diff --git a/bundle/bundle.go b/bundle/bundle.go
index 977ca224..1dc98656 100644
--- a/bundle/bundle.go
+++ b/bundle/bundle.go
@@ -22,6 +22,7 @@ import (
 	"github.com/databricks/cli/libs/log"
 	"github.com/databricks/cli/libs/tags"
 	"github.com/databricks/cli/libs/terraform"
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/databricks/databricks-sdk-go"
 	sdkconfig "github.com/databricks/databricks-sdk-go/config"
 	"github.com/hashicorp/terraform-exec/tfexec"
@@ -208,7 +209,7 @@ func (b *Bundle) GitRepository() (*git.Repository, error) {
 		return nil, fmt.Errorf("unable to locate repository root: %w", err)
 	}
 
-	return git.NewRepository(rootPath)
+	return git.NewRepository(vfs.MustNew(rootPath))
 }
 
 // AuthEnv returns a map with environment variables and their values
diff --git a/bundle/config/mutator/load_git_details.go b/bundle/config/mutator/load_git_details.go
index 7ce8476f..d8b76f39 100644
--- a/bundle/config/mutator/load_git_details.go
+++ b/bundle/config/mutator/load_git_details.go
@@ -8,6 +8,7 @@ import (
 	"github.com/databricks/cli/libs/diag"
 	"github.com/databricks/cli/libs/git"
 	"github.com/databricks/cli/libs/log"
+	"github.com/databricks/cli/libs/vfs"
 )
 
 type loadGitDetails struct{}
@@ -22,7 +23,7 @@ func (m *loadGitDetails) Name() string {
 
 func (m *loadGitDetails) Apply(ctx context.Context, b *bundle.Bundle) diag.Diagnostics {
 	// Load relevant git repository
-	repo, err := git.NewRepository(b.RootPath)
+	repo, err := git.NewRepository(vfs.MustNew(b.RootPath))
 	if err != nil {
 		return diag.FromErr(err)
 	}
diff --git a/bundle/config/validate/validate_sync_patterns.go b/bundle/config/validate/validate_sync_patterns.go
index 58acf6ae..832efede 100644
--- a/bundle/config/validate/validate_sync_patterns.go
+++ b/bundle/config/validate/validate_sync_patterns.go
@@ -8,6 +8,7 @@ import (
 	"github.com/databricks/cli/bundle"
 	"github.com/databricks/cli/libs/diag"
 	"github.com/databricks/cli/libs/fileset"
+	"github.com/databricks/cli/libs/vfs"
 	"golang.org/x/sync/errgroup"
 )
 
@@ -50,7 +51,7 @@ func checkPatterns(patterns []string, path string, rb bundle.ReadOnlyBundle) (di
 		index := i
 		p := pattern
 		errs.Go(func() error {
-			fs, err := fileset.NewGlobSet(rb.RootPath(), []string{p})
+			fs, err := fileset.NewGlobSet(vfs.MustNew(rb.RootPath()), []string{p})
 			if err != nil {
 				return err
 			}
diff --git a/bundle/deploy/files/sync.go b/bundle/deploy/files/sync.go
index d78ab2d7..8d6efdae 100644
--- a/bundle/deploy/files/sync.go
+++ b/bundle/deploy/files/sync.go
@@ -6,6 +6,7 @@ import (
 
 	"github.com/databricks/cli/bundle"
 	"github.com/databricks/cli/libs/sync"
+	"github.com/databricks/cli/libs/vfs"
 )
 
 func GetSync(ctx context.Context, rb bundle.ReadOnlyBundle) (*sync.Sync, error) {
@@ -28,7 +29,7 @@ func GetSyncOptions(ctx context.Context, rb bundle.ReadOnlyBundle) (*sync.SyncOp
 	}
 
 	opts := &sync.SyncOptions{
-		LocalPath:  rb.RootPath(),
+		LocalPath:  vfs.MustNew(rb.RootPath()),
 		RemotePath: rb.Config().Workspace.FilePath,
 		Include:    includes,
 		Exclude:    rb.Config().Sync.Exclude,
diff --git a/bundle/deploy/state.go b/bundle/deploy/state.go
index ffcadc9d..ccff64fe 100644
--- a/bundle/deploy/state.go
+++ b/bundle/deploy/state.go
@@ -12,6 +12,7 @@ import (
 
 	"github.com/databricks/cli/bundle"
 	"github.com/databricks/cli/libs/fileset"
+	"github.com/databricks/cli/libs/vfs"
 )
 
 const DeploymentStateFileName = "deployment.json"
@@ -112,12 +113,18 @@ func FromSlice(files []fileset.File) (Filelist, error) {
 
 func (f Filelist) ToSlice(basePath string) []fileset.File {
 	var files []fileset.File
+	root := vfs.MustNew(basePath)
 	for _, file := range f {
-		absPath := filepath.Join(basePath, file.LocalPath)
+		entry := newEntry(filepath.Join(basePath, file.LocalPath))
+
+		// Snapshots created with versions <= v0.220.0 use platform-specific
+		// paths (i.e. with backslashes). Files returned by [libs/fileset] always
+		// contain forward slashes after this version. Normalize before using.
+		relative := filepath.ToSlash(file.LocalPath)
 		if file.IsNotebook {
-			files = append(files, fileset.NewNotebookFile(newEntry(absPath), absPath, file.LocalPath))
+			files = append(files, fileset.NewNotebookFile(root, entry, relative))
 		} else {
-			files = append(files, fileset.NewSourceFile(newEntry(absPath), absPath, file.LocalPath))
+			files = append(files, fileset.NewSourceFile(root, entry, relative))
 		}
 	}
 	return files
diff --git a/bundle/deploy/state_test.go b/bundle/deploy/state_test.go
index 15bdc96b..efa051ab 100644
--- a/bundle/deploy/state_test.go
+++ b/bundle/deploy/state_test.go
@@ -3,17 +3,17 @@ package deploy
 import (
 	"bytes"
 	"encoding/json"
-	"path/filepath"
 	"testing"
 
 	"github.com/databricks/cli/internal/testutil"
 	"github.com/databricks/cli/libs/fileset"
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/require"
 )
 
 func TestFromSlice(t *testing.T) {
 	tmpDir := t.TempDir()
-	fileset := fileset.New(tmpDir)
+	fileset := fileset.New(vfs.MustNew(tmpDir))
 	testutil.Touch(t, tmpDir, "test1.py")
 	testutil.Touch(t, tmpDir, "test2.py")
 	testutil.Touch(t, tmpDir, "test3.py")
@@ -32,7 +32,7 @@ func TestFromSlice(t *testing.T) {
 
 func TestToSlice(t *testing.T) {
 	tmpDir := t.TempDir()
-	fileset := fileset.New(tmpDir)
+	fileset := fileset.New(vfs.MustNew(tmpDir))
 	testutil.Touch(t, tmpDir, "test1.py")
 	testutil.Touch(t, tmpDir, "test2.py")
 	testutil.Touch(t, tmpDir, "test3.py")
@@ -48,18 +48,11 @@ func TestToSlice(t *testing.T) {
 	require.Len(t, s, 3)
 
 	for _, file := range s {
-		require.Contains(t, []string{"test1.py", "test2.py", "test3.py"}, file.Name())
-		require.Contains(t, []string{
-			filepath.Join(tmpDir, "test1.py"),
-			filepath.Join(tmpDir, "test2.py"),
-			filepath.Join(tmpDir, "test3.py"),
-		}, file.Absolute)
-		require.False(t, file.IsDir())
-		require.NotZero(t, file.Type())
-		info, err := file.Info()
-		require.NoError(t, err)
-		require.NotNil(t, info)
-		require.Equal(t, file.Name(), info.Name())
+		require.Contains(t, []string{"test1.py", "test2.py", "test3.py"}, file.Relative)
+
+		// If the mtime is not zero we know we produced a valid fs.DirEntry.
+		ts := file.Modified()
+		require.NotZero(t, ts)
 	}
 }
 
diff --git a/cmd/sync/sync.go b/cmd/sync/sync.go
index 42550722..e5f1bfc9 100644
--- a/cmd/sync/sync.go
+++ b/cmd/sync/sync.go
@@ -14,6 +14,7 @@ import (
 	"github.com/databricks/cli/cmd/root"
 	"github.com/databricks/cli/libs/flags"
 	"github.com/databricks/cli/libs/sync"
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/spf13/cobra"
 )
 
@@ -46,7 +47,7 @@ func (f *syncFlags) syncOptionsFromArgs(cmd *cobra.Command, args []string) (*syn
 	}
 
 	opts := sync.SyncOptions{
-		LocalPath:    args[0],
+		LocalPath:    vfs.MustNew(args[0]),
 		RemotePath:   args[1],
 		Full:         f.full,
 		PollInterval: f.interval,
diff --git a/cmd/sync/sync_test.go b/cmd/sync/sync_test.go
index 026d840f..b741e7b1 100644
--- a/cmd/sync/sync_test.go
+++ b/cmd/sync/sync_test.go
@@ -31,7 +31,7 @@ func TestSyncOptionsFromBundle(t *testing.T) {
 	f := syncFlags{}
 	opts, err := f.syncOptionsFromBundle(New(), []string{}, b)
 	require.NoError(t, err)
-	assert.Equal(t, tempDir, opts.LocalPath)
+	assert.Equal(t, tempDir, opts.LocalPath.Native())
 	assert.Equal(t, "/Users/jane@doe.com/path", opts.RemotePath)
 	assert.Equal(t, filepath.Join(tempDir, ".databricks", "bundle", "default"), opts.SnapshotBasePath)
 	assert.NotNil(t, opts.WorkspaceClient)
@@ -49,11 +49,14 @@ func TestSyncOptionsFromArgsRequiredTwoArgs(t *testing.T) {
 }
 
 func TestSyncOptionsFromArgs(t *testing.T) {
+	local := t.TempDir()
+	remote := "/remote"
+
 	f := syncFlags{}
 	cmd := New()
 	cmd.SetContext(root.SetWorkspaceClient(context.Background(), nil))
-	opts, err := f.syncOptionsFromArgs(cmd, []string{"/local", "/remote"})
+	opts, err := f.syncOptionsFromArgs(cmd, []string{local, remote})
 	require.NoError(t, err)
-	assert.Equal(t, "/local", opts.LocalPath)
-	assert.Equal(t, "/remote", opts.RemotePath)
+	assert.Equal(t, local, opts.LocalPath.Native())
+	assert.Equal(t, remote, opts.RemotePath)
 }
diff --git a/internal/sync_test.go b/internal/sync_test.go
index f970a7ce..4021e649 100644
--- a/internal/sync_test.go
+++ b/internal/sync_test.go
@@ -313,7 +313,7 @@ func TestAccSyncNestedFolderSync(t *testing.T) {
 	assertSync.remoteDirContent(ctx, "dir1", []string{"dir2"})
 	assertSync.remoteDirContent(ctx, "dir1/dir2", []string{"dir3"})
 	assertSync.remoteDirContent(ctx, "dir1/dir2/dir3", []string{"foo.txt"})
-	assertSync.snapshotContains(append(repoFiles, ".gitignore", filepath.FromSlash("dir1/dir2/dir3/foo.txt")))
+	assertSync.snapshotContains(append(repoFiles, ".gitignore", "dir1/dir2/dir3/foo.txt"))
 
