diff --git a/changelog.d/5-internal/play-with-version-types b/changelog.d/5-internal/play-with-version-types
new file mode 100644
index 00000000000..df6311ba8b5
--- /dev/null
+++ b/changelog.d/5-internal/play-with-version-types
@@ -0,0 +1 @@
+Introduce VersionNumber newtype (see `/libs/wire-api/src/Wire/API/Routes/Version.hs` for explanation)
\ No newline at end of file
diff --git a/libs/wire-api/default.nix b/libs/wire-api/default.nix
index 8b7f20896ec..e502149190a 100644
--- a/libs/wire-api/default.nix
+++ b/libs/wire-api/default.nix
@@ -43,6 +43,8 @@
 , hex
 , hostname-validate
 , hscim
+, hspec
+, hspec-wai
 , http-api-data
 , http-media
 , http-types
@@ -87,6 +89,7 @@
 , tagged
 , tasty
 , tasty-expected-failure
+, tasty-hspec
 , tasty-hunit
 , tasty-quickcheck
 , text
@@ -223,6 +226,9 @@ mkDerivation {
     filepath
     hex
     hscim
+    hspec
+    hspec-wai
+    http-types
     imports
     iso3166-country-codes
     iso639
@@ -238,11 +244,13 @@ mkDerivation {
     saml2-web-sso
     schema-profunctor
     servant
+    servant-server
     servant-swagger-ui
     string-conversions
     swagger2
     tasty
     tasty-expected-failure
+    tasty-hspec
     tasty-hunit
     tasty-quickcheck
     text
@@ -253,6 +261,7 @@ mkDerivation {
     uri-bytestring
     uuid
     vector
+    wai
     wire-message-proto-lens
   ];
   license = lib.licenses.agpl3Only;
diff --git a/libs/wire-api/src/Wire/API/Routes/Version.hs b/libs/wire-api/src/Wire/API/Routes/Version.hs
index 364de313d53..87327d699d9 100644
--- a/libs/wire-api/src/Wire/API/Routes/Version.hs
+++ b/libs/wire-api/src/Wire/API/Routes/Version.hs
@@ -1,3 +1,4 @@
+{-# LANGUAGE GeneralizedNewtypeDeriving #-}
 {-# LANGUAGE StandaloneKindSignatures #-}
 {-# LANGUAGE TemplateHaskell #-}
 -- This file is part of the Wire Server implementation.
@@ -28,11 +29,9 @@ module Wire.API.Routes.Version
 
     -- * Version
     Version (..),
+    VersionNumber (..),
     supportedVersions,
     developmentVersions,
-    readVersionNumber,
-    mkVersion,
-    toPathComponent,
 
     -- * Servant combinators
     Until,
@@ -40,11 +39,13 @@ module Wire.API.Routes.Version
   )
 where
 
+import Control.Error (note)
 import Control.Lens ((?~))
 import Data.Aeson (FromJSON, ToJSON (..))
 import qualified Data.Aeson as Aeson
 import Data.Bifunctor
-import Data.ByteString.Conversion (ToByteString (builder))
+import qualified Data.Binary.Builder as Builder
+import Data.ByteString.Conversion (ToByteString (builder), toByteString')
 import qualified Data.ByteString.Lazy as LBS
 import Data.Domain
 import Data.Schema
@@ -57,52 +58,87 @@ import Servant
 import Servant.Swagger
 import Wire.API.Routes.Named
 import Wire.API.VersionInfo
+import Wire.Arbitrary (Arbitrary, GenericUniform (GenericUniform))
 
--- | Version of the public API. Check the documentation in the *docs* directory
--- for a checklist when adding a new version.
+-- | Version of the public API.  Serializes to `"v<n>"`.  See 'VersionNumber' below for one
+-- that serializes to `<n>`.  See `/libs/wire-api/test/unit/Test/Wire/API/Routes/Version.hs`
+-- for serialization rules.
+--
+-- If you add or remove versions from this type, make sure 'versionInt', 'supportedVersions',
+-- and 'developmentVersions' stay in sync; everything else here should keep working without
+-- change.  See also documentation in the *docs* directory.
 -- https://docs.wire.com/developer/developer/api-versioning.html#version-bump-checklist
 data Version = V0 | V1 | V2 | V3 | V4
-  deriving stock (Eq, Ord, Bounded, Enum, Show)
+  deriving stock (Eq, Ord, Bounded, Enum, Show, Generic)
   deriving (FromJSON, ToJSON) via (Schema Version)
+  deriving (Arbitrary) via (GenericUniform Version)
+
+-- | Manual enumeration of version integrals (the `<n>` in the constructor `V<n>`).
+--
+-- This is not the same as 'fromEnum': we will remove unsupported versions in the future,
+-- which will cause `<n>` and `fromEnum V<n>` to diverge.  `Enum` should not be understood as
+-- a bijection between meaningful integers and versions, but merely as a convenient way to say
+-- `allVersions = [minBound..]`.
+versionInt :: Integral i => Version -> i
+versionInt V0 = 0
+versionInt V1 = 1
+versionInt V2 = 2
+versionInt V3 = 3
+versionInt V4 = 4
+
+supportedVersions :: [Version]
+supportedVersions = [minBound .. V4]
+
+developmentVersions :: [Version]
+developmentVersions = [V4]
+
+----------------------------------------------------------------------
+
+versionText :: Version -> Text
+versionText = ("v" <>) . toUrlPiece . versionInt @Int
+
+versionByteString :: Version -> ByteString
+versionByteString = ("v" <>) . toByteString' . versionInt @Int
 
