manager (const (return ()))
+        action `shouldThrow` anyException
+
+    it "BadSSL: self-signed" $ do
+        manager <- newManager tlsManagerSettings
+        let action = withResponse "https://self-signed.badssl.com/" manager (const (return ()))
+        action `shouldThrow` anyException
+
+    it "BadSSL: wrong.host" $ do
+        manager <- newManager tlsManagerSettings
+        let action = withResponse "https://wrong.host.badssl.com/" manager (const (return ()))
+        action `shouldThrow` anyException
+
+    it "BadSSL: we do have case-insensitivity though" $ do
+        manager <- newManager $ tlsManagerSettings
+        withResponse "https://BADSSL.COM" manager $ \res ->
+            responseStatus res `shouldBe` status200
+
+    -- https://github.com/snoyberg/http-client/issues/289
+    it "accepts TLS settings" $ do
+        let
+          tlsSettings' = tlsSettings
+            { settingDisableCertificateValidation = True
+            , settingDisableSession = False
+            , settingUseServerName = False
+            }
+          socketSettings = Nothing
+          managerSettings = mkManagerSettings tlsSettings' socketSettings
+        manager <- newTlsManagerWith managerSettings
+        let url = "https://wrong.host.badssl.com"
+        request <- parseRequest url
+        response <- httpNoBody request manager
+        responseStatus response `shouldBe` status200
+
+    it "global supports TLS" $ do
+        manager <- getGlobalManager
+        request <- parseRequest "https://httpbin.org"
+        response <- httpNoBody request manager
+        responseStatus response `shouldBe` status200