 	// delete
 	f.Remove(t)
@@ -374,7 +374,7 @@ func TestAccSyncNestedSpacePlusAndHashAreEscapedSync(t *testing.T) {
 	assertSync.remoteDirContent(ctx, "dir1", []string{"a b+c"})
 	assertSync.remoteDirContent(ctx, "dir1/a b+c", []string{"c+d e"})
 	assertSync.remoteDirContent(ctx, "dir1/a b+c/c+d e", []string{"e+f g#i.txt"})
-	assertSync.snapshotContains(append(repoFiles, ".gitignore", filepath.FromSlash("dir1/a b+c/c+d e/e+f g#i.txt")))
+	assertSync.snapshotContains(append(repoFiles, ".gitignore", "dir1/a b+c/c+d e/e+f g#i.txt"))
 
 	// delete
 	f.Remove(t)
@@ -404,7 +404,7 @@ func TestAccSyncIncrementalFileOverwritesFolder(t *testing.T) {
 	assertSync.waitForCompletionMarker()
 	assertSync.remoteDirContent(ctx, "", append(repoFiles, ".gitignore", "foo"))
 	assertSync.remoteDirContent(ctx, "foo", []string{"bar.txt"})
-	assertSync.snapshotContains(append(repoFiles, ".gitignore", filepath.FromSlash("foo/bar.txt")))
+	assertSync.snapshotContains(append(repoFiles, ".gitignore", "foo/bar.txt"))
 
 	// delete foo/bar.txt
 	f.Remove(t)
diff --git a/libs/fileset/file.go b/libs/fileset/file.go
index 17cae795..fd846b25 100644
--- a/libs/fileset/file.go
+++ b/libs/fileset/file.go
@@ -5,6 +5,7 @@ import (
 	"time"
 
 	"github.com/databricks/cli/libs/notebook"
+	"github.com/databricks/cli/libs/vfs"
 )
 
 type fileType int
@@ -16,40 +17,49 @@ const (
 )
 
 type File struct {
-	fs.DirEntry
-	Absolute, Relative string
-	fileType           fileType
+	// Root path of the fileset.
+	root vfs.Path
+
+	// File entry as returned by the [fs.WalkDir] function.
+	entry fs.DirEntry
+
+	// Type of the file.
+	fileType fileType
+
+	// Relative path within the fileset.
+	// Combine with the [vfs.Path] to interact with the underlying file.
+	Relative string
 }
 
-func NewNotebookFile(entry fs.DirEntry, absolute string, relative string) File {
+func NewNotebookFile(root vfs.Path, entry fs.DirEntry, relative string) File {
 	return File{
-		DirEntry: entry,
-		Absolute: absolute,
-		Relative: relative,
+		root:     root,
+		entry:    entry,
 		fileType: Notebook,
+		Relative: relative,
 	}
 }
 
-func NewFile(entry fs.DirEntry, absolute string, relative string) File {
+func NewFile(root vfs.Path, entry fs.DirEntry, relative string) File {
 	return File{
-		DirEntry: entry,
-		Absolute: absolute,
-		Relative: relative,
+		root:     root,
+		entry:    entry,
 		fileType: Unknown,
+		Relative: relative,
 	}
 }
 
-func NewSourceFile(entry fs.DirEntry, absolute string, relative string) File {
+func NewSourceFile(root vfs.Path, entry fs.DirEntry, relative string) File {
 	return File{
-		DirEntry: entry,
-		Absolute: absolute,
-		Relative: relative,
+		root:     root,
+		entry:    entry,
 		fileType: Source,
+		Relative: relative,
 	}
 }
 
 func (f File) Modified() (ts time.Time) {
-	info, err := f.Info()
+	info, err := f.entry.Info()
 	if err != nil {
 		// return default time, beginning of epoch
 		return ts
@@ -63,7 +73,7 @@ func (f *File) IsNotebook() (bool, error) {
 	}
 
 	// Otherwise, detect the notebook type.
-	isNotebook, _, err := notebook.Detect(f.Absolute)
+	isNotebook, _, err := notebook.DetectWithFS(f.root, f.Relative)
 	if err != nil {
 		return false, err
 	}
diff --git a/libs/fileset/file_test.go b/libs/fileset/file_test.go
index cdfc9ba1..1ce1ff59 100644
--- a/libs/fileset/file_test.go
+++ b/libs/fileset/file_test.go
@@ -1,22 +1,22 @@
 package fileset
 
 import (
-	"path/filepath"
 	"testing"
 
 	"github.com/databricks/cli/internal/testutil"
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/require"
 )
 
 func TestNotebookFileIsNotebook(t *testing.T) {
-	f := NewNotebookFile(nil, "", "")
+	f := NewNotebookFile(nil, nil, "")
 	isNotebook, err := f.IsNotebook()
 	require.NoError(t, err)
 	require.True(t, isNotebook)
 }
 
 func TestSourceFileIsNotNotebook(t *testing.T) {
-	f := NewSourceFile(nil, "", "")
+	f := NewSourceFile(nil, nil, "")
 	isNotebook, err := f.IsNotebook()
 	require.NoError(t, err)
 	require.False(t, isNotebook)
@@ -24,18 +24,19 @@ func TestSourceFileIsNotNotebook(t *testing.T) {
 
 func TestUnknownFileDetectsNotebook(t *testing.T) {
 	tmpDir := t.TempDir()
+	root := vfs.MustNew(tmpDir)
 
 	t.Run("file", func(t *testing.T) {
-		path := testutil.Touch(t, tmpDir, "test.py")
-		f := NewFile(nil, path, filepath.Base(path))
+		testutil.Touch(t, tmpDir, "test.py")
+		f := NewFile(root, nil, "test.py")
 		isNotebook, err := f.IsNotebook()
 		require.NoError(t, err)
 		require.False(t, isNotebook)
 	})
 
 	t.Run("notebook", func(t *testing.T) {
-		path := testutil.TouchNotebook(t, tmpDir, "notebook.py")
-		f := NewFile(nil, path, filepath.Base(path))
+		testutil.TouchNotebook(t, tmpDir, "notebook.py")
+		f := NewFile(root, nil, "notebook.py")
 		isNotebook, err := f.IsNotebook()
 		require.NoError(t, err)
 		require.True(t, isNotebook)
diff --git a/libs/fileset/fileset.go b/libs/fileset/fileset.go
index 52463dff..d0f00f97 100644
--- a/libs/fileset/fileset.go
+++ b/libs/fileset/fileset.go
@@ -4,20 +4,24 @@ import (
 	"fmt"
 	"io/fs"
 	"os"
-	"path/filepath"
+
+	"github.com/databricks/cli/libs/vfs"
 )
 
 // FileSet facilitates fast recursive file listing of a path.
 // It optionally takes into account ignore rules through the [Ignorer] interface.
 type FileSet struct {
-	root   string
+	// Root path of the fileset.
+	root vfs.Path
+
+	// Ignorer interface to check if a file or directory should be ignored.
 	ignore Ignorer
 }
 
 // New returns a [FileSet] for the given root path.
-func New(root string) *FileSet {
+func New(root vfs.Path) *FileSet {
 	return &FileSet{
-		root:   filepath.Clean(root),
+		root:   root,
 		ignore: nopIgnorer{},
 	}
 }
@@ -32,11 +36,6 @@ func (w *FileSet) SetIgnorer(ignore Ignorer) {
 	w.ignore = ignore
 }
 
-// Return root for fileset.
-func (w *FileSet) Root() string {
-	return w.root
-}
-
 // Return all tracked files for Repo
 func (w *FileSet) All() ([]File, error) {
 	return w.recursiveListFiles()
@@ -46,12 +45,7 @@ func (w *FileSet) All() ([]File, error) {
 // that are being tracked in the FileSet (ie not being ignored for matching one of the
 // patterns in w.ignore)
 func (w *FileSet) recursiveListFiles() (fileList []File, err error) {
-	err = filepath.WalkDir(w.root, func(path string, d fs.DirEntry, err error) error {
-		if err != nil {
-			return err
-		}
-
-		relPath, err := filepath.Rel(w.root, path)
+	err = fs.WalkDir(w.root, ".", func(name string, d fs.DirEntry, err error) error {
 		if err != nil {
 			return err
 		}
@@ -66,25 +60,25 @@ func (w *FileSet) recursiveListFiles() (fileList []File, err error) {
 		}
 
 		if d.IsDir() {
-			ign, err := w.ignore.IgnoreDirectory(relPath)
+			ign, err := w.ignore.IgnoreDirectory(name)
 			if err != nil {
-				return fmt.Errorf("cannot check if %s should be ignored: %w", relPath, err)
+				return fmt.Errorf("cannot check if %s should be ignored: %w", name, err)
 			}
 			if ign {
-				return filepath.SkipDir
+				return fs.SkipDir
 			}
 			return nil
 		}
 
-		ign, err := w.ignore.IgnoreFile(relPath)
+		ign, err := w.ignore.IgnoreFile(name)
 		if err != nil {
-			return fmt.Errorf("cannot check if %s should be ignored: %w", relPath, err)
+			return fmt.Errorf("cannot check if %s should be ignored: %w", name, err)
 		}
 		if ign {
 			return nil
 		}
 
-		fileList = append(fileList, NewFile(d, path, relPath))
+		fileList = append(fileList, NewFile(w.root, d, name))
 		return nil
 	})
 	return
diff --git a/libs/fileset/glob.go b/libs/fileset/glob.go
index 9d8626e5..0a103847 100644
--- a/libs/fileset/glob.go
+++ b/libs/fileset/glob.go
@@ -1,22 +1,17 @@
 package fileset
 
 import (
-	"path/filepath"
+	"path"
+
+	"github.com/databricks/cli/libs/vfs"
 )
 
-func NewGlobSet(root string, includes []string) (*FileSet, error) {
-	absRoot, err := filepath.Abs(root)
-	if err != nil {
-		return nil, err
-	}
-
+func NewGlobSet(root vfs.Path, includes []string) (*FileSet, error) {
 	for k := range includes {
-		includes[k] = filepath.ToSlash(filepath.Clean(includes[k]))
+		includes[k] = path.Clean(includes[k])
 	}
 
-	fs := &FileSet{
-		absRoot,
-		newIncluder(includes),
-	}
+	fs := New(root)
+	fs.SetIgnorer(newIncluder(includes))
 	return fs, nil
 }
diff --git a/libs/fileset/glob_test.go b/libs/fileset/glob_test.go
index e8d3696c..70b9c444 100644
--- a/libs/fileset/glob_test.go
+++ b/libs/fileset/glob_test.go
@@ -2,21 +2,26 @@ package fileset
 
 import (
 	"io/fs"
-	"os"
-	"path/filepath"
+	"path"
 	"slices"
 	"strings"
 	"testing"
 
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/require"
 )
 
