diff --git a/Cabal/ChangeLog.md b/Cabal/ChangeLog.md
index fc8e3916fb4..3987a11a762 100644
--- a/Cabal/ChangeLog.md
+++ b/Cabal/ChangeLog.md
@@ -61,6 +61,8 @@
     path components on Windows and warn about other unsafe characters
     in the path to the source directory on all platforms
     ([#5386](https://github.com/haskell/cabal/issues/5386)).
+  * `cabal check` now warns about globs that refer to missing
+    directories.
 
 ----
 
diff --git a/Cabal/Distribution/PackageDescription/Check.hs b/Cabal/Distribution/PackageDescription/Check.hs
index 86027baa39b..2000d33bfe5 100644
--- a/Cabal/Distribution/PackageDescription/Check.hs
+++ b/Cabal/Distribution/PackageDescription/Check.hs
@@ -1843,11 +1843,11 @@ checkDevelopmentOnlyFlags pkg =
 checkPackageFiles :: PackageDescription -> FilePath -> NoCallStackIO [PackageCheck]
 checkPackageFiles pkg root = do
   contentChecks <- checkPackageContent checkFilesIO pkg
-  missingFileChecks <- checkPackageMissingFiles pkg root
+  preDistributionChecks <- checkPackageFilesPreDistribution pkg root
   -- Sort because different platforms will provide files from
   -- `getDirectoryContents` in different orders, and we'd like to be
   -- stable for test output.
-  return (sort contentChecks ++ sort missingFileChecks)
+  return (sort contentChecks ++ sort preDistributionChecks)
   where
     checkFilesIO = CheckPackageContentOps {
       doesFileExist        = System.doesFileExist                  . relative,
@@ -2143,40 +2143,31 @@ checkTarPath path
       ++ "Files with an empty name cannot be stored in a tar archive or in "
       ++ "standard file systems."
 
--- ------------------------------------------------------------
--- * Checks for missing content
--- ------------------------------------------------------------
+-- --------------------------------------------------------------
+-- * Checks for missing content and other pre-distribution checks
+-- --------------------------------------------------------------
 
