diff --git a/app/App.hs b/app/App.hs
index e63a739..99d0c09 100644
--- a/app/App.hs
+++ b/app/App.hs
@@ -28,6 +28,7 @@ type AppConfig = MonadReader Options
 data AppError
     = TagError TagSearchOutcome
     | InvalidConfigError [ParseConfigError]
+    | CacheError FingerprintOutcome
 
 newtype App a = App {
     runApp :: ReaderT Options (ExceptT AppError IO) a
@@ -68,6 +69,7 @@ termsWithAlternatesFromConfig = do
 renderError :: AppError -> IO ()
 renderError (TagError e) = V.missingTagsFileError e
 renderError (InvalidConfigError e) = V.invalidConfigError e
+renderError (CacheError e) = V.fingerprintError e
 
 retrieveGitContext :: TermMatchSet -> App TermMatchSet
 retrieveGitContext tms = do
@@ -97,10 +99,14 @@ calculateTagInput = do
 
 withCache :: IO SearchResults -> App SearchResults
 withCache f =
-    liftIO . operateCache =<< runWithCache
+    operateCache =<< runWithCache
   where
-    operateCache b = if b then withCache' f else f
-    withCache' = fmap SearchResults . cached "term-matches" . fmap fromResults
+    operateCache b = if b then withCache' f else liftIO f
+    withCache' :: IO SearchResults -> App SearchResults
+    withCache' r =
+        either (throwError . CacheError) (return . SearchResults) =<<
+            liftIO (cached "term-matches" $ fmap fromResults r)
+
 
 optionFilters :: AppConfig m => TermMatchSet -> m TermMatchSet
 optionFilters tms = foldl (>>=) (pure tms) matchSetFilters
diff --git a/src/Unused/CLI/Views.hs b/src/Unused/CLI/Views.hs
index 256a5dc..b7a5545 100644
--- a/src/Unused/CLI/Views.hs
+++ b/src/Unused/CLI/Views.hs
@@ -7,4 +7,5 @@ import Unused.CLI.Views.AnalysisHeader as X
 import Unused.CLI.Views.GitSHAsHeader as X
 import Unused.CLI.Views.MissingTagsFileError as X
 import Unused.CLI.Views.InvalidConfigError as X
+import Unused.CLI.Views.FingerprintError as X
 import Unused.CLI.Views.SearchResult as X
diff --git a/src/Unused/CLI/Views/FingerprintError.hs b/src/Unused/CLI/Views/FingerprintError.hs
new file mode 100644
index 0000000..c7edaf6
--- /dev/null
+++ b/src/Unused/CLI/Views/FingerprintError.hs
@@ -0,0 +1,19 @@
+module Unused.CLI.Views.FingerprintError
+    ( fingerprintError
+    ) where
+
+import Data.List (intercalate)
+import Unused.Cache.DirectoryFingerprint
+import Unused.CLI.Views.Error
+
+fingerprintError :: FingerprintOutcome -> IO ()
+fingerprintError e = do
+    errorHeader "There was a problem generating a cache fingerprint:"
+
+    printOutcomeMessage e
+
+printOutcomeMessage :: FingerprintOutcome -> IO ()
+printOutcomeMessage (MD5ExecutableNotFound execs) =
+    putStrLn $
+        "Unable to find any of the following executables \
+        \in your PATH: " ++ intercalate ", " execs
diff --git a/src/Unused/Cache.hs b/src/Unused/Cache.hs
index 90de308..772f6da 100644
--- a/src/Unused/Cache.hs
+++ b/src/Unused/Cache.hs
@@ -1,5 +1,6 @@
 module Unused.Cache
-    ( cached
+    ( FingerprintOutcome(..)
+    , cached
     ) where
 
 import Control.Monad.IO.Class (liftIO)
@@ -8,16 +9,16 @@ import System.Directory
 import Data.Csv (FromRecord, ToRecord, HasHeader(..), encode, decode)
 import Data.Vector (toList)
 import qualified Data.ByteString.Lazy as BS
-import Unused.Cache.DirectoryFingerprint (sha)
+import Unused.Cache.DirectoryFingerprint
 
 newtype CacheFileName = CacheFileName String
 type Cache = ReaderT CacheFileName IO
 
-cached :: (FromRecord a, ToRecord a) => String -> IO [a] -> IO [a]
-cached context f =
-    runReaderT fromCache =<< cacheFileName context
+cached :: (FromRecord a, ToRecord a) => String -> IO [a] -> IO (Either FingerprintOutcome [a])
+cached cachePrefix f =
+    mapM fromCache =<< cacheFileName cachePrefix
   where
-    fromCache = maybe (writeCache =<< liftIO f) return =<< readCache
+    fromCache = runReaderT $ maybe (writeCache =<< liftIO f) return =<< readCache
 
 writeCache :: ToRecord a => [a] -> Cache [a]
 writeCache [] = return []
@@ -38,11 +39,12 @@ readCache = do
   where
     processCsv = either (const Nothing) (Just . toList)
 