-func TestGlobFileset(t *testing.T) {
-	cwd, err := os.Getwd()
-	require.NoError(t, err)
-	root := filepath.Join(cwd, "..", "filer")
+func collectRelativePaths(files []File) []string {
+	relativePaths := make([]string, 0)
+	for _, f := range files {
+		relativePaths = append(relativePaths, f.Relative)
+	}
+	return relativePaths
+}
 
-	entries, err := os.ReadDir(root)
+func TestGlobFileset(t *testing.T) {
+	root := vfs.MustNew("../filer")
+	entries, err := root.ReadDir(".")
 	require.NoError(t, err)
 
 	g, err := NewGlobSet(root, []string{
@@ -30,7 +35,7 @@ func TestGlobFileset(t *testing.T) {
 	require.Equal(t, len(files), len(entries))
 	for _, f := range files {
 		exists := slices.ContainsFunc(entries, func(de fs.DirEntry) bool {
-			return de.Name() == f.Name()
+			return de.Name() == path.Base(f.Relative)
 		})
 		require.True(t, exists)
 	}
@@ -46,9 +51,8 @@ func TestGlobFileset(t *testing.T) {
 }
 
 func TestGlobFilesetWithRelativeRoot(t *testing.T) {
-	root := filepath.Join("..", "filer")
-
-	entries, err := os.ReadDir(root)
+	root := vfs.MustNew("../filer")
+	entries, err := root.ReadDir(".")
 	require.NoError(t, err)
 
 	g, err := NewGlobSet(root, []string{
@@ -58,21 +62,14 @@ func TestGlobFilesetWithRelativeRoot(t *testing.T) {
 
 	files, err := g.All()
 	require.NoError(t, err)
-
 	require.Equal(t, len(files), len(entries))
-	for _, f := range files {
-		require.True(t, filepath.IsAbs(f.Absolute))
-	}
 }
 
 func TestGlobFilesetRecursively(t *testing.T) {
-	cwd, err := os.Getwd()
-	require.NoError(t, err)
-	root := filepath.Join(cwd, "..", "git")
-
+	root := vfs.MustNew("../git")
 	entries := make([]string, 0)
-	err = filepath.Walk(filepath.Join(root, "testdata"), func(path string, info fs.FileInfo, err error) error {
-		if !info.IsDir() {
+	err := fs.WalkDir(root, "testdata", func(path string, d fs.DirEntry, err error) error {
+		if !d.IsDir() {
 			entries = append(entries, path)
 		}
 		return nil
@@ -86,24 +83,14 @@ func TestGlobFilesetRecursively(t *testing.T) {
 
 	files, err := g.All()
 	require.NoError(t, err)
-
-	require.Equal(t, len(files), len(entries))
-	for _, f := range files {
-		exists := slices.ContainsFunc(entries, func(path string) bool {
-			return path == f.Absolute
-		})
-		require.True(t, exists)
-	}
+	require.ElementsMatch(t, entries, collectRelativePaths(files))
 }
 
 func TestGlobFilesetDir(t *testing.T) {
-	cwd, err := os.Getwd()
-	require.NoError(t, err)
-	root := filepath.Join(cwd, "..", "git")
-
+	root := vfs.MustNew("../git")
 	entries := make([]string, 0)
-	err = filepath.Walk(filepath.Join(root, "testdata", "a"), func(path string, info fs.FileInfo, err error) error {
-		if !info.IsDir() {
+	err := fs.WalkDir(root, "testdata/a", func(path string, d fs.DirEntry, err error) error {
+		if !d.IsDir() {
 			entries = append(entries, path)
 		}
 		return nil
@@ -117,23 +104,13 @@ func TestGlobFilesetDir(t *testing.T) {
 
 	files, err := g.All()
 	require.NoError(t, err)
-
-	require.Equal(t, len(files), len(entries))
-	for _, f := range files {
-		exists := slices.ContainsFunc(entries, func(path string) bool {
-			return path == f.Absolute
-		})
-		require.True(t, exists)
-	}
+	require.ElementsMatch(t, entries, collectRelativePaths(files))
 }
 
 func TestGlobFilesetDoubleQuotesWithFilePatterns(t *testing.T) {
-	cwd, err := os.Getwd()
-	require.NoError(t, err)
-	root := filepath.Join(cwd, "..", "git")
-
+	root := vfs.MustNew("../git")
 	entries := make([]string, 0)
-	err = filepath.Walk(filepath.Join(root, "testdata"), func(path string, info fs.FileInfo, err error) error {
+	err := fs.WalkDir(root, "testdata", func(path string, d fs.DirEntry, err error) error {
 		if strings.HasSuffix(path, ".txt") {
 			entries = append(entries, path)
 		}
@@ -148,12 +125,5 @@ func TestGlobFilesetDoubleQuotesWithFilePatterns(t *testing.T) {
 
 	files, err := g.All()
 	require.NoError(t, err)
-
-	require.Equal(t, len(files), len(entries))
-	for _, f := range files {
-		exists := slices.ContainsFunc(entries, func(path string) bool {
-			return path == f.Absolute
-		})
-		require.True(t, exists)
-	}
+	require.ElementsMatch(t, entries, collectRelativePaths(files))
 }
diff --git a/libs/git/config.go b/libs/git/config.go
index e83c75b7..424d453b 100644
--- a/libs/git/config.go
+++ b/libs/git/config.go
@@ -8,6 +8,7 @@ import (
 	"regexp"
 	"strings"
 
+	"github.com/databricks/cli/libs/vfs"
 	"gopkg.in/ini.v1"
 )
 
@@ -87,8 +88,8 @@ func (c config) load(r io.Reader) error {
 	return nil
 }
 
-func (c config) loadFile(path string) error {
-	f, err := os.Open(path)
+func (c config) loadFile(fs vfs.Path, path string) error {
+	f, err := fs.Open(path)
 	if err != nil {
 		// If the file doesn't exist it is ignored.
 		// This is the case for both global and repository specific config files.
@@ -152,8 +153,8 @@ func globalGitConfig() (*config, error) {
 	// > are missing or unreadable they will be ignored.
 	//
 	// We therefore ignore the error return value for the calls below.
-	config.loadFile(filepath.Join(xdgConfigHome, "git/config"))
-	config.loadFile(filepath.Join(config.home, ".gitconfig"))
+	config.loadFile(vfs.MustNew(xdgConfigHome), "git/config")
+	config.loadFile(vfs.MustNew(config.home), ".gitconfig")
 
 	return config, nil
 }
diff --git a/libs/git/fileset.go b/libs/git/fileset.go
index c604ac7f..f1986aa2 100644
--- a/libs/git/fileset.go
+++ b/libs/git/fileset.go
@@ -2,6 +2,7 @@ package git
 
 import (
 	"github.com/databricks/cli/libs/fileset"
+	"github.com/databricks/cli/libs/vfs"
 )
 
 // FileSet is Git repository aware implementation of [fileset.FileSet].
@@ -13,7 +14,7 @@ type FileSet struct {
 }
 
 // NewFileSet returns [FileSet] for the Git repository located at `root`.
-func NewFileSet(root string) (*FileSet, error) {
+func NewFileSet(root vfs.Path) (*FileSet, error) {
 	fs := fileset.New(root)
 	v, err := NewView(root)
 	if err != nil {
@@ -34,10 +35,6 @@ func (f *FileSet) IgnoreDirectory(dir string) (bool, error) {
 	return f.view.IgnoreDirectory(dir)
 }
 
-func (f *FileSet) Root() string {
-	return f.fileset.Root()
-}
-
 func (f *FileSet) All() ([]fileset.File, error) {
 	f.view.repo.taintIgnoreRules()
 	return f.fileset.All()
diff --git a/libs/git/fileset_test.go b/libs/git/fileset_test.go
index 74133f52..4e6172bf 100644
--- a/libs/git/fileset_test.go
+++ b/libs/git/fileset_test.go
@@ -2,23 +2,25 @@ package git
 
 import (
 	"os"
+	"path"
 	"path/filepath"
 	"strings"
 	"testing"
 
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
 
-func testFileSetAll(t *testing.T, path string) {
-	fileSet, err := NewFileSet(path)
+func testFileSetAll(t *testing.T, root string) {
+	fileSet, err := NewFileSet(vfs.MustNew(root))
 	require.NoError(t, err)
 	files, err := fileSet.All()
 	require.NoError(t, err)
 	require.Len(t, files, 3)
-	assert.Equal(t, filepath.Join("a", "b", "world.txt"), files[0].Relative)
-	assert.Equal(t, filepath.Join("a", "hello.txt"), files[1].Relative)
-	assert.Equal(t, filepath.Join("databricks.yml"), files[2].Relative)
+	assert.Equal(t, path.Join("a", "b", "world.txt"), files[0].Relative)
+	assert.Equal(t, path.Join("a", "hello.txt"), files[1].Relative)
+	assert.Equal(t, path.Join("databricks.yml"), files[2].Relative)
 }
 
 func TestFileSetListAllInRepo(t *testing.T) {
@@ -33,7 +35,7 @@ func TestFileSetNonCleanRoot(t *testing.T) {
 	// Test what happens if the root directory can be simplified.
 	// Path simplification is done by most filepath functions.
 	// This should yield the same result as above test.
-	fileSet, err := NewFileSet("./testdata/../testdata")
+	fileSet, err := NewFileSet(vfs.MustNew("./testdata/../testdata"))
 	require.NoError(t, err)
 	files, err := fileSet.All()
 	require.NoError(t, err)
@@ -42,7 +44,7 @@ func TestFileSetNonCleanRoot(t *testing.T) {
 
 func TestFileSetAddsCacheDirToGitIgnore(t *testing.T) {
 	projectDir := t.TempDir()
-	fileSet, err := NewFileSet(projectDir)
+	fileSet, err := NewFileSet(vfs.MustNew(projectDir))
 	require.NoError(t, err)
 	fileSet.EnsureValidGitIgnoreExists()
 
@@ -57,7 +59,7 @@ func TestFileSetDoesNotCacheDirToGitIgnoreIfAlreadyPresent(t *testing.T) {
 	projectDir := t.TempDir()
 	gitIgnorePath := filepath.Join(projectDir, ".gitignore")
 
-	fileSet, err := NewFileSet(projectDir)
+	fileSet, err := NewFileSet(vfs.MustNew(projectDir))
 	require.NoError(t, err)
 	err = os.WriteFile(gitIgnorePath, []byte(".databricks"), 0o644)
 	require.NoError(t, err)
diff --git a/libs/git/ignore.go b/libs/git/ignore.go
index ec66a2b2..df3a4e91 100644
--- a/libs/git/ignore.go
+++ b/libs/git/ignore.go
@@ -1,9 +1,12 @@
 package git
 
 import (
+	"io/fs"
 	"os"
+	"strings"
 	"time"
 
+	"github.com/databricks/cli/libs/vfs"
 	ignore "github.com/sabhiram/go-gitignore"
 )
 