--- | Similar to 'checkPackageContent', 'checkPackageMissingFiles' inspects
--- the files included in the package, but is primarily looking for files in
--- the working tree that may have been missed.
+-- | Similar to 'checkPackageContent', 'checkPackageFilesPreDistribution'
+-- inspects the files included in the package, but is primarily looking for
+-- files in the working tree that may have been missed or other similar
+-- problems that can only be detected pre-distribution.
 --
 -- Because Hackage necessarily checks the uploaded tarball, it is too late to
 -- check these on the server; these checks only make sense in the development
 -- and package-creation environment. Hence we can use IO, rather than needing
 -- to pass a 'CheckPackageContentOps' dictionary around.
-checkPackageMissingFiles :: PackageDescription -> FilePath -> NoCallStackIO [PackageCheck]
-checkPackageMissingFiles = checkGlobMultiDot
-
--- | Before Cabal 2.4, the extensions of globs had to match the file
--- exactly. This has been relaxed in 2.4 to allow matching only the
--- suffix. This warning detects when pre-2.4 package descriptions are
--- omitting files purely because of the stricter check.
-checkGlobMultiDot :: PackageDescription
-                  -> FilePath
-                  -> NoCallStackIO [PackageCheck]
-checkGlobMultiDot pkg root =
+checkPackageFilesPreDistribution :: PackageDescription -> FilePath -> NoCallStackIO [PackageCheck]
+checkPackageFilesPreDistribution = checkGlobFiles
+
+-- | Discover problems with the package's wildcards.
+checkGlobFiles :: PackageDescription
+               -> FilePath
+               -> NoCallStackIO [PackageCheck]
+checkGlobFiles pkg root =
   fmap concat $ for allGlobs $ \(field, dir, glob) -> do
     --TODO: baked-in verbosity
     results <- matchDirFileGlob' normal (specVersion pkg) (root </> dir) glob
-    return
-      [ PackageDistSuspiciousWarn $
-             "In '" ++ field ++ "': the pattern '" ++ glob ++ "' does not"
-          ++ " match the file '" ++ file ++ "' because the extensions do not"
-          ++ " exactly match (e.g., foo.en.html does not exactly match *.html)."
-          ++ " To enable looser suffix-only matching, set 'cabal-version: 2.4' or higher."
-      | GlobWarnMultiDot file <- results
-      ]
+    return $ results >>= getWarning field glob
   where
     adjustedDataDir = if null (dataDir pkg) then "." else dataDir pkg
     allGlobs = concat
@@ -2184,6 +2175,26 @@ checkGlobMultiDot pkg root =
       , (,,) "extra-doc-files" "." <$> extraDocFiles pkg
       , (,,) "data-files" adjustedDataDir <$> dataFiles pkg
       ]
+    getWarning :: String -> FilePath -> GlobResult FilePath -> [PackageCheck]
+    getWarning _ _ (GlobMatch _) =
+      []
+    -- Before Cabal 2.4, the extensions of globs had to match the file
+    -- exactly. This has been relaxed in 2.4 to allow matching only the
+    -- suffix. This warning detects when pre-2.4 package descriptions are
+    -- omitting files purely because of the stricter check.
+    getWarning field glob (GlobWarnMultiDot file) =
+      [ PackageDistSuspiciousWarn $
+             "In '" ++ field ++ "': the pattern '" ++ glob ++ "' does not"
+          ++ " match the file '" ++ file ++ "' because the extensions do not"
+          ++ " exactly match (e.g., foo.en.html does not exactly match *.html)."
+          ++ " To enable looser suffix-only matching, set 'cabal-version: 2.4' or higher."
+      ]
+    getWarning field glob (GlobMissingDirectory dir) =
+      [ PackageDistInexcusable $
+             "In '" ++ field ++ "': the pattern '" ++ glob ++ "' attempts to"
+          ++ " match files in the directory '" ++ dir ++ "', but there is no"
+          ++ " directory by that name."
+      ]
 
 -- ------------------------------------------------------------
 -- * Utils
diff --git a/Cabal/Distribution/Simple/Glob.hs b/Cabal/Distribution/Simple/Glob.hs
index 629f45cf60a..0b488ee776e 100644
--- a/Cabal/Distribution/Simple/Glob.hs
+++ b/Cabal/Distribution/Simple/Glob.hs
@@ -17,7 +17,6 @@
 module Distribution.Simple.Glob (
         GlobSyntaxError(..),
         GlobResult(..),
-        globMatches,
         matchDirFileGlob,
         matchDirFileGlob',
         fileGlobMatches,
@@ -35,7 +34,7 @@ import Distribution.Simple.Utils
 import Distribution.Verbosity
 import Distribution.Version
 
-import System.Directory (getDirectoryContents, doesFileExist)
+import System.Directory (getDirectoryContents, doesDirectoryExist, doesFileExist)
 import System.FilePath (joinPath, splitExtensions, splitDirectories, takeFileName, (</>))
 
 -- Note throughout that we use splitDirectories, not splitPath. On
@@ -52,9 +51,17 @@ data GlobResult a
     --   not precisely match the glob's extensions, but rather the
     --   glob was a proper suffix of the file's extensions; i.e., if
     --   not for the low cabal-version, it would have matched.
+  | GlobMissingDirectory FilePath
+    -- ^ The glob couldn't match because the directory named doesn't
+    --   exist. The directory will be as it appears in the glob (i.e.,
+    --   relative to the directory passed to 'matchDirFileGlob', and,
+    --   for 'data-files', relative to 'data-dir').
   deriving (Show, Eq, Ord, Functor)
 