-cacheFileName :: String -> IO CacheFileName
+cacheFileName :: String -> IO (Either FingerprintOutcome CacheFileName)
 cacheFileName context = do
     putStrLn "\n\nCalculating cache fingerprint... "
-    currentSha <- sha
-    return $ CacheFileName $ cacheDirectory ++ "/" ++ context ++ "-" ++ currentSha ++ ".csv"
+    fmap toFileName <$> sha
+  where
+    toFileName s = CacheFileName $ cacheDirectory ++ "/" ++ context ++ "-" ++ s ++ ".csv"
 
 cacheDirectory :: String
 cacheDirectory = "tmp/unused"
diff --git a/src/Unused/Cache/DirectoryFingerprint.hs b/src/Unused/Cache/DirectoryFingerprint.hs
index 62aa6ba..908c065 100644
--- a/src/Unused/Cache/DirectoryFingerprint.hs
+++ b/src/Unused/Cache/DirectoryFingerprint.hs
@@ -1,31 +1,53 @@
 module Unused.Cache.DirectoryFingerprint
-    ( sha
+    ( FingerprintOutcome(..)
+    , sha
     ) where
 
 import System.Process
+import Control.Monad.IO.Class (liftIO)
+import Control.Monad.Trans.Reader
+import qualified System.Directory as D
+import qualified Data.Char as C
 import Data.Maybe (fromMaybe)
 import Unused.Cache.FindArgsFromIgnoredPaths
-import Unused.Util (readIfFileExists)
+import Unused.Util (safeHead, readIfFileExists)
 
-sha :: IO String
-sha =
-    getSha <$> (fileList >>= sortInput >>= md5Result)
+type MD5Config = ReaderT String IO
+
+data FingerprintOutcome
+    = MD5ExecutableNotFound [String]
+
+sha :: IO (Either FingerprintOutcome String)
+sha = do
+    md5Executable' <- md5Executable
+    case md5Executable' of
+        Just exec ->
+            Right . getSha <$> runReaderT (fileList >>= sortInput >>= md5Result) exec
+        Nothing -> return $ Left $ MD5ExecutableNotFound supportedMD5Executables
   where
-    getSha = head' . lines
-    head' (x:_) = x
-    head' _ = ""
+    getSha = takeWhile C.isAlphaNum . fromMaybe "" . safeHead . lines
 
-fileList :: IO String
+fileList :: MD5Config String
 fileList = do
-    filterNamePathArgs <- findArgs <$> ignoredPaths
-    let args = [".", "-type", "f", "-not", "-path", "*/.git/*"] ++ filterNamePathArgs ++ ["-exec", "md5", "{}", "+"]
-    readProcess "find" args ""
+    filterNamePathArgs <- liftIO $ findArgs <$> ignoredPaths
+    md5exec <- ask
+    let args = [".", "-type", "f", "-not", "-path", "*/.git/*"] ++ filterNamePathArgs ++ ["-exec", md5exec, "{}", "+"]
+    liftIO $ readProcess "find" args ""
 
-sortInput :: String -> IO String
-sortInput = readProcess "sort" ["-k", "2"]
+sortInput :: String -> MD5Config String
+sortInput = liftIO . readProcess "sort" ["-k", "2"]
 
-md5Result :: String -> IO String
-md5Result = readProcess "md5" []
+md5Result :: String -> MD5Config String
+md5Result r = do
+    md5exec <- ask
+    liftIO $ readProcess md5exec [] r
 
 ignoredPaths :: IO [String]
 ignoredPaths = fromMaybe [] <$> (fmap lines <$> readIfFileExists ".gitignore")
+
+md5Executable :: IO (Maybe String)
+md5Executable =
+    safeHead . concat <$> mapM D.findExecutables supportedMD5Executables
+
+supportedMD5Executables :: [String]
+supportedMD5Executables = ["md5", "md5sum"]
diff --git a/src/Unused/Util.hs b/src/Unused/Util.hs
index efb48ff..4be70ce 100644
--- a/src/Unused/Util.hs
+++ b/src/Unused/Util.hs
@@ -1,6 +1,7 @@
 module Unused.Util
     ( groupBy
     , stringToInt
+    , safeHead
     , readIfFileExists
     ) where
 
@@ -15,6 +16,10 @@ groupBy f = map (f . head &&& id)
                    . L.groupBy ((==) `on` f)
                    . L.sortBy (compare `on` f)
 
+safeHead :: [a] -> Maybe a
+safeHead (x:_) = Just x
+safeHead _ = Nothing
+
 stringToInt :: String -> Maybe Int
 stringToInt xs
     | all isDigit xs = Just $ loop 0 xs
diff --git a/unused.cabal b/unused.cabal
index 8763d97..9c7cdac 100644
--- a/unused.cabal
+++ b/unused.cabal
@@ -48,6 +48,7 @@ library
                      , Unused.CLI.Views.GitSHAsHeader
                      , Unused.CLI.Views.MissingTagsFileError
                      , Unused.CLI.Views.InvalidConfigError
+                     , Unused.CLI.Views.FingerprintError
                      , Unused.CLI.Views.SearchResult
                      , Unused.CLI.Views.SearchResult.ColumnFormatter
                      , Unused.CLI.Views.SearchResult.Internal