@@ -21,7 +24,8 @@ type ignoreRules interface {
 // ignoreFile represents a gitignore file backed by a path.
 // If the path doesn't exist (yet), it is treated as an empty file.
 type ignoreFile struct {
-	absPath string
+	root vfs.Path
+	path string
 
 	// Signal a reload of this file.
 	// Set this to call [os.Stat] and a potential reload
@@ -35,9 +39,10 @@ type ignoreFile struct {
 	patterns *ignore.GitIgnore
 }
 
-func newIgnoreFile(absPath string) ignoreRules {
+func newIgnoreFile(root vfs.Path, path string) ignoreRules {
 	return &ignoreFile{
-		absPath:        absPath,
+		root:           root,
+		path:           path,
 		checkForReload: true,
 	}
 }
@@ -67,7 +72,7 @@ func (f *ignoreFile) Taint() {
 func (f *ignoreFile) load() error {
 	// The file must be stat-able.
 	// If it doesn't exist, treat it as an empty file.
-	stat, err := os.Stat(f.absPath)
+	stat, err := fs.Stat(f.root, f.path)
 	if err != nil {
 		if os.IsNotExist(err) {
 			return nil
@@ -82,7 +87,7 @@ func (f *ignoreFile) load() error {
 	}
 
 	f.modTime = stat.ModTime()
-	f.patterns, err = ignore.CompileIgnoreFile(f.absPath)
+	f.patterns, err = f.loadGitignore()
 	if err != nil {
 		return err
 	}
@@ -90,6 +95,16 @@ func (f *ignoreFile) load() error {
 	return nil
 }
 
+func (f *ignoreFile) loadGitignore() (*ignore.GitIgnore, error) {
+	data, err := fs.ReadFile(f.root, f.path)
+	if err != nil {
+		return nil, err
+	}
+
+	lines := strings.Split(string(data), "\n")
+	return ignore.CompileIgnoreLines(lines...), nil
+}
+
 // stringIgnoreRules implements the [ignoreRules] interface
 // for a set of in-memory ignore patterns.
 type stringIgnoreRules struct {
diff --git a/libs/git/ignore_test.go b/libs/git/ignore_test.go
index 160f53d7..057c0cb2 100644
--- a/libs/git/ignore_test.go
+++ b/libs/git/ignore_test.go
@@ -5,6 +5,7 @@ import (
 	"path/filepath"
 	"testing"
 
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
@@ -13,7 +14,7 @@ func TestIgnoreFile(t *testing.T) {
 	var ign bool
 	var err error
 
-	f := newIgnoreFile("./testdata/.gitignore")
+	f := newIgnoreFile(vfs.MustNew("testdata"), ".gitignore")
 	ign, err = f.MatchesPath("root.foo")
 	require.NoError(t, err)
 	assert.True(t, ign)
@@ -27,7 +28,7 @@ func TestIgnoreFileDoesntExist(t *testing.T) {
 	var err error
 
 	// Files that don't exist are treated as an empty gitignore file.
-	f := newIgnoreFile("./testdata/thispathdoesntexist")
+	f := newIgnoreFile(vfs.MustNew("testdata"), "thispathdoesntexist")
 	ign, err = f.MatchesPath("i'm included")
 	require.NoError(t, err)
 	assert.False(t, ign)
@@ -41,7 +42,7 @@ func TestIgnoreFileTaint(t *testing.T) {
 	gitIgnorePath := filepath.Join(tempDir, ".gitignore")
 
 	// Files that don't exist are treated as an empty gitignore file.
-	f := newIgnoreFile(gitIgnorePath)
+	f := newIgnoreFile(vfs.MustNew(tempDir), ".gitignore")
 	ign, err = f.MatchesPath("hello")
 	require.NoError(t, err)
 	assert.False(t, ign)
diff --git a/libs/git/reference.go b/libs/git/reference.go
index 4021f2e6..2b4bd3e4 100644
--- a/libs/git/reference.go
+++ b/libs/git/reference.go
@@ -2,10 +2,12 @@ package git
 
 import (
 	"fmt"
+	"io/fs"
 	"os"
-	"path/filepath"
 	"regexp"
 	"strings"
+
+	"github.com/databricks/cli/libs/vfs"
 )
 
 type ReferenceType string
@@ -37,9 +39,9 @@ func isSHA1(s string) bool {
 	return re.MatchString(s)
 }
 
-func LoadReferenceFile(path string) (*Reference, error) {
+func LoadReferenceFile(root vfs.Path, path string) (*Reference, error) {
 	// read reference file content
-	b, err := os.ReadFile(path)
+	b, err := fs.ReadFile(root, path)
 	if os.IsNotExist(err) {
 		return nil, nil
 	}
@@ -73,8 +75,7 @@ func (ref *Reference) ResolvePath() (string, error) {
 	if ref.Type != ReferenceTypePointer {
 		return "", ErrNotAReferencePointer
 	}
-	refPath := strings.TrimPrefix(ref.Content, ReferencePrefix)
-	return filepath.FromSlash(refPath), nil
+	return strings.TrimPrefix(ref.Content, ReferencePrefix), nil
 }
 
 // resolves the name of the current branch from the reference file content. For example
@@ -87,8 +88,6 @@ func (ref *Reference) CurrentBranch() (string, error) {
 	if err != nil {
 		return "", err
 	}
-	// normalize branch ref path to work accross different operating systems
-	branchRefPath = filepath.ToSlash(branchRefPath)
 	if !strings.HasPrefix(branchRefPath, HeadPathPrefix) {
 		return "", fmt.Errorf("reference path %s does not have expected prefix %s", branchRefPath, HeadPathPrefix)
 	}
diff --git a/libs/git/reference_test.go b/libs/git/reference_test.go
index 1b08e989..194d7933 100644
--- a/libs/git/reference_test.go
+++ b/libs/git/reference_test.go
@@ -6,6 +6,7 @@ import (
 	"strings"
 	"testing"
 
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
@@ -45,7 +46,7 @@ func TestReferenceReferencePathForReference(t *testing.T) {
 	}
 	path, err := ref.ResolvePath()
 	assert.NoError(t, err)
-	assert.Equal(t, filepath.FromSlash("refs/heads/my-branch"), path)
+	assert.Equal(t, "refs/heads/my-branch", path)
 }
 
 func TestReferenceLoadingForObjectID(t *testing.T) {
@@ -55,7 +56,7 @@ func TestReferenceLoadingForObjectID(t *testing.T) {
 	defer f.Close()
 	f.WriteString(strings.Repeat("e", 40) + "\r\n")
 
-	ref, err := LoadReferenceFile(filepath.Join(tmp, "HEAD"))
+	ref, err := LoadReferenceFile(vfs.MustNew(tmp), "HEAD")
 	assert.NoError(t, err)
 	assert.Equal(t, ReferenceTypeSHA1, ref.Type)
 	assert.Equal(t, strings.Repeat("e", 40), ref.Content)
@@ -68,7 +69,7 @@ func TestReferenceLoadingForReference(t *testing.T) {
 	defer f.Close()
 	f.WriteString("ref: refs/heads/foo\n")
 
-	ref, err := LoadReferenceFile(filepath.Join(tmp, "HEAD"))
+	ref, err := LoadReferenceFile(vfs.MustNew(tmp), "HEAD")
 	assert.NoError(t, err)
 	assert.Equal(t, ReferenceTypePointer, ref.Type)
 	assert.Equal(t, "ref: refs/heads/foo", ref.Content)
@@ -81,7 +82,7 @@ func TestReferenceLoadingFailsForInvalidContent(t *testing.T) {
 	defer f.Close()
 	f.WriteString("abc")
 
-	_, err = LoadReferenceFile(filepath.Join(tmp, "HEAD"))
+	_, err = LoadReferenceFile(vfs.MustNew(tmp), "HEAD")
 	assert.ErrorContains(t, err, "unknown format for git HEAD")
 }
 
diff --git a/libs/git/repository.go b/libs/git/repository.go
index 531fd74e..6baf26c2 100644
--- a/libs/git/repository.go
+++ b/libs/git/repository.go
@@ -7,7 +7,7 @@ import (
 	"path/filepath"
 	"strings"
 
-	"github.com/databricks/cli/libs/folders"
+	"github.com/databricks/cli/libs/vfs"
 )
 
 const gitIgnoreFileName = ".gitignore"
@@ -21,8 +21,8 @@ type Repository struct {
 	// directory where we process .gitignore files.
 	real bool
 
-	// rootPath is the absolute path to the repository root.
-	rootPath string
+	// root is the absolute path to the repository root.
+	root vfs.Path
 
 	// ignore contains a list of ignore patterns indexed by the
 	// path prefix relative to the repository root.
@@ -42,12 +42,12 @@ type Repository struct {
 
 // Root returns the absolute path to the repository root.
 func (r *Repository) Root() string {
-	return r.rootPath
+	return r.root.Native()
 }
 
 func (r *Repository) CurrentBranch() (string, error) {
 	// load .git/HEAD
-	ref, err := LoadReferenceFile(filepath.Join(r.rootPath, GitDirectoryName, "HEAD"))
+	ref, err := LoadReferenceFile(r.root, path.Join(GitDirectoryName, "HEAD"))
 	if err != nil {
 		return "", err
 	}
@@ -64,7 +64,7 @@ func (r *Repository) CurrentBranch() (string, error) {
 
 func (r *Repository) LatestCommit() (string, error) {
 	// load .git/HEAD
-	ref, err := LoadReferenceFile(filepath.Join(r.rootPath, GitDirectoryName, "HEAD"))
+	ref, err := LoadReferenceFile(r.root, path.Join(GitDirectoryName, "HEAD"))
 	if err != nil {
 		return "", err
 	}
@@ -83,7 +83,7 @@ func (r *Repository) LatestCommit() (string, error) {
 	if err != nil {
 		return "", err
 	}
-	branchHeadRef, err := LoadReferenceFile(filepath.Join(r.rootPath, GitDirectoryName, branchHeadPath))
+	branchHeadRef, err := LoadReferenceFile(r.root, path.Join(GitDirectoryName, branchHeadPath))
 	if err != nil {
 		return "", err
 	}
@@ -108,7 +108,7 @@ func (r *Repository) loadConfig() error {
 	if err != nil {
 		return fmt.Errorf("unable to load user specific gitconfig: %w", err)
 	}
-	err = config.loadFile(filepath.Join(r.rootPath, ".git/config"))
+	err = config.loadFile(r.root, ".git/config")
 	if err != nil {
 		return fmt.Errorf("unable to load repository specific gitconfig: %w", err)
 	}
@@ -119,7 +119,7 @@ func (r *Repository) loadConfig() error {
 // newIgnoreFile constructs a new [ignoreRules] implementation backed by
 // a file using the specified path relative to the repository root.
 func (r *Repository) newIgnoreFile(relativeIgnoreFilePath string) ignoreRules {
-	return newIgnoreFile(filepath.Join(r.rootPath, relativeIgnoreFilePath))
+	return newIgnoreFile(r.root, relativeIgnoreFilePath)
 }
 
 // getIgnoreRules returns a slice of [ignoreRules] that apply
@@ -132,7 +132,7 @@ func (r *Repository) getIgnoreRules(prefix string) []ignoreRules {
 		return fs
 	}
 