 instance ToSchema Version where
-  schema =
-    enum @Integer "Version" . mconcat $
-      [ element 0 V0,
-        element 1 V1,
-        element 2 V2,
-        element 3 V3,
-        element 4 V4
-      ]
-
-mkVersion :: Integer -> Maybe Version
-mkVersion n = case Aeson.fromJSON (Aeson.Number (fromIntegral n)) of
-  Aeson.Error _ -> Nothing
-  Aeson.Success v -> pure v
+  schema = enum @Text "Version" . mconcat $ (\v -> element (versionText v) v) <$> [minBound ..]
 
 instance FromHttpApiData Version where
-  parseHeader = first Text.pack . Aeson.eitherDecode . LBS.fromStrict
-  parseUrlPiece = parseHeader . Text.encodeUtf8
+  parseQueryParam v = note ("Unknown version: " <> v) $
+    getAlt $
+      flip foldMap [minBound ..] $ \s ->
+        guard (versionText s == v) $> s
 
 instance ToHttpApiData Version where
-  toHeader = LBS.toStrict . Aeson.encode
-  toUrlPiece = Text.decodeUtf8 . toHeader
+  toHeader = versionByteString
+  toUrlPiece = versionText
 
 instance ToByteString Version where
-  builder = toEncodedUrlPiece
+  builder = Builder.fromByteString . versionByteString
+
+-- | Wrapper around 'Version' that serializes to integers `<n>`, as needed in
+-- eg. `VersionInfo`.  See `/libs/wire-api/test/unit/Test/Wire/API/Routes/Version.hs` for
+-- serialization rules.
+newtype VersionNumber = VersionNumber {fromVersionNumber :: Version}
+  deriving stock (Eq, Ord, Show, Generic)
+  deriving newtype (Bounded, Enum)
+  deriving (FromJSON, ToJSON) via (Schema VersionNumber)
+  deriving (Arbitrary) via (GenericUniform Version)
+
+instance ToSchema VersionNumber where
+  schema =
+    enum @Integer "VersionNumber" . mconcat $ (\v -> element (versionInt v) (VersionNumber v)) <$> [minBound ..]
 
--- | `Version` as it appears in an URL path
---
--- >>> toPathComponent V1
--- "v1"
-toPathComponent :: Version -> ByteString
-toPathComponent v = "v" <> toHeader v
+instance FromHttpApiData VersionNumber where
+  parseHeader = first Text.pack . Aeson.eitherDecode . LBS.fromStrict
+  parseUrlPiece = parseHeader . Text.encodeUtf8
 
-supportedVersions :: [Version]
-supportedVersions = [minBound .. maxBound]
+instance ToHttpApiData VersionNumber where
+  toHeader = LBS.toStrict . Aeson.encode
+  toUrlPiece = Text.decodeUtf8 . toHeader
 
-developmentVersions :: [Version]
-developmentVersions = [V4]
+instance ToByteString VersionNumber where
+  builder = toEncodedUrlPiece
 
 -- | Information related to the public API version.
 --
@@ -111,8 +147,8 @@ developmentVersions = [V4]
 -- backend, in order to decide how to form request paths, and how to deal with
 -- federated backends and qualified user IDs.
 data VersionInfo = VersionInfo
-  { vinfoSupported :: [Version],
-    vinfoDevelopment :: [Version],
+  { vinfoSupported :: [VersionNumber],
+    vinfoDevelopment :: [VersionNumber],
     vinfoFederation :: Bool,
     vinfoDomain :: Domain
   }
@@ -130,7 +166,7 @@ instance ToSchema VersionInfo where
       example :: VersionInfo
       example =
         VersionInfo
-          { vinfoSupported = supportedVersions,
+          { vinfoSupported = VersionNumber <$> supportedVersions,
             vinfoDevelopment = [maxBound],
             vinfoFederation = False,
             vinfoDomain = Domain "example.com"
diff --git a/libs/wire-api/src/Wire/API/Routes/Version/Wai.hs b/libs/wire-api/src/Wire/API/Routes/Version/Wai.hs
index 545acdeae4d..50429098358 100644
--- a/libs/wire-api/src/Wire/API/Routes/Version/Wai.hs
+++ b/libs/wire-api/src/Wire/API/Routes/Version/Wai.hs
@@ -17,36 +17,50 @@
 
 module Wire.API.Routes.Version.Wai where
 
+import Control.Monad.Except (throwError)
 import Data.ByteString.Conversion
-import qualified Data.Text.Lazy as LText
+import Data.EitherR (fmapL)
+import Data.String.Conversions (cs)
+import qualified Data.Text as T
 import Imports
 import qualified Network.HTTP.Types as HTTP
 import Network.Wai
 import Network.Wai.Middleware.Rewrite
 import Network.Wai.Utilities.Error
 import Network.Wai.Utilities.Response
+import Web.HttpApiData (parseUrlPiece, toUrlPiece)
 import Wire.API.Routes.Version
 