 -- | Extract the matches from a list of 'GlobResult's.
+--
+-- Note: throws away the 'GlobMissingDirectory' results; chances are
+-- that you want to check for these and error out if any are present.
 globMatches :: [GlobResult a] -> [a]
 globMatches input = [ a | GlobMatch a <- input ]
 
@@ -193,11 +200,20 @@ parseFileGlob version filepath = case reverse (splitDirectories filepath) of
       | otherwise = MultiDotDisabled
 
 -- | Like 'matchDirFileGlob'', but will 'die'' when the glob matches
--- no files.
-matchDirFileGlob :: Verbosity -> Version -> FilePath -> FilePath -> IO [GlobResult FilePath]
+-- no files, or if the glob refers to a missing directory.
+matchDirFileGlob :: Verbosity -> Version -> FilePath -> FilePath -> IO [FilePath]
 matchDirFileGlob verbosity version dir filepath = do
-  matches <- matchDirFileGlob' verbosity version dir filepath
-  when (null $ globMatches matches) $ die' verbosity $
+  results <- matchDirFileGlob' verbosity version dir filepath
+  let missingDirectories =
+        [ missingDir | GlobMissingDirectory missingDir <- results ]
+      matches = globMatches results
+  -- Check for missing directories first, since we'll obviously have
+  -- no matches in that case.
+  for_ missingDirectories $ \ missingDir ->
+    die' verbosity $
+         "filepath wildcard '" ++ filepath ++ "' refers to the directory"
+      ++ " '" ++ missingDir ++ "', which does not exist or is not a directory."
+  when (null matches) $ die' verbosity $
        "filepath wildcard '" ++ filepath
     ++ "' does not match any files."
   return matches
@@ -231,15 +247,20 @@ matchDirFileGlob' verbosity version rawDir filepath = case parseFileGlob version
     case final of
       FinalMatch recursive multidot exts -> do
         let prefix = dir </> joinedPrefix
-        candidates <- case recursive of
-          Recursive -> getDirectoryContentsRecursive prefix
-          NonRecursive -> filterM (doesFileExist . (prefix </>)) =<< getDirectoryContents prefix
-        let checkName candidate = do
-              let (candidateBase, candidateExts) = splitExtensions $ takeFileName candidate
-              guard (not (null candidateBase))
-              match <- checkExt multidot exts candidateExts
-              return (joinedPrefix </> candidate <$ match)
-        return $ mapMaybe checkName candidates
+        directoryExists <- doesDirectoryExist prefix
+        if directoryExists
+          then do
+            candidates <- case recursive of
+              Recursive -> getDirectoryContentsRecursive prefix
+              NonRecursive -> filterM (doesFileExist . (prefix </>)) =<< getDirectoryContents prefix
+            let checkName candidate = do
+                  let (candidateBase, candidateExts) = splitExtensions $ takeFileName candidate
+                  guard (not (null candidateBase))
+                  match <- checkExt multidot exts candidateExts
+                  return (joinedPrefix </> candidate <$ match)
+            return $ mapMaybe checkName candidates
+          else
+            return [ GlobMissingDirectory joinedPrefix ]
       FinalLit fn -> do
         exists <- doesFileExist (dir </> joinedPrefix </> fn)
         return [ GlobMatch (joinedPrefix </> fn) | exists ]
diff --git a/Cabal/Distribution/Simple/Haddock.hs b/Cabal/Distribution/Simple/Haddock.hs
index 7f2495ecf16..13e79755a8c 100644
--- a/Cabal/Distribution/Simple/Haddock.hs
+++ b/Cabal/Distribution/Simple/Haddock.hs
@@ -306,7 +306,7 @@ haddock pkg_descr lbi suffixes flags' = do
         CBench _ -> (when (flag haddockBenchmarks)  $ smsg >> doExe component) >> return index
 
     for_ (extraDocFiles pkg_descr) $ \ fpath -> do
-      files <- fmap globMatches $ matchDirFileGlob verbosity (specVersion pkg_descr) "." fpath
+      files <- matchDirFileGlob verbosity (specVersion pkg_descr) "." fpath
       for_ files $ copyFileTo verbosity (unDir $ argOutputDir commonArgs)
 