-	r.ignore[prefix] = append(r.ignore[prefix], r.newIgnoreFile(filepath.Join(prefix, gitIgnoreFileName)))
+	r.ignore[prefix] = append(r.ignore[prefix], r.newIgnoreFile(path.Join(prefix, gitIgnoreFileName)))
 	return r.ignore[prefix]
 }
 
@@ -149,7 +149,7 @@ func (r *Repository) taintIgnoreRules() {
 // Ignore computes whether to ignore the specified path.
 // The specified path is relative to the repository root path.
 func (r *Repository) Ignore(relPath string) (bool, error) {
-	parts := strings.Split(filepath.ToSlash(relPath), "/")
+	parts := strings.Split(relPath, "/")
 
 	// Retain trailing slash for directory patterns.
 	// We know a trailing slash was present if the last element
@@ -186,14 +186,9 @@ func (r *Repository) Ignore(relPath string) (bool, error) {
 	return false, nil
 }
 
-func NewRepository(path string) (*Repository, error) {
-	path, err := filepath.Abs(path)
-	if err != nil {
-		return nil, err
-	}
-
+func NewRepository(path vfs.Path) (*Repository, error) {
 	real := true
-	rootPath, err := folders.FindDirWithLeaf(path, GitDirectoryName)
+	rootPath, err := vfs.FindLeafInTree(path, GitDirectoryName)
 	if err != nil {
 		if !os.IsNotExist(err) {
 			return nil, err
@@ -205,9 +200,9 @@ func NewRepository(path string) (*Repository, error) {
 	}
 
 	repo := &Repository{
-		real:     real,
-		rootPath: rootPath,
-		ignore:   make(map[string][]ignoreRules),
+		real:   real,
+		root:   rootPath,
+		ignore: make(map[string][]ignoreRules),
 	}
 
 	err = repo.loadConfig()
@@ -221,13 +216,21 @@ func NewRepository(path string) (*Repository, error) {
 		return nil, fmt.Errorf("unable to access core excludes file: %w", err)
 	}
 
+	// Load global excludes on this machine.
+	// This is by definition a local path so we create a new [vfs.Path] instance.
+	coreExcludes := newStringIgnoreRules([]string{})
+	if coreExcludesPath != "" {
+		dir := filepath.Dir(coreExcludesPath)
+		base := filepath.Base(coreExcludesPath)
+		coreExcludes = newIgnoreFile(vfs.MustNew(dir), base)
+	}
+
 	// Initialize root ignore rules.
 	// These are special and not lazily initialized because:
 	// 1) we include a hardcoded ignore pattern
 	// 2) we include a gitignore file at a non-standard path
 	repo.ignore["."] = []ignoreRules{
-		// Load global excludes on this machine.
-		newIgnoreFile(coreExcludesPath),
+		coreExcludes,
 		// Always ignore root .git directory.
 		newStringIgnoreRules([]string{
 			".git",
diff --git a/libs/git/repository_test.go b/libs/git/repository_test.go
index fb0e3808..7ddc7ea7 100644
--- a/libs/git/repository_test.go
+++ b/libs/git/repository_test.go
@@ -7,6 +7,7 @@ import (
 	"strings"
 	"testing"
 
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
@@ -43,7 +44,7 @@ func newTestRepository(t *testing.T) *testRepository {
 	_, err = f2.WriteString(`ref: refs/heads/main`)
 	require.NoError(t, err)
 
-	repo, err := NewRepository(tmp)
+	repo, err := NewRepository(vfs.MustNew(tmp))
 	require.NoError(t, err)
 
 	return &testRepository{
@@ -53,7 +54,7 @@ func newTestRepository(t *testing.T) *testRepository {
 }
 
 func (testRepo *testRepository) checkoutCommit(commitId string) {
-	f, err := os.OpenFile(filepath.Join(testRepo.r.rootPath, ".git", "HEAD"), os.O_WRONLY|os.O_TRUNC, os.ModePerm)
+	f, err := os.OpenFile(filepath.Join(testRepo.r.Root(), ".git", "HEAD"), os.O_WRONLY|os.O_TRUNC, os.ModePerm)
 	require.NoError(testRepo.t, err)
 	defer f.Close()
 
@@ -63,7 +64,7 @@ func (testRepo *testRepository) checkoutCommit(commitId string) {
 
 func (testRepo *testRepository) addBranch(name string, latestCommit string) {
 	// create dir for branch head reference
-	branchDir := filepath.Join(testRepo.r.rootPath, ".git", "refs", "heads")
+	branchDir := filepath.Join(testRepo.r.Root(), ".git", "refs", "heads")
 	err := os.MkdirAll(branchDir, os.ModePerm)
 	require.NoError(testRepo.t, err)
 
@@ -78,7 +79,7 @@ func (testRepo *testRepository) addBranch(name string, latestCommit string) {
 }
 
 func (testRepo *testRepository) checkoutBranch(name string) {
-	f, err := os.OpenFile(filepath.Join(testRepo.r.rootPath, ".git", "HEAD"), os.O_WRONLY|os.O_TRUNC, os.ModePerm)
+	f, err := os.OpenFile(filepath.Join(testRepo.r.Root(), ".git", "HEAD"), os.O_WRONLY|os.O_TRUNC, os.ModePerm)
 	require.NoError(testRepo.t, err)
 	defer f.Close()
 
@@ -89,7 +90,7 @@ func (testRepo *testRepository) checkoutBranch(name string) {
 // add remote origin url to test repo
 func (testRepo *testRepository) addOriginUrl(url string) {
 	// open config in append mode
-	f, err := os.OpenFile(filepath.Join(testRepo.r.rootPath, ".git", "config"), os.O_WRONLY|os.O_APPEND, os.ModePerm)
+	f, err := os.OpenFile(filepath.Join(testRepo.r.Root(), ".git", "config"), os.O_WRONLY|os.O_APPEND, os.ModePerm)
 	require.NoError(testRepo.t, err)
 	defer f.Close()
 
@@ -128,7 +129,7 @@ func (testRepo *testRepository) assertOriginUrl(expected string) {
 
 func TestRepository(t *testing.T) {
 	// Load this repository as test.
-	repo, err := NewRepository("../..")
+	repo, err := NewRepository(vfs.MustNew("../.."))
 	tr := testRepository{t, repo}
 	require.NoError(t, err)
 
@@ -142,7 +143,7 @@ func TestRepository(t *testing.T) {
 	assert.True(t, tr.Ignore("vendor/"))
 
 	// Check that ignores under testdata work.
-	assert.True(t, tr.Ignore(filepath.Join("libs", "git", "testdata", "root.ignoreme")))
+	assert.True(t, tr.Ignore("libs/git/testdata/root.ignoreme"))
 }
 
 func TestRepositoryGitConfigForEmptyRepo(t *testing.T) {
@@ -192,7 +193,7 @@ func TestRepositoryGitConfigForSshUrl(t *testing.T) {
 
 func TestRepositoryGitConfigWhenNotARepo(t *testing.T) {
 	tmp := t.TempDir()
-	repo, err := NewRepository(tmp)
+	repo, err := NewRepository(vfs.MustNew(tmp))
 	require.NoError(t, err)
 
 	branch, err := repo.CurrentBranch()
diff --git a/libs/git/view.go b/libs/git/view.go
index 3cb88d8b..90eed0bb 100644
--- a/libs/git/view.go
+++ b/libs/git/view.go
@@ -1,9 +1,13 @@
 package git
 
 import (
+	"fmt"
 	"os"
+	"path"
 	"path/filepath"
 	"strings"
+
+	"github.com/databricks/cli/libs/vfs"
 )
 
 // View represents a view on a directory tree that takes into account
@@ -29,17 +33,15 @@ type View struct {
 
 // Ignore computes whether to ignore the specified path.
 // The specified path is relative to the view's target path.
-func (v *View) Ignore(path string) (bool, error) {
-	path = filepath.ToSlash(path)
-
+func (v *View) Ignore(relPath string) (bool, error) {
 	// Retain trailing slash for directory patterns.
 	// Needs special handling because it is removed by path cleaning.
 	trailingSlash := ""
-	if strings.HasSuffix(path, "/") {
+	if strings.HasSuffix(relPath, "/") {
 		trailingSlash = "/"
 	}
 
-	return v.repo.Ignore(filepath.Join(v.targetPath, path) + trailingSlash)
+	return v.repo.Ignore(path.Join(v.targetPath, relPath) + trailingSlash)
 }
 
 // IgnoreFile returns if the gitignore rules in this fileset
@@ -70,26 +72,27 @@ func (v *View) IgnoreDirectory(dir string) (bool, error) {
 	return v.Ignore(dir + "/")
 }
 
-func NewView(path string) (*View, error) {
-	path, err := filepath.Abs(path)
-	if err != nil {
-		return nil, err
-	}
-
-	repo, err := NewRepository(path)
+func NewView(root vfs.Path) (*View, error) {
+	repo, err := NewRepository(root)
 	if err != nil {
 		return nil, err
 	}
 
 	// Target path must be relative to the repository root path.
-	targetPath, err := filepath.Rel(repo.rootPath, path)
-	if err != nil {
-		return nil, err
+	target := root.Native()
+	prefix := repo.root.Native()
+	if !strings.HasPrefix(target, prefix) {
+		return nil, fmt.Errorf("path %q is not within repository root %q", root.Native(), prefix)
 	}
 
+	// Make target a relative path.
+	target = strings.TrimPrefix(target, prefix)
+	target = strings.TrimPrefix(target, string(os.PathSeparator))
+	target = path.Clean(filepath.ToSlash(target))
+
 	return &View{
 		repo:       repo,
-		targetPath: targetPath,
+		targetPath: target,
 	}, nil
 }
 
diff --git a/libs/git/view_test.go b/libs/git/view_test.go
index 3ecd301b..76fba345 100644
--- a/libs/git/view_test.go
+++ b/libs/git/view_test.go
@@ -7,6 +7,7 @@ import (
 	"path/filepath"
 	"testing"
 