 -- | Strip off version prefix. Return 404 if the version is not supported.
 versionMiddleware :: Set Version -> Middleware
 versionMiddleware disabledAPIVersions app req k = case parseVersion (removeVersionHeader req) of
-  Nothing -> app req k
-  Just (req', n) -> case mkVersion n of
-    Just v | v `notElem` disabledAPIVersions -> app (addVersionHeader v req') k
-    _ ->
-      k $
-        errorRs' $
-          mkError HTTP.status404 "unsupported-version" $
-            "Version " <> LText.pack (show n) <> " is not supported"
-
-parseVersion :: Request -> Maybe (Request, Integer)
+  Right (req', v) ->
+    if v `elem` disabledAPIVersions
+      then err (toUrlPiece v)
+      else app (addVersionHeader v req') k
+  Left (BadVersion v) -> err v
+  Left NoVersion -> app req k
+  where
+    err :: Text -> IO ResponseReceived
+    err v =
+      k . errorRs' . mkError HTTP.status404 "unsupported-version" $
+        "Version " <> cs v <> " is not supported"
+
+data ParseVersionError = NoVersion | BadVersion Text
+
+parseVersion :: Request -> Either ParseVersionError (Request, Version)
 parseVersion req = do
   (version, pinfo) <- case pathInfo req of
-    [] -> Nothing
+    [] -> throwError NoVersion
     (x : xs) -> pure (x, xs)
-  n <- readVersionNumber version
+  unless (looksLikeVersion version) $
+    throwError NoVersion
+  n <- fmapL (const $ BadVersion version) $ parseUrlPiece version
   pure (rewriteRequestPure (\(_, q) _ -> (pinfo, q)) req, n)
 
+looksLikeVersion :: Text -> Bool
+looksLikeVersion version = case T.splitAt 1 version of (h, t) -> h == "v" && T.all isDigit t
+
 removeVersionHeader :: Request -> Request
 removeVersionHeader req =
   req
diff --git a/libs/wire-api/src/Wire/API/VersionInfo.hs b/libs/wire-api/src/Wire/API/VersionInfo.hs
index 7809b0411f0..a50b3407cd2 100644
--- a/libs/wire-api/src/Wire/API/VersionInfo.hs
+++ b/libs/wire-api/src/Wire/API/VersionInfo.hs
@@ -20,7 +20,6 @@ module Wire.API.VersionInfo
     vinfoObjectSchema,
 
     -- * Version utilities
-    readVersionNumber,
     versionHeader,
     VersionHeader,
 
@@ -36,8 +35,6 @@ import qualified Data.CaseInsensitive as CI
 import Data.Metrics.Servant
 import Data.Schema
 import Data.Singletons
-import qualified Data.Text as Text
-import qualified Data.Text.Read as Text
 import GHC.TypeLits
 import Imports
 import qualified Network.Wai as Wai
@@ -51,13 +48,6 @@ import Wire.API.Routes.ClientAlgebra
 vinfoObjectSchema :: ValueSchema NamedSwaggerDoc v -> ObjectSchema SwaggerDoc [v]
 vinfoObjectSchema sch = field "supported" (array sch)
 
-readVersionNumber :: Text -> Maybe Integer
-readVersionNumber v = do
-  ('v', rest) <- Text.uncons v
-  case Text.decimal rest of
-    Right (n, "") -> pure n
-    _ -> Nothing
-
 type VersionHeader = "X-Wire-API-Version"
 
 versionHeader :: CI.CI ByteString
diff --git a/libs/wire-api/test/unit/Main.hs b/libs/wire-api/test/unit/Main.hs
index 7c3c3249c7e..3a0b5eb11a2 100644
--- a/libs/wire-api/test/unit/Main.hs
+++ b/libs/wire-api/test/unit/Main.hs
@@ -21,6 +21,7 @@ module Main
 where
 
