diff --git a/app/ghcup/GHCup/OptParse/Upgrade.hs b/app/ghcup/GHCup/OptParse/Upgrade.hs
index 8849700..1b71c78 100644
--- a/app/ghcup/GHCup/OptParse/Upgrade.hs
+++ b/app/ghcup/GHCup/OptParse/Upgrade.hs
@@ -50,7 +50,7 @@ import Data.Versions         hiding (str)
 data UpgradeOpts = UpgradeInplace
                  | UpgradeAt FilePath
                  | UpgradeGHCupDir
-                 deriving Show
+                 deriving (Eq, Show)
 
 
 
diff --git a/ghcup.cabal b/ghcup.cabal
index c9672a4..c7b9d8b 100644
--- a/ghcup.cabal
+++ b/ghcup.cabal
@@ -425,6 +425,7 @@ test-suite ghcup-optparse-test
     UnsetTest
     RmTest
     ListTest
+    UpgradeTest
   default-language: Haskell2010
   ghc-options: -Wall
   build-depends: base, ghcup, ghcup-optparse, tasty, tasty-hunit, optparse-applicative, versions, text, uri-bytestring
diff --git a/test/optparse-test/Main.hs b/test/optparse-test/Main.hs
index 8bacfb2..c15743a 100644
--- a/test/optparse-test/Main.hs
+++ b/test/optparse-test/Main.hs
@@ -9,6 +9,7 @@ import qualified InstallTest
 import qualified UnsetTest
 import qualified RmTest
 import qualified ListTest
+import qualified UpgradeTest
 
 main :: IO ()
 main = defaultMain $ testGroup "ghcup"
@@ -20,4 +21,5 @@ main = defaultMain $ testGroup "ghcup"
   , UnsetTest.unsetTests
   , RmTest.rmTests
   , ListTest.listTests
+  , UpgradeTest.upgradeTests
   ]
diff --git a/test/optparse-test/UpgradeTest.hs b/test/optparse-test/UpgradeTest.hs
new file mode 100644
index 0000000..f54d2be
--- /dev/null
+++ b/test/optparse-test/UpgradeTest.hs
@@ -0,0 +1,38 @@
+{-# LANGUAGE TupleSections #-}
+
+module UpgradeTest where
+
+import Test.Tasty
+import GHCup.OptParse
+import Utils
+
+
+upgradeTests :: TestTree
+upgradeTests = buildTestTree upgradeParseWith ("upgrade", upgradeCheckList)
+
+type FullUpgradeOpts =
+  ( UpgradeOpts
+  , Bool -- ^Force update
+  , Bool -- ^Fails after upgrading if the upgraded ghcup binary is shadowed by something else in PATH (useful for CI)
+  )
+
+mkDefaultOptions :: UpgradeOpts -> FullUpgradeOpts
+mkDefaultOptions = (, False, False)
+
+upgradeCheckList :: [(String, FullUpgradeOpts)]
+upgradeCheckList =
+  [ ("upgrade", mkDefaultOptions UpgradeGHCupDir)
+  , ("upgrade -f", (UpgradeGHCupDir, True, False))
+  , ("upgrade --force", (UpgradeGHCupDir, True, False))
+  , ("upgrade --fail-if-shadowed", (UpgradeGHCupDir, False, True))
+  , ("upgrade -i", mkDefaultOptions UpgradeInplace)
+  , ("upgrade --inplace", mkDefaultOptions UpgradeInplace)
+  , ("upgrade -t ~", mkDefaultOptions $ UpgradeAt "~")
+  , ("upgrade --target ~", mkDefaultOptions $ UpgradeAt "~")
+  , ("upgrade -t ~ -f", (UpgradeAt "~", True, False))
+  ]
+
+upgradeParseWith :: [String] -> IO FullUpgradeOpts
+upgradeParseWith args = do
+  Upgrade a b c <- parseWith args
+  pure (a, b, c)