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
@@ -89,19 +90,19 @@ func testViewAtRoot(t *testing.T, tv testView) {
 }
 
 func TestViewRootInBricksRepo(t *testing.T) {
-	v, err := NewView("./testdata")
+	v, err := NewView(vfs.MustNew("./testdata"))
 	require.NoError(t, err)
 	testViewAtRoot(t, testView{t, v})
 }
 
 func TestViewRootInTempRepo(t *testing.T) {
-	v, err := NewView(createFakeRepo(t, "testdata"))
+	v, err := NewView(vfs.MustNew(createFakeRepo(t, "testdata")))
 	require.NoError(t, err)
 	testViewAtRoot(t, testView{t, v})
 }
 
 func TestViewRootInTempDir(t *testing.T) {
-	v, err := NewView(copyTestdata(t, "testdata"))
+	v, err := NewView(vfs.MustNew(copyTestdata(t, "testdata")))
 	require.NoError(t, err)
 	testViewAtRoot(t, testView{t, v})
 }
@@ -124,20 +125,20 @@ func testViewAtA(t *testing.T, tv testView) {
 }
 
 func TestViewAInBricksRepo(t *testing.T) {
-	v, err := NewView("./testdata/a")
+	v, err := NewView(vfs.MustNew("./testdata/a"))
 	require.NoError(t, err)
 	testViewAtA(t, testView{t, v})
 }
 
 func TestViewAInTempRepo(t *testing.T) {
-	v, err := NewView(filepath.Join(createFakeRepo(t, "testdata"), "a"))
+	v, err := NewView(vfs.MustNew(filepath.Join(createFakeRepo(t, "testdata"), "a")))
 	require.NoError(t, err)
 	testViewAtA(t, testView{t, v})
 }
 
 func TestViewAInTempDir(t *testing.T) {
 	// Since this is not a fake repo it should not traverse up the tree.
-	v, err := NewView(filepath.Join(copyTestdata(t, "testdata"), "a"))
+	v, err := NewView(vfs.MustNew(filepath.Join(copyTestdata(t, "testdata"), "a")))
 	require.NoError(t, err)
 	tv := testView{t, v}
 
@@ -174,20 +175,20 @@ func testViewAtAB(t *testing.T, tv testView) {
 }
 
 func TestViewABInBricksRepo(t *testing.T) {
-	v, err := NewView("./testdata/a/b")
+	v, err := NewView(vfs.MustNew("./testdata/a/b"))
 	require.NoError(t, err)
 	testViewAtAB(t, testView{t, v})
 }
 
 func TestViewABInTempRepo(t *testing.T) {
-	v, err := NewView(filepath.Join(createFakeRepo(t, "testdata"), "a", "b"))
+	v, err := NewView(vfs.MustNew(filepath.Join(createFakeRepo(t, "testdata"), "a", "b")))
 	require.NoError(t, err)
 	testViewAtAB(t, testView{t, v})
 }
 
 func TestViewABInTempDir(t *testing.T) {
 	// Since this is not a fake repo it should not traverse up the tree.
-	v, err := NewView(filepath.Join(copyTestdata(t, "testdata"), "a", "b"))
+	v, err := NewView(vfs.MustNew(filepath.Join(copyTestdata(t, "testdata"), "a", "b")))
 	tv := testView{t, v}
 	require.NoError(t, err)
 
@@ -214,7 +215,7 @@ func TestViewDoesNotChangeGitignoreIfCacheDirAlreadyIgnoredAtRoot(t *testing.T)
 
 	// Since root .gitignore already has .databricks, there should be no edits
 	// to root .gitignore
-	v, err := NewView(repoPath)
+	v, err := NewView(vfs.MustNew(repoPath))
 	require.NoError(t, err)
 
 	err = v.EnsureValidGitIgnoreExists()
@@ -234,7 +235,7 @@ func TestViewDoesNotChangeGitignoreIfCacheDirAlreadyIgnoredInSubdir(t *testing.T
 
 	// Since root .gitignore already has .databricks, there should be no edits
 	// to a/.gitignore
-	v, err := NewView(filepath.Join(repoPath, "a"))
+	v, err := NewView(vfs.MustNew(filepath.Join(repoPath, "a")))
 	require.NoError(t, err)
 
 	err = v.EnsureValidGitIgnoreExists()
@@ -252,7 +253,7 @@ func TestViewAddsGitignoreWithCacheDir(t *testing.T) {
 	assert.NoError(t, err)
 
 	// Since root .gitignore was deleted, new view adds .databricks to root .gitignore
-	v, err := NewView(repoPath)
+	v, err := NewView(vfs.MustNew(repoPath))
 	require.NoError(t, err)
 
 	err = v.EnsureValidGitIgnoreExists()
@@ -270,7 +271,7 @@ func TestViewAddsGitignoreWithCacheDirAtSubdir(t *testing.T) {
 	require.NoError(t, err)
 
 	// Since root .gitignore was deleted, new view adds .databricks to a/.gitignore
-	v, err := NewView(filepath.Join(repoPath, "a"))
+	v, err := NewView(vfs.MustNew(filepath.Join(repoPath, "a")))
 	require.NoError(t, err)
 
 	err = v.EnsureValidGitIgnoreExists()
@@ -287,7 +288,7 @@ func TestViewAddsGitignoreWithCacheDirAtSubdir(t *testing.T) {
 func TestViewAlwaysIgnoresCacheDir(t *testing.T) {
 	repoPath := createFakeRepo(t, "testdata")
 
-	v, err := NewView(repoPath)
+	v, err := NewView(vfs.MustNew(repoPath))
 	require.NoError(t, err)
 
 	err = v.EnsureValidGitIgnoreExists()
diff --git a/libs/notebook/detect.go b/libs/notebook/detect.go
index 17685f3b..0b7c04d6 100644
--- a/libs/notebook/detect.go
+++ b/libs/notebook/detect.go
@@ -4,6 +4,7 @@ import (
 	"bufio"
 	"bytes"
 	"io"
+	"io/fs"
 	"os"
 	"path/filepath"
 	"strings"
@@ -15,8 +16,8 @@ import (
 const headerLength = 32
 
 // readHeader reads the first N bytes from a file.
-func readHeader(path string) ([]byte, error) {
-	f, err := os.Open(path)
+func readHeader(fsys fs.FS, name string) ([]byte, error) {
+	f, err := fsys.Open(name)
 	if err != nil {
 		return nil, err
 	}
@@ -36,10 +37,10 @@ func readHeader(path string) ([]byte, error) {
 
 // Detect returns whether the file at path is a Databricks notebook.
 // If it is, it returns the notebook language.
-func Detect(path string) (notebook bool, language workspace.Language, err error) {
+func DetectWithFS(fsys fs.FS, name string) (notebook bool, language workspace.Language, err error) {
 	header := ""
 
-	buf, err := readHeader(path)
+	buf, err := readHeader(fsys, name)
 	if err != nil {
 		return false, "", err
 	}
@@ -48,7 +49,7 @@ func Detect(path string) (notebook bool, language workspace.Language, err error)
 	fileHeader := scanner.Text()
 
 	// Determine which header to expect based on filename extension.
-	ext := strings.ToLower(filepath.Ext(path))
+	ext := strings.ToLower(filepath.Ext(name))
 	switch ext {
 	case ".py":
 		header = `# Databricks notebook source`
@@ -63,7 +64,7 @@ func Detect(path string) (notebook bool, language workspace.Language, err error)
 		header = "-- Databricks notebook source"
 		language = workspace.LanguageSql
 	case ".ipynb":
-		return DetectJupyter(path)
+		return DetectJupyterWithFS(fsys, name)
 	default:
 		return false, "", nil
 	}
@@ -74,3 +75,11 @@ func Detect(path string) (notebook bool, language workspace.Language, err error)
 
 	return true, language, nil
 }
+
+// Detect calls DetectWithFS with the local filesystem.
+// The name argument may be a local relative path or a local absolute path.
+func Detect(name string) (notebook bool, language workspace.Language, err error) {
+	d := filepath.ToSlash(filepath.Dir(name))
+	b := filepath.Base(name)
+	return DetectWithFS(os.DirFS(d), b)
+}
diff --git a/libs/notebook/detect_jupyter.go b/libs/notebook/detect_jupyter.go
index 7d96763c..f631b581 100644
--- a/libs/notebook/detect_jupyter.go
+++ b/libs/notebook/detect_jupyter.go
@@ -3,7 +3,9 @@ package notebook
 import (
 	"encoding/json"
 	"fmt"
+	"io/fs"
 	"os"
+	"path/filepath"
 
 	"github.com/databricks/databricks-sdk-go/service/workspace"
 )
@@ -56,8 +58,8 @@ func resolveLanguage(nb *jupyter) workspace.Language {
 // DetectJupyter returns whether the file at path is a valid Jupyter notebook.
 // We assume it is valid if we can read it as JSON and see a couple expected fields.
 // If we cannot, importing into the workspace will always fail, so we also return an error.
-func DetectJupyter(path string) (notebook bool, language workspace.Language, err error) {
-	f, err := os.Open(path)
+func DetectJupyterWithFS(fsys fs.FS, name string) (notebook bool, language workspace.Language, err error) {
+	f, err := fsys.Open(name)
 	if err != nil {
 		return false, "", err
 	}
@@ -68,18 +70,26 @@ func DetectJupyter(path string) (notebook bool, language workspace.Language, err
 	dec := json.NewDecoder(f)
 	err = dec.Decode(&nb)
 	if err != nil {
-		return false, "", fmt.Errorf("%s: error loading Jupyter notebook file: %w", path, err)
+		return false, "", fmt.Errorf("%s: error loading Jupyter notebook file: %w", name, err)
 	}
 
 	// Not a Jupyter notebook if the cells or metadata fields aren't defined.
 	if nb.Cells == nil || nb.Metadata == nil {
-		return false, "", fmt.Errorf("%s: invalid Jupyter notebook file", path)
+		return false, "", fmt.Errorf("%s: invalid Jupyter notebook file", name)
 	}
 
 	// Major version must be at least 4.
 	if nb.NbFormatMajor < 4 {
-		return false, "", fmt.Errorf("%s: unsupported Jupyter notebook version: %d", path, nb.NbFormatMajor)
+		return false, "", fmt.Errorf("%s: unsupported Jupyter notebook version: %d", name, nb.NbFormatMajor)
 	}
 
 	return true, resolveLanguage(&nb), nil
 }
+
+// DetectJupyter calls DetectJupyterWithFS with the local filesystem.
+// The name argument may be a local relative path or a local absolute path.
+func DetectJupyter(name string) (notebook bool, language workspace.Language, err error) {
+	d := filepath.ToSlash(filepath.Dir(name))
+	b := filepath.Base(name)
+	return DetectJupyterWithFS(os.DirFS(d), b)
+}
diff --git a/libs/sync/diff.go b/libs/sync/diff.go
index 074bfc56..e91f7277 100644
--- a/libs/sync/diff.go
+++ b/libs/sync/diff.go
@@ -2,7 +2,6 @@ package sync
 
 import (
 	"path"
-	"path/filepath"
 
 	"golang.org/x/exp/maps"
 )
@@ -64,7 +63,7 @@ func (d *diff) addFilesWithRemoteNameChanged(after *SnapshotState, before *Snaps
 func (d *diff) addNewFiles(after *SnapshotState, before *SnapshotState) {
 	for localName := range after.LastModifiedTimes {
 		if _, ok := before.LastModifiedTimes[localName]; !ok {
-			d.put = append(d.put, filepath.ToSlash(localName))
+			d.put = append(d.put, localName)
 		}
 	}
 
@@ -79,7 +78,7 @@ func (d *diff) addUpdatedFiles(after *SnapshotState, before *SnapshotState) {
 	for localName, modTime := range after.LastModifiedTimes {
 		prevModTime, ok := before.LastModifiedTimes[localName]
 		if ok && modTime.After(prevModTime) {
-			d.put = append(d.put, filepath.ToSlash(localName))
+			d.put = append(d.put, localName)
 		}
 	}
 }
diff --git a/libs/sync/dirset.go b/libs/sync/dirset.go
index 3c37c97c..33b85cb8 100644
--- a/libs/sync/dirset.go
+++ b/libs/sync/dirset.go
@@ -2,7 +2,6 @@ package sync
 
 import (
 	"path"
-	"path/filepath"
 	"sort"
 )
 