 import Imports
+import System.IO.Unsafe (unsafePerformIO)
 import Test.Tasty
 import qualified Test.Wire.API.Call.Config as Call.Config
 import qualified Test.Wire.API.Conversation as Conversation
@@ -33,6 +34,7 @@ import qualified Test.Wire.API.Roundtrip.HttpApiData as Roundtrip.HttpApiData
 import qualified Test.Wire.API.Roundtrip.MLS as Roundtrip.MLS
 import qualified Test.Wire.API.Routes as Routes
 import qualified Test.Wire.API.Routes.Version as Routes.Version
+import qualified Test.Wire.API.Routes.Version.Wai as Routes.Version.Wai
 import qualified Test.Wire.API.Swagger as Swagger
 import qualified Test.Wire.API.Team.Export as Team.Export
 import qualified Test.Wire.API.Team.Member as Team.Member
@@ -63,5 +65,6 @@ main =
         Conversation.tests,
         MLS.tests,
         Routes.Version.tests,
+        unsafePerformIO Routes.Version.Wai.tests,
         RawJson.tests
       ]
diff --git a/libs/wire-api/test/unit/Test/Wire/API/Roundtrip/Aeson.hs b/libs/wire-api/test/unit/Test/Wire/API/Roundtrip/Aeson.hs
index 3586bb0a0b3..20348877470 100644
--- a/libs/wire-api/test/unit/Test/Wire/API/Roundtrip/Aeson.hs
+++ b/libs/wire-api/test/unit/Test/Wire/API/Roundtrip/Aeson.hs
@@ -47,6 +47,7 @@ import qualified Wire.API.Provider.Service as Provider.Service
 import qualified Wire.API.Provider.Service.Tag as Provider.Service.Tag
 import qualified Wire.API.Push.Token as Push.Token
 import qualified Wire.API.Routes.Internal.Galley.TeamsIntra as TeamsIntra
+import qualified Wire.API.Routes.Version as Routes.Version
 import qualified Wire.API.SystemSettings as SystemSettings
 import qualified Wire.API.Team as Team
 import qualified Wire.API.Team.Conversation as Team.Conversation
@@ -316,6 +317,8 @@ tests =
       testRoundTrip @User.Search.TeamContact,
       testRoundTrip @(Wrapped.Wrapped "some_int" Int),
       testRoundTrip @Conversation.Action.SomeConversationAction,
+      testRoundTrip @Routes.Version.Version,
+      testRoundTrip @Routes.Version.VersionNumber,
       testRoundTrip @TeamsIntra.GuardLegalholdPolicyConflicts,
       testRoundTrip @TeamsIntra.TeamStatus,
       testRoundTrip @TeamsIntra.TeamStatusUpdate,
diff --git a/libs/wire-api/test/unit/Test/Wire/API/Roundtrip/HttpApiData.hs b/libs/wire-api/test/unit/Test/Wire/API/Roundtrip/HttpApiData.hs
index 5ebf76a08e7..00ef20df73f 100644
--- a/libs/wire-api/test/unit/Test/Wire/API/Roundtrip/HttpApiData.hs
+++ b/libs/wire-api/test/unit/Test/Wire/API/Roundtrip/HttpApiData.hs
@@ -22,6 +22,7 @@ import Servant.API
 import qualified Test.Tasty as T
 import Test.Tasty.QuickCheck (Arbitrary, counterexample, testProperty, (===))
 import Type.Reflection (typeRep)
+import qualified Wire.API.Routes.Version
 import qualified Wire.API.User
 import qualified Wire.API.User.Search
 import qualified Wire.Arbitrary as Arbitrary ()
@@ -30,7 +31,9 @@ tests :: T.TestTree
 tests =
   T.localOption (T.Timeout (60 * 1000000) "60s") . T.testGroup "HttpApiData roundtrip tests" $
     [ testRoundTrip @Wire.API.User.InvitationCode,
-      testRoundTrip @Wire.API.User.Search.PagingState
+      testRoundTrip @Wire.API.User.Search.PagingState,
+      testRoundTrip @Wire.API.Routes.Version.Version,
+      testRoundTrip @Wire.API.Routes.Version.VersionNumber
     ]
 
 testRoundTrip ::
diff --git a/libs/wire-api/test/unit/Test/Wire/API/Routes/Version.hs b/libs/wire-api/test/unit/Test/Wire/API/Routes/Version.hs
index 9af4812e89f..6195c711f5c 100644
--- a/libs/wire-api/test/unit/Test/Wire/API/Routes/Version.hs
+++ b/libs/wire-api/test/unit/Test/Wire/API/Routes/Version.hs
@@ -1,22 +1,45 @@
 module Test.Wire.API.Routes.Version where
 
+import Data.Aeson as Aeson
+import Data.Binary.Builder
+import Data.ByteString.Conversion
+import Data.String.Conversions (cs)
 import Imports
-import qualified Test.Tasty as T
+import Servant.API
+import Test.Tasty
 import Test.Tasty.HUnit
 import Wire.API.Routes.Version
 
