diff --git a/cmd/stacker/grab.go b/cmd/stacker/grab.go
index 7524d6e0..bb3bb241 100644
--- a/cmd/stacker/grab.go
+++ b/cmd/stacker/grab.go
@@ -43,5 +43,5 @@ func doGrab(ctx *cli.Context) error {
 		return err
 	}
 
-	return stacker.Grab(config, s, name, parts[1], cwd, nil, -1, -1)
+	return stacker.Grab(config, s, name, parts[1], cwd, "", nil, -1, -1)
 }
diff --git a/pkg/overlay/overlay-dirs.go b/pkg/overlay/overlay-dirs.go
index 645fad86..249642f5 100644
--- a/pkg/overlay/overlay-dirs.go
+++ b/pkg/overlay/overlay-dirs.go
@@ -108,6 +108,8 @@ func validateOverlayDirs(name string, overlayDirs []types.OverlayDir, rootfs str
 		break
 	}
 
+	log.Debugf("overlayDirs: %+v", overlayDirs)
+
 	for ovlindex, ovldir := range overlayDirs {
 		if ovldir.Dest == "" {
 			continue
@@ -124,6 +126,15 @@ func validateOverlayDirs(name string, overlayDirs []types.OverlayDir, rootfs str
 				return errors.Wrapf(err, "unable to stat %s", contents)
 			}
 
+			contents, err = filepath.EvalSymlinks(contents)
+			if err != nil {
+				if errors.Is(err, os.ErrNotExist) {
+					continue
+				}
+
+				return errors.Wrapf(err, "unable to eval symlink %s", contents)
+			}
+
 			dest := path.Join(contents, ovldir.Dest)
 			realdest, err := filepath.EvalSymlinks(dest)
 			if err != nil {
@@ -135,6 +146,10 @@ func validateOverlayDirs(name string, overlayDirs []types.OverlayDir, rootfs str
 			}
 
 			overlayDirs[ovlindex].Dest = strings.TrimPrefix(realdest, contents)
+			if overlayDirs[ovlindex].Dest == "" {
+				overlayDirs[ovlindex].Dest = ovldir.Dest
+			}
+
 			if ovldir.Dest != overlayDirs[ovlindex].Dest {
 				log.Infof("overlay dest %s is a symlink, patching to %s", ovldir.Dest, overlayDirs[ovlindex].Dest)
 				break
diff --git a/pkg/stacker/grab.go b/pkg/stacker/grab.go
index 33974cf1..fdb58c92 100644
--- a/pkg/stacker/grab.go
+++ b/pkg/stacker/grab.go
@@ -11,7 +11,7 @@ import (
 )
 
 func Grab(sc types.StackerConfig, storage types.Storage, name string, source string, targetDir string,
-	mode *fs.FileMode, uid, gid int,
+	idest string, mode *fs.FileMode, uid, gid int,
 ) error {
 	c, err := container.New(sc, name)
 	if err != nil {
@@ -31,7 +31,12 @@ func Grab(sc types.StackerConfig, storage types.Storage, name string, source str
 	}
 
 	bcmd := []string{insideStaticStacker, "internal-go"}
-	err = c.Execute(append(bcmd, "cp", source, "/stacker/"+path.Base(source)), nil)
+
+	if idest == "" || source[len(source)-1:] != "/" {
+		err = c.Execute(append(bcmd, "cp", source, "/stacker/"+path.Base(source)), nil)
+	} else {
+		err = c.Execute(append(bcmd, "cp", source, "/stacker/"), nil)
+	}
 	if err != nil {
 		return err
 	}
diff --git a/pkg/stacker/import.go b/pkg/stacker/import.go
index f4d4f4a6..377b64ff 100644
--- a/pkg/stacker/import.go
+++ b/pkg/stacker/import.go
@@ -124,7 +124,17 @@ func importFile(imp string, cacheDir string, hash string, idest string, mode *fs
 		return dest, nil
 	}
 
-	dest := path.Join(cacheDir, path.Base(imp))
+	var dest string
+	if imp[len(imp)-1:] != "/" {
+		if idest != "" && path.Base(imp) != path.Base(idest) {
+			dest = path.Join(cacheDir, path.Base(idest))
+		} else {
+			dest = path.Join(cacheDir, path.Base(imp))
+		}
+	} else {
+		dest = cacheDir
+	}
+
 	if err := os.MkdirAll(dest, 0755); err != nil {
 		return "", errors.Wrapf(err, "failed making cache dir")
 	}
@@ -156,7 +166,20 @@ func importFile(imp string, cacheDir string, hash string, idest string, mode *fs
 			fallthrough
 		case mtree.Extra:
 			srcpath := path.Join(imp, d.Path())
-			destpath := path.Join(cacheDir, path.Base(imp), d.Path())
+			var destpath string
+			if imp[len(imp)-1:] != "/" {
+				if idest != "" && path.Base(imp) != path.Base(idest) {
+					if idest[len(idest)-1:] != "/" {
+						destpath = path.Join(cacheDir, path.Base(idest), d.Path())
+					} else {
+						destpath = path.Join(cacheDir, path.Base(imp), d.Path())
+					}
+				} else {
+					destpath = path.Join(cacheDir, path.Base(imp), d.Path())
+				}
+			} else {
+				destpath = path.Join(cacheDir, d.Path())
+			}
 