@@ -16,8 +15,8 @@ func MakeDirSet(files []string) DirSet {
 
 	// Iterate over all files.
 	for _, f := range files {
-		// Get the directory of the file in /-separated form.
-		dir := filepath.ToSlash(filepath.Dir(f))
+		// Get the directory of the file.
+		dir := path.Dir(f)
 
 		// Add this directory and its parents until it is either "." or already in the set.
 		for dir != "." {
diff --git a/libs/sync/snapshot.go b/libs/sync/snapshot.go
index a27a8c84..392e274d 100644
--- a/libs/sync/snapshot.go
+++ b/libs/sync/snapshot.go
@@ -172,6 +172,11 @@ func loadOrNewSnapshot(ctx context.Context, opts *SyncOptions) (*Snapshot, error
 		return nil, fmt.Errorf("failed to json unmarshal persisted snapshot: %s", err)
 	}
 
+	// Ensure that all paths are slash-separated upon loading
+	// an existing snapshot file. If it was created by an older
+	// CLI version (<= v0.220.0), it may contain backslashes.
+	snapshot.SnapshotState = snapshot.SnapshotState.ToSlash()
+
 	snapshot.New = false
 	return snapshot, nil
 }
diff --git a/libs/sync/snapshot_state.go b/libs/sync/snapshot_state.go
index 10cd34e6..09bb5b63 100644
--- a/libs/sync/snapshot_state.go
+++ b/libs/sync/snapshot_state.go
@@ -2,6 +2,7 @@ package sync
 
 import (
 	"fmt"
+	"path"
 	"path/filepath"
 	"strings"
 	"time"
@@ -48,7 +49,7 @@ func NewSnapshotState(localFiles []fileset.File) (*SnapshotState, error) {
 	for k := range localFiles {
 		f := &localFiles[k]
 		// Compute the remote name the file will have in WSFS
-		remoteName := filepath.ToSlash(f.Relative)
+		remoteName := f.Relative
 		isNotebook, err := f.IsNotebook()
 
 		if err != nil {
@@ -57,7 +58,7 @@ func NewSnapshotState(localFiles []fileset.File) (*SnapshotState, error) {
 			continue
 		}
 		if isNotebook {
-			ext := filepath.Ext(remoteName)
+			ext := path.Ext(remoteName)
 			remoteName = strings.TrimSuffix(remoteName, ext)
 		}
 
@@ -119,3 +120,30 @@ func (fs *SnapshotState) validate() error {
 	}
 	return nil
 }
+
+// ToSlash ensures all local paths in the snapshot state
+// are slash-separated. Returns a new snapshot state.
+func (old SnapshotState) ToSlash() *SnapshotState {
+	new := SnapshotState{
+		LastModifiedTimes:  make(map[string]time.Time),
+		LocalToRemoteNames: make(map[string]string),
+		RemoteToLocalNames: make(map[string]string),
+	}
+
+	// Keys are local paths.
+	for k, v := range old.LastModifiedTimes {
+		new.LastModifiedTimes[filepath.ToSlash(k)] = v
+	}
+
+	// Keys are local paths.
+	for k, v := range old.LocalToRemoteNames {
+		new.LocalToRemoteNames[filepath.ToSlash(k)] = v
+	}
+
+	// Values are remote paths.
+	for k, v := range old.RemoteToLocalNames {
+		new.RemoteToLocalNames[k] = filepath.ToSlash(v)
+	}
+
+	return &new
+}
diff --git a/libs/sync/snapshot_state_test.go b/libs/sync/snapshot_state_test.go
index bfcdbef6..92c14e8e 100644
--- a/libs/sync/snapshot_state_test.go
+++ b/libs/sync/snapshot_state_test.go
@@ -1,25 +1,27 @@
 package sync
 
 import (
+	"runtime"
 	"testing"
 	"time"
 
 	"github.com/databricks/cli/libs/fileset"
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
 
 func TestSnapshotState(t *testing.T) {
-	fileSet := fileset.New("./testdata/sync-fileset")
+	fileSet := fileset.New(vfs.MustNew("./testdata/sync-fileset"))
 	files, err := fileSet.All()
 	require.NoError(t, err)
 
 	// Assert initial contents of the fileset
 	assert.Len(t, files, 4)
-	assert.Equal(t, "invalid-nb.ipynb", files[0].Name())
-	assert.Equal(t, "my-nb.py", files[1].Name())
-	assert.Equal(t, "my-script.py", files[2].Name())
-	assert.Equal(t, "valid-nb.ipynb", files[3].Name())
+	assert.Equal(t, "invalid-nb.ipynb", files[0].Relative)
+	assert.Equal(t, "my-nb.py", files[1].Relative)
+	assert.Equal(t, "my-script.py", files[2].Relative)
+	assert.Equal(t, "valid-nb.ipynb", files[3].Relative)
 
 	// Assert snapshot state generated from the fileset. Note that the invalid notebook
 	// has been ignored.
@@ -114,3 +116,30 @@ func TestSnapshotStateValidationErrors(t *testing.T) {
 	}
 	assert.EqualError(t, s.validate(), "invalid sync state representation. Inconsistent values found. Remote file c points to a. Local file a points to b")
 }
+
+func TestSnapshotStateWithBackslashes(t *testing.T) {
+	if runtime.GOOS != "windows" {
+		t.Skip("Skipping test on non-Windows platform")
+	}
+
+	now := time.Now()
+	s1 := &SnapshotState{
+		LastModifiedTimes: map[string]time.Time{
+			"foo\\bar.py": now,
+		},
+		LocalToRemoteNames: map[string]string{
+			"foo\\bar.py": "foo/bar",
+		},
+		RemoteToLocalNames: map[string]string{
+			"foo/bar": "foo\\bar.py",
+		},
+	}
+
+	assert.NoError(t, s1.validate())
+
+	s2 := s1.ToSlash()
+	assert.NoError(t, s1.validate())
+	assert.Equal(t, map[string]time.Time{"foo/bar.py": now}, s2.LastModifiedTimes)
+	assert.Equal(t, map[string]string{"foo/bar.py": "foo/bar"}, s2.LocalToRemoteNames)
+	assert.Equal(t, map[string]string{"foo/bar": "foo/bar.py"}, s2.RemoteToLocalNames)
+}
diff --git a/libs/sync/snapshot_test.go b/libs/sync/snapshot_test.go
index d6358d4a..050b5d96 100644
--- a/libs/sync/snapshot_test.go
+++ b/libs/sync/snapshot_test.go
@@ -10,6 +10,7 @@ import (
 
 	"github.com/databricks/cli/libs/git"
 	"github.com/databricks/cli/libs/testfile"
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
@@ -29,7 +30,7 @@ func TestDiff(t *testing.T) {
 
 	// Create temp project dir
 	projectDir := t.TempDir()
-	fileSet, err := git.NewFileSet(projectDir)
+	fileSet, err := git.NewFileSet(vfs.MustNew(projectDir))
 	require.NoError(t, err)
 	state := Snapshot{
 		SnapshotState: &SnapshotState{
@@ -93,7 +94,7 @@ func TestSymlinkDiff(t *testing.T) {
 
 	// Create temp project dir
 	projectDir := t.TempDir()
-	fileSet, err := git.NewFileSet(projectDir)
+	fileSet, err := git.NewFileSet(vfs.MustNew(projectDir))
 	require.NoError(t, err)
 	state := Snapshot{
 		SnapshotState: &SnapshotState{
@@ -124,7 +125,7 @@ func TestFolderDiff(t *testing.T) {
 
 	// Create temp project dir
 	projectDir := t.TempDir()
-	fileSet, err := git.NewFileSet(projectDir)
+	fileSet, err := git.NewFileSet(vfs.MustNew(projectDir))
 	require.NoError(t, err)
 	state := Snapshot{
 		SnapshotState: &SnapshotState{
@@ -169,7 +170,7 @@ func TestPythonNotebookDiff(t *testing.T) {
 
 	// Create temp project dir
 	projectDir := t.TempDir()
-	fileSet, err := git.NewFileSet(projectDir)
+	fileSet, err := git.NewFileSet(vfs.MustNew(projectDir))
 	require.NoError(t, err)
 	state := Snapshot{
 		SnapshotState: &SnapshotState{
@@ -244,7 +245,7 @@ func TestErrorWhenIdenticalRemoteName(t *testing.T) {
 
 	// Create temp project dir
 	projectDir := t.TempDir()
-	fileSet, err := git.NewFileSet(projectDir)
+	fileSet, err := git.NewFileSet(vfs.MustNew(projectDir))
 	require.NoError(t, err)
 	state := Snapshot{
 		SnapshotState: &SnapshotState{
@@ -281,7 +282,7 @@ func TestNoErrorRenameWithIdenticalRemoteName(t *testing.T) {
 
 	// Create temp project dir
 	projectDir := t.TempDir()
-	fileSet, err := git.NewFileSet(projectDir)
+	fileSet, err := git.NewFileSet(vfs.MustNew(projectDir))
 	require.NoError(t, err)
 	state := Snapshot{
 		SnapshotState: &SnapshotState{
diff --git a/libs/sync/sync.go b/libs/sync/sync.go
index 30b68ccf..585e8a88 100644
--- a/libs/sync/sync.go
+++ b/libs/sync/sync.go
@@ -10,12 +10,13 @@ import (
 	"github.com/databricks/cli/libs/git"
 	"github.com/databricks/cli/libs/log"
 	"github.com/databricks/cli/libs/set"
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/databricks/databricks-sdk-go"
 	"github.com/databricks/databricks-sdk-go/service/iam"
 )
 
 type SyncOptions struct {
-	LocalPath  string
+	LocalPath  vfs.Path
 	RemotePath string
 	Include    []string
 	Exclude    []string
@@ -54,6 +55,7 @@ func New(ctx context.Context, opts SyncOptions) (*Sync, error) {
 	if err != nil {
 		return nil, err
 	}
+
 	err = fileSet.EnsureValidGitIgnoreExists()
 	if err != nil {
 		return nil, err
@@ -186,7 +188,7 @@ func (s *Sync) GetFileList(ctx context.Context) ([]fileset.File, error) {
 	// tradeoff: doing portable monitoring only due to macOS max descriptor manual ulimit setting requirement
 	// https://github.com/gorakhargosh/watchdog/blob/master/src/watchdog/observers/kqueue.py#L394-L418
 	all := set.NewSetF(func(f fileset.File) string {
-		return f.Absolute
+		return f.Relative
 	})
 	gitFiles, err := s.fileSet.All()
 	if err != nil {
diff --git a/libs/sync/sync_test.go b/libs/sync/sync_test.go
index dc220dbf..292586e8 100644
--- a/libs/sync/sync_test.go
+++ b/libs/sync/sync_test.go
@@ -8,6 +8,7 @@ import (
 