-tests :: T.TestTree
+{-# ANN tests ("HLint: ignore Functor law" :: String) #-}
+tests :: TestTree
 tests =
-  T.testGroup "Version" $
-    [ T.testGroup
-        "toPathComponent"
-        [testCase "serialise different versions" testToPathComponent]
+  testGroup
+    "Version always has the shape V<int>; serializations of Version and VersionNumber are `v<int>`, `<int>`, resp.  <int> is non-negative."
+    [ testCase "Version, show, 'v' prefix" $ do
+        nub (toLower . head . show <$> allVersions) @=? ['v'],
+      testCase "Version, show, int suffix" $ do
+        let expected = show $ (read @Int) . tail . show <$> allVersions
+        assertBool expected (isJust (Aeson.decode @[Int] (cs expected))),
+      testGroup "Version: all serializations are the same as `show`, up to string type" $ do
+        [ testCase "toByteString'" $ fmap toLower . show <$> allVersions @=? cs . toByteString' <$> allVersions,
+          testCase "encode" $ fmap toLower (show (show <$> allVersions)) @=? cs (encode allVersions), -- (`encode @Version` has extra double-quotes)
+          testCase "toUrlPiece" $ fmap toLower . show <$> allVersions @=? cs . toUrlPiece <$> allVersions,
+          testCase "toEncodedUrlPiece" $ fmap toLower . show <$> allVersions @=? cs . toLazyByteString . toEncodedUrlPiece <$> allVersions,
+          testCase "toHeader" $ fmap toLower . show <$> allVersions @=? cs . toHeader <$> allVersions,
+          testCase "toQueryParam" $ fmap toLower . show <$> allVersions @=? cs . toQueryParam <$> allVersions
+          ],
+      testGroup "VersionNumber: all serializations are the same as `tail . show . fromVersionNumber`, up to string type" $
+        [ testCase "toByteString'" $ tail . show . fromVersionNumber <$> allVersionNumbers @=? cs . toByteString' <$> allVersionNumbers,
+          testCase "encode" $ tail . show . fromVersionNumber <$> allVersionNumbers @=? cs . encode <$> allVersionNumbers,
+          testCase "toUrlPiece" $ tail . show . fromVersionNumber <$> allVersionNumbers @=? cs . toUrlPiece <$> allVersionNumbers,
+          testCase "toEncodedUrlPiece" $ tail . show . fromVersionNumber <$> allVersionNumbers @=? cs . toLazyByteString . toEncodedUrlPiece <$> allVersionNumbers,
+          testCase "toHeader" $ tail . show . fromVersionNumber <$> allVersionNumbers @=? cs . toHeader <$> allVersionNumbers,
+          testCase "toQueryParam" $ tail . show . fromVersionNumber <$> allVersionNumbers @=? cs . toQueryParam <$> allVersionNumbers
+        ]
     ]
 
-testToPathComponent :: Assertion
-testToPathComponent = do
-  "v0" @=? toPathComponent V0
-  "v1" @=? toPathComponent V1
-  "v2" @=? toPathComponent V2
-  "v3" @=? toPathComponent V3
-  "v4" @=? toPathComponent V4
+allVersions :: [Version]
+allVersions = [minBound ..]
+
+allVersionNumbers :: [VersionNumber]
+allVersionNumbers = [minBound ..]
diff --git a/libs/wire-api/test/unit/Test/Wire/API/Routes/Version/Wai.hs b/libs/wire-api/test/unit/Test/Wire/API/Routes/Version/Wai.hs
new file mode 100644
index 00000000000..e5107205da0
--- /dev/null
+++ b/libs/wire-api/test/unit/Test/Wire/API/Routes/Version/Wai.hs
@@ -0,0 +1,67 @@
+module Test.Wire.API.Routes.Version.Wai where
+
+import Data.Proxy
+import qualified Data.Set as Set
+import Data.String.Conversions
+import Data.Text as T
+import Imports
+import Network.HTTP.Types.Status (status200, status400)
+import Network.Wai
+import Servant.API
+import Servant.Server
+import Test.Hspec
+import Test.Hspec.Wai
+import Test.Hspec.Wai.Matcher
+import Test.Tasty
+import Test.Tasty.Hspec
+import Wire.API.Routes.Version
+import Wire.API.Routes.Version.Wai
+
+implicitVersion :: Text
+implicitVersion = "0"
+
+sndGoodVersion :: Text
+sndGoodVersion = "2"
+
+disabledVersion :: Text
+disabledVersion = T.filter isDigit . cs $ toHeader disabledVersionTyped
+
+disabledVersionTyped :: Version
+disabledVersionTyped = V3
+
+unknownVersion :: Text
+unknownVersion = "100"
+
+tests :: IO TestTree
+tests =
+  testSpec "versionMiddleware" . with testApp $ do
+    mkTest Nothing Nothing ("good", 200)
+    mkTest Nothing (Just implicitVersion) ("mismatch: (Nothing,Just 0)", 400)
+    mkTest Nothing (Just sndGoodVersion) ("mismatch: (Nothing,Just 2)", 400)
+    mkTest (Just implicitVersion) (Just implicitVersion) ("good", 200)
+    mkTest (Just sndGoodVersion) (Just sndGoodVersion) ("good", 200)
+    mkTest (Just disabledVersion) (Just disabledVersion) (errmsg disabledVersion, 404)
+    mkTest (Just unknownVersion) (Just unknownVersion) (errmsg unknownVersion, 404)
+  where
+    errmsg v = "{\"code\":404,\"label\":\"unsupported-version\",\"message\":\"Version v" <> cs v <> " is not supported\"}"
+
+mkTest :: Maybe Text -> Maybe Text -> (LByteString, Int) -> SpecWith (st, Application)
+mkTest mv1 mv2 (msg, status) =
+  it ("GET " <> cs path <> " => " <> show (msg, status)) $ do
+    get path `shouldRespondWith` ResponseMatcher status [] (bodyEquals msg)
+  where
+    path :: ByteString
+    path = cs $ maybe "" ("/v" <>) mv1 <> "/check-version" <> maybe "" ("?version=" <>) mv2
+
+type TestAPI = "check-version" :> QueryParam "version" Int :> Raw
+
+testApp :: IO Application
+testApp = pure $ versionMiddleware (Set.singleton disabledVersionTyped) (serve (Proxy @TestAPI) testHandler)
+
+testHandler :: Server TestAPI
+testHandler mVersionNumber = Tagged $ \req cont ->
+  cont $
+    let headerVersion = lookup "X-Wire-API-Version" (requestHeaders req)
+     in if headerVersion == (cs . show <$> mVersionNumber)
+          then responseLBS status200 [] "good"
+          else responseLBS status400 [] (cs $ "mismatch: " <> show (headerVersion, mVersionNumber))
diff --git a/libs/wire-api/wire-api.cabal b/libs/wire-api/wire-api.cabal
index 8571f041ddf..2428be72dcb 100644
--- a/libs/wire-api/wire-api.cabal
+++ b/libs/wire-api/wire-api.cabal
@@ -660,6 +660,7 @@ test-suite wire-api-tests
     Test.Wire.API.Roundtrip.MLS
     Test.Wire.API.Routes
     Test.Wire.API.Routes.Version
+    Test.Wire.API.Routes.Version.Wai
     Test.Wire.API.Swagger
     Test.Wire.API.Team.Export
     Test.Wire.API.Team.Member
@@ -734,6 +735,9 @@ test-suite wire-api-tests
     , filepath
     , hex
     , hscim
+    , hspec
+    , hspec-wai
+    , http-types
     , imports
     , iso3166-country-codes
     , iso639
@@ -749,11 +753,13 @@ test-suite wire-api-tests
     , saml2-web-sso
     , schema-profunctor
     , servant
+    , servant-server
     , servant-swagger-ui
     , string-conversions
     , swagger2
     , tasty
     , tasty-expected-failure
+    , tasty-hspec
     , tasty-hunit
     , tasty-quickcheck
     , text
@@ -764,6 +770,7 @@ test-suite wire-api-tests
     , uri-bytestring
     , uuid
     , vector
+    , wai
     , wire-api
     , wire-message-proto-lens
 
