diff --git a/bundle/config/mutator/translate_paths.go b/bundle/config/mutator/translate_paths.go
index a2c830be36..1eda578fae 100644
--- a/bundle/config/mutator/translate_paths.go
+++ b/bundle/config/mutator/translate_paths.go
@@ -136,7 +136,7 @@ func (t *translateContext) rewritePath(
 	}
 
 	// Local path is relative to the directory the resource was defined in.
-	localPath := filepath.Join(dir, filepath.FromSlash(input))
+	localPath := filepath.Join(dir, input)
 	if interp, ok := t.seen[localPath]; ok {
 		return interp, nil
 	}
@@ -151,6 +151,10 @@ func (t *translateContext) rewritePath(
 		return "", fmt.Errorf("path %s is not contained in sync root path", localPath)
 	}
 
+	// Normalize paths to separated by forward slashes.
+	localPath = filepath.ToSlash(localPath)
+	localRelPath = filepath.ToSlash(localRelPath)
+
 	// Convert local path into workspace path via specified function.
 	var interp string
 	switch opts.Mode {
@@ -180,9 +184,9 @@ func (t *translateContext) rewritePath(
 }
 
 func (t *translateContext) translateNotebookPath(ctx context.Context, literal, localFullPath, localRelPath string) (string, error) {
-	nb, _, err := notebook.DetectWithFS(t.b.SyncRoot, filepath.ToSlash(localRelPath))
+	nb, _, err := notebook.DetectWithFS(t.b.SyncRoot, localRelPath)
 	if errors.Is(err, fs.ErrNotExist) {
-		if filepath.Ext(localFullPath) != notebook.ExtensionNone {
+		if path.Ext(localFullPath) != notebook.ExtensionNone {
 			return "", fmt.Errorf("notebook %s not found", literal)
 		}
 
@@ -198,7 +202,7 @@ func (t *translateContext) translateNotebookPath(ctx context.Context, literal, l
 		// way we can provide a more targeted error message.
 		for _, ext := range extensions {
 			literalWithExt := literal + ext
-			localRelPathWithExt := filepath.ToSlash(localRelPath + ext)
+			localRelPathWithExt := localRelPath + ext
 			if _, err := fs.Stat(t.b.SyncRoot, localRelPathWithExt); err == nil {
 				return "", fmt.Errorf(`notebook %s not found. Did you mean %s?
 Local notebook references are expected to contain one of the following
@@ -218,42 +222,42 @@ to contain one of the following file extensions: [%s]`, literal, strings.Join(ex
 	}
 
 	// Upon import, notebooks are stripped of their extension.
-	localRelPathNoExt := strings.TrimSuffix(localRelPath, filepath.Ext(localRelPath))
-	return path.Join(t.remoteRoot, filepath.ToSlash(localRelPathNoExt)), nil
+	localRelPathNoExt := strings.TrimSuffix(localRelPath, path.Ext(localRelPath))
+	return path.Join(t.remoteRoot, localRelPathNoExt), nil
 }
 
 func (t *translateContext) translateFilePath(ctx context.Context, literal, localFullPath, localRelPath string) (string, error) {
-	nb, _, err := notebook.DetectWithFS(t.b.SyncRoot, filepath.ToSlash(localRelPath))
+	nb, _, err := notebook.DetectWithFS(t.b.SyncRoot, localRelPath)
 	if errors.Is(err, fs.ErrNotExist) {
 		return "", fmt.Errorf("file %s not found", literal)
 	}
 	if err != nil {
-		return "", fmt.Errorf("unable to determine if %s is not a notebook: %w", localFullPath, err)
+		return "", fmt.Errorf("unable to determine if %s is not a notebook: %w", filepath.FromSlash(localFullPath), err)
 	}
 	if nb {
 		return "", ErrIsNotebook{localFullPath}
 	}
-	return path.Join(t.remoteRoot, filepath.ToSlash(localRelPath)), nil
+	return path.Join(t.remoteRoot, localRelPath), nil
 }
 
 func (t *translateContext) translateDirectoryPath(ctx context.Context, literal, localFullPath, localRelPath string) (string, error) {
-	info, err := t.b.SyncRoot.Stat(filepath.ToSlash(localRelPath))
+	info, err := t.b.SyncRoot.Stat(localRelPath)
 	if err != nil {
 		return "", err
 	}
 	if !info.IsDir() {
-		return "", fmt.Errorf("%s is not a directory", localFullPath)
+		return "", fmt.Errorf("%s is not a directory", filepath.FromSlash(localFullPath))
 	}
-	return path.Join(t.remoteRoot, filepath.ToSlash(localRelPath)), nil
+	return path.Join(t.remoteRoot, localRelPath), nil
 }
 