 	"github.com/databricks/cli/libs/fileset"
 	"github.com/databricks/cli/libs/git"
+	"github.com/databricks/cli/libs/vfs"
 	"github.com/stretchr/testify/require"
 )
 
@@ -73,16 +74,17 @@ func TestGetFileSet(t *testing.T) {
 	ctx := context.Background()
 
 	dir := setupFiles(t)
-	fileSet, err := git.NewFileSet(dir)
+	root := vfs.MustNew(dir)
+	fileSet, err := git.NewFileSet(root)
 	require.NoError(t, err)
 
 	err = fileSet.EnsureValidGitIgnoreExists()
 	require.NoError(t, err)
 
-	inc, err := fileset.NewGlobSet(dir, []string{})
+	inc, err := fileset.NewGlobSet(root, []string{})
 	require.NoError(t, err)
 
-	excl, err := fileset.NewGlobSet(dir, []string{})
+	excl, err := fileset.NewGlobSet(root, []string{})
 	require.NoError(t, err)
 
 	s := &Sync{
@@ -97,10 +99,10 @@ func TestGetFileSet(t *testing.T) {
 	require.NoError(t, err)
 	require.Equal(t, len(fileList), 9)
 
-	inc, err = fileset.NewGlobSet(dir, []string{})
+	inc, err = fileset.NewGlobSet(root, []string{})
 	require.NoError(t, err)
 
-	excl, err = fileset.NewGlobSet(dir, []string{"*.go"})
+	excl, err = fileset.NewGlobSet(root, []string{"*.go"})
 	require.NoError(t, err)
 
 	s = &Sync{
@@ -115,10 +117,10 @@ func TestGetFileSet(t *testing.T) {
 	require.NoError(t, err)
 	require.Equal(t, len(fileList), 1)
 
-	inc, err = fileset.NewGlobSet(dir, []string{".databricks/*"})
+	inc, err = fileset.NewGlobSet(root, []string{".databricks/*"})
 	require.NoError(t, err)
 
-	excl, err = fileset.NewGlobSet(dir, []string{})
+	excl, err = fileset.NewGlobSet(root, []string{})
 	require.NoError(t, err)
 
 	s = &Sync{
@@ -138,16 +140,17 @@ func TestRecursiveExclude(t *testing.T) {
 	ctx := context.Background()
 
 	dir := setupFiles(t)
-	fileSet, err := git.NewFileSet(dir)
+	root := vfs.MustNew(dir)
+	fileSet, err := git.NewFileSet(root)
 	require.NoError(t, err)
 
 	err = fileSet.EnsureValidGitIgnoreExists()
 	require.NoError(t, err)
 
-	inc, err := fileset.NewGlobSet(dir, []string{})
+	inc, err := fileset.NewGlobSet(root, []string{})
 	require.NoError(t, err)
 
-	excl, err := fileset.NewGlobSet(dir, []string{"test/**"})
+	excl, err := fileset.NewGlobSet(root, []string{"test/**"})
 	require.NoError(t, err)
 
 	s := &Sync{
diff --git a/libs/sync/watchdog.go b/libs/sync/watchdog.go
index b0c96e01..ca7ec46e 100644
--- a/libs/sync/watchdog.go
+++ b/libs/sync/watchdog.go
@@ -4,8 +4,6 @@ import (
 	"context"
 	"errors"
 	"io/fs"
-	"os"
-	"path/filepath"
 
 	"github.com/databricks/cli/libs/filer"
 	"github.com/databricks/cli/libs/log"
@@ -59,7 +57,7 @@ func (s *Sync) applyMkdir(ctx context.Context, localName string) error {
 func (s *Sync) applyPut(ctx context.Context, localName string) error {
 	s.notifyProgress(ctx, EventActionPut, localName, 0.0)
 
-	localFile, err := os.Open(filepath.Join(s.LocalPath, localName))
+	localFile, err := s.LocalPath.Open(localName)
 	if err != nil {
 		return err
 	}
diff --git a/libs/vfs/leaf.go b/libs/vfs/leaf.go
new file mode 100644
index 00000000..8c11f903
--- /dev/null
+++ b/libs/vfs/leaf.go
@@ -0,0 +1,29 @@
+package vfs
+
+import (
+	"errors"
+	"io/fs"
+)
+
+// FindLeafInTree returns the first path that holds `name`,
+// traversing up to the root of the filesystem, starting at `p`.
+func FindLeafInTree(p Path, name string) (Path, error) {
+	for p != nil {
+		_, err := fs.Stat(p, name)
+
+		// No error means we found the leaf in p.
+		if err == nil {
+			return p, nil
+		}
+
+		// ErrNotExist means we continue traversal up the tree.
+		if errors.Is(err, fs.ErrNotExist) {
+			p = p.Parent()
+			continue
+		}
+
+		return nil, err
+	}
+
+	return nil, fs.ErrNotExist
+}
diff --git a/libs/vfs/leaf_test.go b/libs/vfs/leaf_test.go
new file mode 100644
index 00000000..da9412ec
--- /dev/null
+++ b/libs/vfs/leaf_test.go
@@ -0,0 +1,38 @@
+package vfs
+
+import (
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestFindLeafInTree(t *testing.T) {
+	wd, err := os.Getwd()
+	require.NoError(t, err)
+
+	root := filepath.Join(wd, "..", "..")
+
+	// Find from working directory should work.
+	{
+		out, err := FindLeafInTree(MustNew(wd), ".git")
+		assert.NoError(t, err)
+		assert.Equal(t, root, out.Native())
+	}
+
+	// Find from project root itself should work.
+	{
+		out, err := FindLeafInTree(MustNew(root), ".git")
+		assert.NoError(t, err)
+		assert.Equal(t, root, out.Native())
+	}
+
+	// Find for something that doesn't exist should work.
+	{
+		out, err := FindLeafInTree(MustNew(root), "this-leaf-doesnt-exist-anywhere")
+		assert.ErrorIs(t, err, os.ErrNotExist)
+		assert.Equal(t, nil, out)
+	}
+}
diff --git a/libs/vfs/os.go b/libs/vfs/os.go
new file mode 100644
index 00000000..26447d83
--- /dev/null
+++ b/libs/vfs/os.go
@@ -0,0 +1,82 @@
+package vfs
+
+import (
+	"io/fs"
+	"os"
+	"path/filepath"
+)
+
+type osPath struct {
+	path string
+
+	openFn     func(name string) (fs.File, error)
+	statFn     func(name string) (fs.FileInfo, error)
+	readDirFn  func(name string) ([]fs.DirEntry, error)
+	readFileFn func(name string) ([]byte, error)
+}
+
+func New(name string) (Path, error) {
+	abs, err := filepath.Abs(name)
+	if err != nil {
+		return nil, err
+	}
+
+	return newOsPath(abs), nil
+}
+
+func MustNew(name string) Path {
+	p, err := New(name)
+	if err != nil {
+		panic(err)
+	}
+
+	return p
+}
+
+func newOsPath(name string) Path {
+	if !filepath.IsAbs(name) {
+		panic("vfs: abs path must be absolute")
+	}
+
+	// [os.DirFS] implements all required interfaces.
+	// We used type assertion below to get the underlying types.
+	dirfs := os.DirFS(name)
+
+	return &osPath{
+		path: name,
+
+		openFn:     dirfs.Open,
+		statFn:     dirfs.(fs.StatFS).Stat,
+		readDirFn:  dirfs.(fs.ReadDirFS).ReadDir,
+		readFileFn: dirfs.(fs.ReadFileFS).ReadFile,
+	}
+}
+
+func (o osPath) Open(name string) (fs.File, error) {
+	return o.openFn(name)
+}
+
+func (o osPath) Stat(name string) (fs.FileInfo, error) {
+	return o.statFn(name)
+}
+
+func (o osPath) ReadDir(name string) ([]fs.DirEntry, error) {
+	return o.readDirFn(name)
+}
+
+func (o osPath) ReadFile(name string) ([]byte, error) {
+	return o.readFileFn(name)
+}
+
+func (o osPath) Parent() Path {
+	dir := filepath.Dir(o.path)
+	if dir == o.path {
+		return nil
+	}
+
+	return newOsPath(dir)
+}
+
+func (o osPath) Native() string {
+	return o.path
+}
diff --git a/libs/vfs/os_test.go b/libs/vfs/os_test.go
new file mode 100644
index 00000000..6199bdc7
--- /dev/null
+++ b/libs/vfs/os_test.go
@@ -0,0 +1,54 @@
+package vfs
+
+import (
+	"os"
+	"path/filepath"
+	"runtime"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestOsNewWithRelativePath(t *testing.T) {
+	wd, err := os.Getwd()
+	require.NoError(t, err)
+
+	p, err := New(".")
+	require.NoError(t, err)
+	require.Equal(t, wd, p.Native())
+}
+
+func TestOsPathParent(t *testing.T) {
+	wd, err := os.Getwd()
+	require.NoError(t, err)
+
+	p := MustNew(wd)
+	require.NotNil(t, p)
+
+	// Traverse all the way to the root.
+	for {
+		q := p.Parent()
+		if q == nil {
+			// Parent returns nil when it is the root.
+			break
+		}
+
+		p = q
+	}
+
+	// We should have reached the root.
+	if runtime.GOOS == "windows" {
+		require.Equal(t, filepath.VolumeName(wd)+`\`, p.Native())
+	} else {
+		require.Equal(t, "/", p.Native())
+	}
+}
+
+func TestOsPathNative(t *testing.T) {
+	wd, err := os.Getwd()
+	require.NoError(t, err)
+
+	p := MustNew(wd)
+	require.NotNil(t, p)
+	require.Equal(t, wd, p.Native())
+}
diff --git a/libs/vfs/path.go b/libs/vfs/path.go
new file mode 100644
index 00000000..19f119d5
--- /dev/null
+++ b/libs/vfs/path.go
@@ -0,0 +1,29 @@
+package vfs
+
+import "io/fs"
+
+// FS combines the fs.FS, fs.StatFS, fs.ReadDirFS, and fs.ReadFileFS interfaces.
+// It mandates that Path implementations must support all these interfaces.
+type FS interface {
+	fs.FS
+	fs.StatFS
+	fs.ReadDirFS
+	fs.ReadFileFS
+}
+
+// Path defines a read-only virtual file system interface for:
+//
+// 1. Intercepting file operations to inject custom logic (e.g., logging, access control).
+// 2. Traversing directories to find specific leaf directories (e.g., .git).
+// 3. Converting virtual paths to OS-native paths.
+//
+// Options 2 and 3 are not possible with the standard fs.FS interface.
+// They are needed such that we can provide an instance to the sync package
+// and still detect the containing .git directory and convert paths to native paths.
+type Path interface {
+	FS
+
+	Parent() Path
+
+	Native() string
+}
diff --git a/libs/vfs/path_test.go b/libs/vfs/path_test.go
new file mode 100644
index 00000000..54c60940
--- /dev/null
+++ b/libs/vfs/path_test.go
@@ -0,0 +1 @@
+package vfs