diff --git a/nix/wire-server.nix b/nix/wire-server.nix
index 8fc1b22edd1..0077c4dac96 100644
--- a/nix/wire-server.nix
+++ b/nix/wire-server.nix
@@ -373,7 +373,7 @@ in
       pkgs.netcat
       pkgs.niv
       (pkgs.python3.withPackages
-        (ps: with ps; [ pyyaml ]))
+        (ps: with ps; [ pyyaml requests ]))
       pkgs.rsync
       pkgs.wget
       pkgs.yq
diff --git a/services/brig/src/Brig/API/Public/Swagger.hs b/services/brig/src/Brig/API/Public/Swagger.hs
index 0e75164817a..514a44c47fa 100644
--- a/services/brig/src/Brig/API/Public/Swagger.hs
+++ b/services/brig/src/Brig/API/Public/Swagger.hs
@@ -60,7 +60,7 @@ pregenSwagger :: Version -> Q Exp
 pregenSwagger v =
   embedLazyByteString
     =<< makeRelativeToProject
-      ("docs/swagger-v" <> T.unpack (toUrlPiece v) <> ".json")
+      ("docs/swagger-v" <> T.unpack (toUrlPiece (VersionNumber v)) <> ".json")
 
 swaggerPregenUIServer :: LByteString -> Server SwaggerDocsAPIBase
 swaggerPregenUIServer =
diff --git a/services/brig/src/Brig/Effects/GalleyProvider/RPC.hs b/services/brig/src/Brig/Effects/GalleyProvider/RPC.hs
index 65ee53fead4..f028516bf38 100644
--- a/services/brig/src/Brig/Effects/GalleyProvider/RPC.hs
+++ b/services/brig/src/Brig/Effects/GalleyProvider/RPC.hs
@@ -99,7 +99,7 @@ createSelfConv u = do
   void $ ServiceRPC.request @'Galley POST req
   where
     req =
-      paths ["v" <> toHeader (maxBound :: Version), "conversations", "self"]
+      paths [toHeader (maxBound :: Version), "conversations", "self"]
         . zUser u
         . expect2xx
 
@@ -125,7 +125,7 @@ getConv usr lcnv = do
   where
     req =
       paths
-        [ "v" <> toHeader (maxBound :: Version),
+        [ toHeader (maxBound :: Version),
           "conversations",
           toByteString' (tDomain lcnv),
           toByteString' (tUnqualified lcnv)
@@ -155,7 +155,7 @@ getTeamConv usr tid cnv = do
   where
     req =
       paths
-        [ "v" <> toHeader (maxBound :: Version),
+        [ toHeader (maxBound :: Version),
           "teams",
           toByteString' tid,
           "conversations",
diff --git a/services/brig/src/Brig/Version.hs b/services/brig/src/Brig/Version.hs
index acf7603d76b..f3d6a5ca89e 100644
--- a/services/brig/src/Brig/Version.hs
+++ b/services/brig/src/Brig/Version.hs
@@ -40,8 +40,8 @@ versionAPI = Named $ do
         | otherwise = Set.difference allVersions devVersions
   pure $
     VersionInfo
-      { vinfoSupported = toList supported,
-        vinfoDevelopment = toList devVersions,
+      { vinfoSupported = VersionNumber <$> toList supported,
+        vinfoDevelopment = VersionNumber <$> toList devVersions,
         vinfoFederation = isJust fed,
         vinfoDomain = dom
       }
diff --git a/services/brig/test/integration/API/Version.hs b/services/brig/test/integration/API/Version.hs
index 07e52638ad3..1315d356ec9 100644
--- a/services/brig/test/integration/API/Version.hs
+++ b/services/brig/test/integration/API/Version.hs
@@ -53,7 +53,7 @@ testVersion brig = do
       =<< get (brig . path "/api-version")
         <!! const 200 === statusCode
   liftIO $
-    vinfoSupported vinfo @?= supportedVersions \\ developmentVersions
+    (fromVersionNumber <$> vinfoSupported vinfo) @?= supportedVersions \\ developmentVersions
 