 			if d.New().IsDir() {
 				fi, err := os.Lstat(destpath)
@@ -260,7 +283,7 @@ func acquireUrl(c types.StackerConfig, storage types.Storage, i string, cache st
 			return "", err
 		}
 		defer cleanup()
-		err = Grab(c, storage, snap, url.Path, cache, mode, uid, gid)
+		err = Grab(c, storage, snap, url.Path, cache, idest, mode, uid, gid)
 		if err != nil {
 			return "", err
 		}
@@ -349,7 +372,7 @@ func Import(c types.StackerConfig, storage types.Storage, name string, imports t
 
 			dest := i.Dest
 
-			if i.Dest[len(i.Dest)-1:] != "/" {
+			if i.Dest[len(i.Dest)-1:] != "/" && i.Path[len(i.Path)-1:] != "/" {
 				dest = path.Dir(i.Dest)
 			}
 
diff --git a/pkg/types/layer.go b/pkg/types/layer.go
index 232303bd..2390384f 100644
--- a/pkg/types/layer.go
+++ b/pkg/types/layer.go
@@ -389,6 +389,9 @@ func (l Layer) absolutify(referenceDirectory string) (Layer, error) {
 		if err != nil {
 			return ret, err
 		}
+		if rawImport.Path[len(rawImport.Path)-1:] == "/" {
+			absImportPath += "/"
+		}
 		absImport := Import{Hash: rawImport.Hash, Path: absImportPath, Dest: rawImport.Dest, Mode: rawImport.Mode, Uid: rawImport.Uid, Gid: rawImport.Gid}
 		ret.Imports = append(ret.Imports, absImport)
 	}
diff --git a/test/import.bats b/test/import.bats
index 4623ae60..436f4f1a 100644
--- a/test/import.bats
+++ b/test/import.bats
@@ -390,6 +390,130 @@ eigth:
     [ -f /dir/file2 ]
     [ -f /dir/files/file3 ]
 EOF
+    stacker build
+}
+
+@test "import with dir contents" {
+  mkdir folder1
+  touch folder1/file1
+  mkdir folder1/subfolder2
+  touch folder1/subfolder2/subfile1
+  cat > stacker.yaml <<EOF
+first:
+  from:
+    type: oci
+    url: $CENTOS_OCI
+  import:
+  - path: folder1/
+    dest: /folder1/
+  run: |
+    [ -f /folder1/file1 ]
+
+second:
+  from:
+    type: built
+    tag: first
+  run: |
+    mkdir -p /folder1
+    touch /folder1/file1
+    touch /folder1/file2
+
+third:
+  from:
+    type: oci
+    url: $CENTOS_OCI
+  import:
+    - path: stacker://second/folder1/
+      dest: /folder1/
+  run: |
+    [ -f /folder1/file1 ]
+    [ -f /folder1/file2 ]
 
+fourth:
+  from:
+    type: oci
+    url: $CENTOS_OCI
+  import:
+  - path: folder1/
+    dest: /
+  run: |
+    ls -l /
+    [ -f /file1 ]
+    mkdir -p /folder4/subfolder5
+    touch /folder4/subfolder5/subfile6
+
+fifth:
+  from:
+    type: oci
+    url: $CENTOS_OCI
+  import:
+  - path: folder1/subfolder2/
+    dest: /folder3/
+  - path: folder1/subfolder2
+    dest: /folder4
+  - path: stacker://fourth/folder4/subfolder5/
+    dest: /folder6/
+  - path: stacker://fourth/folder4/
+    dest: /folder7/
+  run: |
+    ls -l /folder*
+    [ -f /folder3/subfile1 ]
+    [ ! -e /folder3/subfolder2 ]
+    [ -f /folder4/subfile1 ]
+    [ -f /folder6/subfile6 ]
+    [ ! -e /folder6/subfolder5 ]
+    [ -f /folder7/subfolder5/subfile6 ]
+EOF
     stacker build
 }
+
+@test "dir path behavior" {
+  mkdir -p folder1
+  touch folder1/file1
+  mkdir -p folder1/subfolder2
+  touch folder1/subfolder2/subfile1
+  cat > stacker.yaml <<EOF
+src_folder_dest_non_existent_folder_case1:
+  from:
+    type: docker
+    url: docker://ubuntu:latest
+  import:
+  - path: folder1
+    dest: /folder2
+  run: |
+    [ -f /folder2/file1 ]
+
+src_folder_dest_non_existent_folder_case2:
+  from:
+    type: docker
+    url: docker://ubuntu:latest
+  import:
+  - path: folder1/
+    dest: /folder2
+  run: |
+    [ -f /folder2/file1 ]
+
+src_folder_dest_non_existent_folder_case3:
+  from:
+    type: docker
+    url: docker://ubuntu:latest
+  import:
+  - path: folder1
+    dest: /folder2/
+  run: |
+    ls -al /
+    ls -al /folder2
+    [ -f /folder2/folder1/file1 ]
+
+src_folder_dest_non_existent_folder_case4:
+  from:
+    type: docker
+    url: docker://ubuntu:latest
+  import:
+  - path: folder1/
+    dest: /folder2/
+  run: |
+    [ -f /folder2/file1 ]
+EOF
+  stacker build
+}