 -- ------------------------------------------------------------------------------
diff --git a/Cabal/Distribution/Simple/Install.hs b/Cabal/Distribution/Simple/Install.hs
index 26b7d361856..83305bc0dc5 100644
--- a/Cabal/Distribution/Simple/Install.hs
+++ b/Cabal/Distribution/Simple/Install.hs
@@ -33,7 +33,7 @@ import Distribution.Package
 import Distribution.PackageDescription
 import Distribution.Simple.LocalBuildInfo
 import Distribution.Simple.BuildPaths (haddockName, haddockPref)
-import Distribution.Simple.Glob (matchDirFileGlob, globMatches)
+import Distribution.Simple.Glob (matchDirFileGlob)
 import Distribution.Simple.Utils
          ( createDirectoryIfMissingVerbose
          , installDirectoryContents, installOrdinaryFile, isInSearchPath
@@ -238,7 +238,7 @@ installDataFiles verbosity pkg_descr destDataDir =
         srcDataDir = if null srcDataDirRaw
           then "."
           else srcDataDirRaw
-    files <- globMatches <$> matchDirFileGlob verbosity (specVersion pkg_descr) srcDataDir file
+    files <- matchDirFileGlob verbosity (specVersion pkg_descr) srcDataDir file
     let dir = takeDirectory file
     createDirectoryIfMissingVerbose verbosity True (destDataDir </> dir)
     sequence_ [ installOrdinaryFile verbosity (srcDataDir  </> file')
diff --git a/Cabal/Distribution/Simple/SrcDist.hs b/Cabal/Distribution/Simple/SrcDist.hs
index 06560164b75..613d13896b3 100644
--- a/Cabal/Distribution/Simple/SrcDist.hs
+++ b/Cabal/Distribution/Simple/SrcDist.hs
@@ -148,8 +148,7 @@ listPackageSourcesMaybeExecutable :: Verbosity -> PackageDescription -> IO [File
 listPackageSourcesMaybeExecutable verbosity pkg_descr =
   -- Extra source files.
   fmap concat . for (extraSrcFiles pkg_descr) $ \fpath ->
-    fmap globMatches $
-      matchDirFileGlob verbosity (specVersion pkg_descr) "." fpath
+    matchDirFileGlob verbosity (specVersion pkg_descr) "." fpath
 
 -- | List those source files that should be copied with ordinary permissions.
 listPackageSourcesOrdinary :: Verbosity
@@ -216,13 +215,11 @@ listPackageSourcesOrdinary verbosity pkg_descr pps =
               then "."
               else srcDataDirRaw
         in fmap (fmap (srcDataDir </>)) $
-             fmap globMatches $
-               matchDirFileGlob verbosity (specVersion pkg_descr) srcDataDir filename
+             matchDirFileGlob verbosity (specVersion pkg_descr) srcDataDir filename
 
     -- Extra doc files.
   , fmap concat
     . for (extraDocFiles pkg_descr) $ \ filename ->
-      fmap globMatches $
         matchDirFileGlob verbosity (specVersion pkg_descr) "." filename
 