 testVersionV1 :: Brig -> Http ()
 testVersionV1 brig = do
@@ -62,7 +62,7 @@ testVersionV1 brig = do
       =<< get (apiVersion "v1" . brig . path "api-version")
         <!! const 200 === statusCode
   liftIO $
-    vinfoSupported vinfo @?= supportedVersions \\ developmentVersions
+    (fromVersionNumber <$> vinfoSupported vinfo) @?= supportedVersions \\ developmentVersions
 
 testDevVersion :: Opts -> Brig -> Http ()
 testDevVersion opts brig = withSettingsOverrides
@@ -73,7 +73,7 @@ testDevVersion opts brig = withSettingsOverrides
         =<< get (brig . path "/api-version")
           <!! const 200 === statusCode
     liftIO $
-      vinfoSupported vinfo @?= supportedVersions
+      (fromVersionNumber <$> vinfoSupported vinfo) @?= supportedVersions
 
 testUnsupportedVersion :: Brig -> Http ()
 testUnsupportedVersion brig = do
@@ -127,7 +127,7 @@ testDisabledVersionIsUnsupported opts brig = do
 testVersionDisabledSupportedVersion :: Opts -> Brig -> Http ()
 testVersionDisabledSupportedVersion opts brig = do
   vinfo <- getVersionInfo brig
-  liftIO $ filter (== V2) (vinfoSupported vinfo) @?= [V2]
+  liftIO $ filter (== VersionNumber V2) (vinfoSupported vinfo) @?= [VersionNumber V2]
   disabledVersionIsNotAdvertised opts brig V2
 
 testVersionDisabledDevelopmentVersion :: Opts -> Brig -> Http ()
@@ -135,7 +135,7 @@ testVersionDisabledDevelopmentVersion opts brig = do
   vinfo <- getVersionInfo brig
   for_ (listToMaybe (vinfoDevelopment vinfo)) $ \devVersion -> do
     liftIO $ filter (== devVersion) (vinfoDevelopment vinfo) @?= [devVersion]
-    disabledVersionIsNotAdvertised opts brig devVersion
+    disabledVersionIsNotAdvertised opts brig (fromVersionNumber devVersion)
 
 disabledVersionIsNotAdvertised :: Opts -> Brig -> Version -> Http ()
 disabledVersionIsNotAdvertised opts brig version =
@@ -147,8 +147,8 @@ disabledVersionIsNotAdvertised opts brig version =
     )
     $ do
       vinfo <- getVersionInfo brig
-      liftIO $ filter (== version) (vinfoSupported vinfo) @?= []
-      liftIO $ filter (== version) (vinfoDevelopment vinfo) @?= []
+      liftIO $ filter (== VersionNumber version) (vinfoSupported vinfo) @?= []
+      liftIO $ filter (== VersionNumber version) (vinfoDevelopment vinfo) @?= []
 
 getVersionInfo ::
   (MonadIO m, MonadCatch m, MonadHttp m, HasCallStack) =>
diff --git a/services/brig/test/integration/Main.hs b/services/brig/test/integration/Main.hs
index 90b64986f4a..ad1d6a02d69 100644
--- a/services/brig/test/integration/Main.hs
+++ b/services/brig/test/integration/Main.hs
@@ -192,7 +192,7 @@ runTests iConf brigOpts otherArgs = do
     mkVersionedRequest endpoint = addPrefix . mkRequest endpoint
 
     addPrefix :: Request -> Request
-    addPrefix r = r {HTTP.path = "v" <> toHeader latestVersion <> "/" <> removeSlash (HTTP.path r)}
+    addPrefix r = r {HTTP.path = toHeader latestVersion <> "/" <> removeSlash (HTTP.path r)}
       where
         removeSlash s = case B8.uncons s of
           Just ('/', s') -> s'
diff --git a/services/cargohold/test/integration/TestSetup.hs b/services/cargohold/test/integration/TestSetup.hs
index 7b494caa43a..759c760a698 100644
--- a/services/cargohold/test/integration/TestSetup.hs
+++ b/services/cargohold/test/integration/TestSetup.hs
@@ -115,7 +115,7 @@ unversioned r =
 viewCargohold :: TestM Cargohold
 viewCargohold =
   fmap
-    (apiVersion ("v" <> toHeader latestVersion) .)
+    (apiVersion (toHeader latestVersion) .)
     viewUnversionedCargohold
   where
     latestVersion :: Version
diff --git a/services/galley/test/integration/API/Util.hs b/services/galley/test/integration/API/Util.hs
index ade69830f11..77bb1f65a70 100644
--- a/services/galley/test/integration/API/Util.hs
+++ b/services/galley/test/integration/API/Util.hs
@@ -150,7 +150,7 @@ addPrefix :: Request -> Request
 addPrefix = addPrefixAtVersion maxBound
 
