diff --git a/app/ghcup/BrickMain.hs b/app/ghcup/BrickMain.hs
index 1c3b323..4edad3a 100644
--- a/app/ghcup/BrickMain.hs
+++ b/app/ghcup/BrickMain.hs
@@ -17,6 +17,7 @@ import           GHCup.Prelude ( decUTF8Safe )
 import           GHCup.Prelude.File
 import           GHCup.Prelude.Logger
 import           GHCup.Prelude.Process
+import           GHCup.Prompts
 
 import           Brick
 import           Brick.Widgets.Border
@@ -52,6 +53,8 @@ import           Text.PrettyPrint.HughesPJClass ( prettyShow )
 import           URI.ByteString
 
 import qualified Data.Text                     as T
+import qualified Data.Text.Lazy.Builder        as B
+import qualified Data.Text.Lazy                as L
 import qualified Graphics.Vty                  as Vty
 import qualified Data.Vector                   as V
 import System.Environment (getExecutablePath)
@@ -98,7 +101,7 @@ keyHandlers KeyBindings {..} =
   [ (bQuit, const "Quit"     , halt)
   , (bInstall, const "Install"  , withIOAction install')
   , (bUninstall, const "Uninstall", withIOAction del')
-  , (bSet, const "Set"      , withIOAction ((liftIO .) . set'))
+  , (bSet, const "Set"      , withIOAction set')
   , (bChangelog, const "ChangeLog", withIOAction changelog')
   , ( bShowAllVersions
     , \BrickSettings {..} ->
@@ -486,9 +489,12 @@ install' _ (_, ListResult {..}) = do
             <> "Also check the logs in ~/.ghcup/logs"
 
 
-set' :: BrickState -> (Int, ListResult) -> IO (Either String ())
-set' _ (_, ListResult {..}) = do
-  settings <- readIORef settings'
+set' :: (MonadReader AppState m, MonadIO m, MonadThrow m, MonadFail m, MonadMask m, MonadUnliftIO m)
+     => BrickState
+     -> (Int, ListResult)
+     -> m (Either String ())
+set' bs input@(_, ListResult {..}) = do
+  settings <- liftIO $ readIORef settings'
 
   let run =
         flip runReaderT settings
@@ -504,7 +510,28 @@ set' _ (_, ListResult {..}) = do
     )
     >>= \case
           VRight _ -> pure $ Right ()
-          VLeft  e -> pure $ Left (prettyShow e)
+          VLeft  e -> case e of
+            (V (NotInstalled tool _)) -> do
+              promptAnswer <- getUserPromptResponse userPrompt
+              case promptAnswer of
+                PromptYes -> do
+                  res <- install' bs input
+                  case res of
+                    (Left err) -> pure $ Left err
+                    (Right _) -> do
+                      logInfo "Setting now..."
+                      set' bs input
+
+                PromptNo -> pure $ Left (prettyShow e)
+              where
+                userPrompt = L.toStrict . B.toLazyText . B.fromString $
+                  "This Version of "
+                  <> show tool
+                  <> " you are trying to set is not installed.\n"
+                  <> "Would you like to install it first? [Y/N]: "
+
+            _ -> pure $ Left (prettyShow e)
+
 
 
 del' :: (MonadReader AppState m, MonadIO m, MonadFail m, MonadMask m, MonadUnliftIO m)
diff --git a/ghcup.cabal b/ghcup.cabal
index fb2293d..1b27e95 100644
--- a/ghcup.cabal
+++ b/ghcup.cabal
@@ -69,6 +69,7 @@ library
     GHCup.Prelude.Process
     GHCup.Prelude.String.QQ
     GHCup.Prelude.Version.QQ
+    GHCup.Prompts
     GHCup.Requirements
     GHCup.Stack
     GHCup.Types
diff --git a/lib/GHCup/Prompts.hs b/lib/GHCup/Prompts.hs
new file mode 100644
index 0000000..2b60845
--- /dev/null
+++ b/lib/GHCup/Prompts.hs
@@ -0,0 +1,28 @@
+{-# LANGUAGE OverloadedStrings #-}
+{-# LANGUAGE FlexibleContexts #-}
+
+module GHCup.Prompts
+  ( PromptQuestion,
+    PromptResponse (..),
+    getUserPromptResponse,
+  )
+where
+
+import Control.Monad.Reader
+import qualified Data.Text.IO as TIO
+import GHCup.Prelude.Logger
+import GHCup.Types.Optics
+import GHCup.Types (PromptQuestion, PromptResponse(..))
+
+getUserPromptResponse :: ( HasLog env
+                         , MonadReader env m
+                         , MonadIO m)
+                      => PromptQuestion
+                      -> m PromptResponse
+
+getUserPromptResponse prompt = do
+  logInfo prompt
+  resp <- liftIO TIO.getLine
+  if resp `elem` ["YES", "yes", "y", "Y"]
+    then pure PromptYes
+    else pure PromptNo
diff --git a/lib/GHCup/Types.hs b/lib/GHCup/Types.hs
index 75f4083..3bd66d0 100644
--- a/lib/GHCup/Types.hs
+++ b/lib/GHCup/Types.hs
@@ -657,3 +657,7 @@ isSafeDir (IsolateDirResolved _) = False
 isSafeDir (GHCupDir _)           = True
 isSafeDir (GHCupBinDir _)        = False
 
+type PromptQuestion = Text
+
+data PromptResponse = PromptYes | PromptNo
+  deriving (Show, Eq)