diff --git a/files/files.go b/files/files.go
index 9fcf422..1d85755 100644
--- a/files/files.go
+++ b/files/files.go
@@ -177,11 +177,18 @@ func ExpandContentGlobs(contents Contents, disableGlobbing bool) (files Contents
 
 func appendGlobbedFiles(all Contents, globbed map[string]string, origFile *Content) (Contents, error) {
 	for src, dst := range globbed {
+		// if the file has a FileInfo, we need to copy it but recalculate its size
+		newFileInfo := origFile.FileInfo
+		if newFileInfo != nil {
+			newFileInfoVal := *newFileInfo
+			newFileInfoVal.Size = 0
+			newFileInfo = &newFileInfoVal
+		}
 		newFile := (&Content{
 			Destination: ToNixPath(dst),
 			Source:      ToNixPath(src),
 			Type:        origFile.Type,
-			FileInfo:    origFile.FileInfo,
+			FileInfo:    newFileInfo,
 			Packager:    origFile.Packager,
 		}).WithFileInfoDefaults()
 		if dst, err := os.Readlink(src); err == nil {
diff --git a/files/files_test.go b/files/files_test.go
index 9cae87d..2166267 100644
--- a/files/files_test.go
+++ b/files/files_test.go
@@ -347,3 +347,26 @@ func TestGlobbingWhenFilesHaveBrackets(t *testing.T) {
 		}
 	}
 }
+
+func TestGlobbingFilesWithDifferentSizesWithFileInfo(t *testing.T) {
+	result, err := files.ExpandContentGlobs(files.Contents{
+		{
+			Source:      "./testdata/globtest/different-sizes/**/*",
+			Destination: ".",
+			FileInfo: &files.ContentFileInfo{
+				Mode: 0o777,
+			},
+		},
+	}, false)
+	if err != nil {
+		t.Fatalf("expand content globs: %v", err)
+	}
+
+	if len(result) != 2 {
+		t.Fatalf("unexpected result length: %d, expected 2", len(result))
+	}
+
+	if result[0].FileInfo.Size == result[1].FileInfo.Size {
+		t.Fatal("test FileInfos have the same size, expected different")
+	}
+}
diff --git a/files/testdata/globtest/different-sizes/a/a.txt b/files/testdata/globtest/different-sizes/a/a.txt
new file mode 100644
index 0000000..257cc56
--- /dev/null
+++ b/files/testdata/globtest/different-sizes/a/a.txt
@@ -0,0 +1 @@
+foo
diff --git a/files/testdata/globtest/different-sizes/b/b.txt b/files/testdata/globtest/different-sizes/b/b.txt
new file mode 100644
index 0000000..15564c6
--- /dev/null
+++ b/files/testdata/globtest/different-sizes/b/b.txt
@@ -0,0 +1 @@
+barbaz