     -- License file(s).
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/Foo.hs b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/Foo.hs
new file mode 100644
index 00000000000..85e9b7cee73
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/Foo.hs
@@ -0,0 +1 @@
+foo = True
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/cabal.out b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/cabal.out
new file mode 100644
index 00000000000..c9cc011d477
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/cabal.out
@@ -0,0 +1,9 @@
+# cabal check
+Warning: The package will not build sanely due to these errors:
+Warning: This package description follows version 2.4 of the Cabal specification. This tool only supports up to version 2.3.0.0.
+Warning: The following errors will cause portability problems on other environments:
+Warning: In 'data-files': the pattern 'another-non-existent-directory/**/*.dat' attempts to match files in the directory 'another-non-existent-directory', but there is no directory by that name.
+Warning: In 'extra-doc-files': the pattern 'non-existent-directory/*.html' attempts to match files in the directory 'non-existent-directory', but there is no directory by that name.
+Warning: In 'extra-doc-files': the pattern 'present/present/missing/*.tex' attempts to match files in the directory 'present/present/missing', but there is no directory by that name.
+Warning: In 'extra-source-files': the pattern 'file-not-a-directory/*.js' attempts to match files in the directory 'file-not-a-directory', but there is no directory by that name.
+Warning: Hackage would reject this package.
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/cabal.test.hs b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/cabal.test.hs
new file mode 100644
index 00000000000..3e2d39fa5bc
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/cabal.test.hs
@@ -0,0 +1,3 @@
+import Test.Cabal.Prelude
+main = cabalTest $
+  fails $ cabal "check" []
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/data/hello.dat b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/data/hello.dat
new file mode 100644
index 00000000000..6d96d67d915
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/data/hello.dat
@@ -0,0 +1 @@
+hello.dat
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/file-not-a-directory b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/file-not-a-directory
new file mode 100644
index 00000000000..cd00d26af7e
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/file-not-a-directory
@@ -0,0 +1 @@
+This is not a directory.
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/pkg.cabal b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/pkg.cabal
new file mode 100644
index 00000000000..35b580e2304
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/pkg.cabal
@@ -0,0 +1,21 @@
+cabal-version: 2.4
+name: pkg
+version: 0
+extra-doc-files:
+  non-existent-directory/*.html
+  present/present/missing/*.tex
+extra-source-files:
+  file-not-a-directory/*.js
+data-dir:
+  data
+data-files:
+  another-non-existent-directory/**/*.dat
+category: example
+maintainer: none@example.com
+synopsis: synopsis
+description: description
+license: BSD-3-Clause
+
+library
+  exposed-modules: Foo
+  default-language: Haskell2010
\ No newline at end of file
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/present/present/hello b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/present/present/hello
new file mode 100644
index 00000000000..1e4f8c34022
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory/present/present/hello
@@ -0,0 +1 @@
+This file only exists so that Git will create its two parent directories.
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/Foo.hs b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/Foo.hs
new file mode 100644
index 00000000000..85e9b7cee73
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/Foo.hs
@@ -0,0 +1 @@
+foo = True
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/cabal.out b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/cabal.out
new file mode 100644
index 00000000000..e62a8a5329b
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/cabal.out
@@ -0,0 +1,6 @@
+# cabal check
+Warning: The package will not build sanely due to these errors:
+Warning: This package description follows version 2.4 of the Cabal specification. This tool only supports up to version 2.3.0.0.
+Warning: The following errors will cause portability problems on other environments:
+Warning: In 'data-files': the pattern 'non-existent-directory/**/*.dat' attempts to match files in the directory 'non-existent-directory', but there is no directory by that name.
+Warning: Hackage would reject this package.
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/cabal.test.hs b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/cabal.test.hs
new file mode 100644
index 00000000000..3e2d39fa5bc
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/cabal.test.hs
@@ -0,0 +1,3 @@
+import Test.Cabal.Prelude
+main = cabalTest $
+  fails $ cabal "check" []
diff --git a/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/pkg.cabal b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/pkg.cabal
new file mode 100644
index 00000000000..29a45267a8a
--- /dev/null
+++ b/cabal-testsuite/PackageTests/Check/MissingGlobDirectory2/pkg.cabal
@@ -0,0 +1,14 @@
+cabal-version: 2.4
+name: pkg
+version: 0
+data-files:
+  non-existent-directory/**/*.dat
+category: example
+maintainer: none@example.com
+synopsis: synopsis
+description: description
+license: BSD-3-Clause
+
+library
+  exposed-modules: Foo
+  default-language: Haskell2010
\ No newline at end of file