 addPrefixAtVersion :: Version -> Request -> Request
-addPrefixAtVersion v r = r {HTTP.path = "v" <> toHeader v <> "/" <> removeSlash (HTTP.path r)}
+addPrefixAtVersion v r = r {HTTP.path = toHeader v <> "/" <> removeSlash (HTTP.path r)}
   where
     removeSlash s = case B8.uncons s of
       Just ('/', s') -> s'
diff --git a/services/run-services b/services/run-services
index 9fdbf894e6e..1cbd415f36f 100755
--- a/services/run-services
+++ b/services/run-services
@@ -10,17 +10,17 @@ import shutil
 import socket
 import subprocess
 import yaml
-import urllib.request
-import urllib.error
 import sys
 import tempfile
 import time
 import traceback
 import threading
+import requests
 
 @dataclass
 class SpawnFailException(Exception):
     failed_instances: object
+    failing_status_responses: object
 
 class Colors:
     GREEN = "\x1b[38;5;10m"
@@ -107,6 +107,18 @@ class Nginz:
         if shutil.which("nginx") is None:
             raise Exception("nginx not found")
 
+@dataclass
+class StatusResponse:
+    http_response: object = None
+    good_status: list[int] = None
+
+    def __bool__(self):
+        if self.http_response is None:
+            return False
+        else:
+            return self.http_response.status_code in self.good_status
+
+
 @dataclass(frozen=True)
 class Instance:
     service: Service
@@ -122,9 +134,9 @@ class Instance:
         if not self.service.check_status:
             return True
         try:
-            with urllib.request.urlopen(f"http://localhost:{self.port}/i/status") as resp:
-                return resp.status in [200, 204]
-        except urllib.error.URLError:
+            resp = requests.get(f"http://localhost:{self.port}/i/status")
+            return StatusResponse(resp, [200, 204])
+        except Exception as e:
             return False
 
     def spawn(self, service_map, environment, suffix, domain, backend_name):
@@ -323,6 +335,9 @@ def start_backend(services, suffix, domain, backend_name):
     # check instances
     to_be_checked = [instance for instance in instances
                      if instance.exception is None]
+
+    failing_status_responses = {}
+
     start_time = time.time()
     while to_be_checked:
         if time.time() - start_time >= 5:
@@ -333,8 +348,10 @@ def start_backend(services, suffix, domain, backend_name):
         to_be_checked_again = set()
         for instance in to_be_checked:
             try:
-                if not instance.check_status():
+                status = instance.check_status()
+                if not status:
                     to_be_checked_again.add(instance)
+                    failing_status_responses[instance] = status
             except Exception as e:
                 failed_instances.append(replace(instance, exception=e))
 
@@ -346,7 +363,7 @@ def start_backend(services, suffix, domain, backend_name):
 
     if failed_instances:
         cleanup_instances(instances)
-        raise SpawnFailException(failed_instances)
+        raise SpawnFailException(failed_instances, failing_status_responses)
 
     return instances
 
@@ -439,5 +456,10 @@ if __name__ == '__main__':
         for instance in e.failed_instances:
             print(f"{instance.service.name} at port {instance.port}" +
                  (f" ({instance.exception})" if instance.exception else ""))
+
+        for instance, status in e.failing_status_responses.items():
+            if isinstance(status, StatusResponse):
+                print(f"{instance.service.name} responded with status " +
+                      "{status.http_response.status_code} and body:\n " + status.http_response.text)
     finally:
         cleanup_instances(instances)
diff --git a/tools/stern/src/Stern/Intra.hs b/tools/stern/src/Stern/Intra.hs
index fe9429062da..6c80801e33c 100644
--- a/tools/stern/src/Stern/Intra.hs
+++ b/tools/stern/src/Stern/Intra.hs
@@ -89,6 +89,7 @@ import Imports
 import Network.HTTP.Types.Method
 import Network.HTTP.Types.Status hiding (statusCode)
 import Network.Wai.Utilities (Error (..), mkError)
+import Servant.API (toUrlPiece)
 import Stern.App
 import Stern.Types
 import System.Logger.Class hiding (Error, name, (.=))
@@ -120,10 +121,10 @@ backendApiVersion :: Version
 backendApiVersion = V2
 
 path :: ByteString -> Request -> Request
-path = Bilge.path . ((toPathComponent backendApiVersion <> "/") <>)
+path = Bilge.path . ((cs (toUrlPiece backendApiVersion) <> "/") <>)
 
 paths :: [ByteString] -> Request -> Request
-paths = Bilge.paths . (toPathComponent backendApiVersion :)
+paths = Bilge.paths . (cs (toUrlPiece backendApiVersion) :)
 
 -------------------------------------------------------------------------------