 func (t *translateContext) translateLocalAbsoluteFilePath(ctx context.Context, literal, localFullPath, localRelPath string) (string, error) {
-	info, err := t.b.SyncRoot.Stat(filepath.ToSlash(localRelPath))
+	info, err := t.b.SyncRoot.Stat(localRelPath)
 	if errors.Is(err, fs.ErrNotExist) {
 		return "", fmt.Errorf("file %s not found", literal)
 	}
 	if err != nil {
-		return "", fmt.Errorf("unable to determine if %s is a file: %w", localFullPath, err)
+		return "", fmt.Errorf("unable to determine if %s is a file: %w", filepath.FromSlash(localFullPath), err)
 	}
 	if info.IsDir() {
 		return "", fmt.Errorf("expected %s to be a file but found a directory", literal)
@@ -262,12 +266,12 @@ func (t *translateContext) translateLocalAbsoluteFilePath(ctx context.Context, l
 }
 
 func (t *translateContext) translateLocalAbsoluteDirectoryPath(ctx context.Context, literal, localFullPath, _ string) (string, error) {
-	info, err := os.Stat(localFullPath)
+	info, err := os.Stat(filepath.FromSlash(localFullPath))
 	if errors.Is(err, fs.ErrNotExist) {
 		return "", fmt.Errorf("directory %s not found", literal)
 	}
 	if err != nil {
-		return "", fmt.Errorf("unable to determine if %s is a directory: %w", localFullPath, err)
+		return "", fmt.Errorf("unable to determine if %s is a directory: %w", filepath.FromSlash(localFullPath), err)
 	}
 	if !info.IsDir() {
 		return "", fmt.Errorf("expected %s to be a directory but found a file", literal)
@@ -281,7 +285,7 @@ func (t *translateContext) translateLocalRelativePath(ctx context.Context, liter
 
 func (t *translateContext) translateLocalRelativeWithPrefixPath(ctx context.Context, literal, localFullPath, localRelPath string) (string, error) {
 	if !strings.HasPrefix(localRelPath, ".") {
-		localRelPath = "." + string(filepath.Separator) + localRelPath
+		localRelPath = "./" + localRelPath
 	}
 	return localRelPath, nil
 }
diff --git a/bundle/config/mutator/translate_paths_artifacts_test.go b/bundle/config/mutator/translate_paths_artifacts_test.go
index fb402b488e..0d1af61569 100644
--- a/bundle/config/mutator/translate_paths_artifacts_test.go
+++ b/bundle/config/mutator/translate_paths_artifacts_test.go
@@ -46,7 +46,7 @@ func TestTranslatePathsArtifacts_InsideSyncRoot(t *testing.T) {
 	require.NoError(t, diags.Error())
 
 	// Assert that the artifact path has been converted to a local absolute path.
-	assert.Equal(t, lib, b.Config.Artifacts["my_artifact"].Path)
+	assert.Equal(t, filepath.ToSlash(lib), b.Config.Artifacts["my_artifact"].Path)
 }
 
 func TestTranslatePathsArtifacts_OutsideSyncRoot(t *testing.T) {
@@ -79,5 +79,5 @@ func TestTranslatePathsArtifacts_OutsideSyncRoot(t *testing.T) {
 	require.NoError(t, diags.Error())
 
 	// Assert that the artifact path has been converted to a local absolute path.
-	assert.Equal(t, lib, b.Config.Artifacts["my_artifact"].Path)
+	assert.Equal(t, filepath.ToSlash(lib), b.Config.Artifacts["my_artifact"].Path)
 }
diff --git a/bundle/config/mutator/translate_paths_dashboards_test.go b/bundle/config/mutator/translate_paths_dashboards_test.go
index 5e4e69f5d8..02fba92e0a 100644
--- a/bundle/config/mutator/translate_paths_dashboards_test.go
+++ b/bundle/config/mutator/translate_paths_dashboards_test.go
@@ -48,7 +48,7 @@ func TestTranslatePathsDashboards_FilePathRelativeSubDirectory(t *testing.T) {
 	// Assert that the file path for the dashboard has been converted to its local absolute path.
 	assert.Equal(
 		t,
-		filepath.Join(dir, "src", "my_dashboard.lvdash.json"),
+		filepath.ToSlash(filepath.Join(dir, "src", "my_dashboard.lvdash.json")),
 		b.Config.Resources.Dashboards["dashboard"].FilePath,
 	)
 }
diff --git a/bundle/config/mutator/translate_paths_test.go b/bundle/config/mutator/translate_paths_test.go
index 493abb8c5f..aa6488ab09 100644
--- a/bundle/config/mutator/translate_paths_test.go
+++ b/bundle/config/mutator/translate_paths_test.go
@@ -6,7 +6,6 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
-	"strings"
 	"testing"
 
 	"github.com/databricks/cli/bundle"
@@ -226,7 +225,7 @@ func TestTranslatePaths(t *testing.T) {
 	)
 	assert.Equal(
 		t,
-		filepath.Join("dist", "task.whl"),
+		"dist/task.whl",
 		b.Config.Resources.Jobs["job"].Tasks[0].Libraries[0].Whl,
 	)
 	assert.Equal(
@@ -251,7 +250,7 @@ func TestTranslatePaths(t *testing.T) {
 	)
 	assert.Equal(
 		t,
-		filepath.Join("dist", "task.jar"),
+		"dist/task.jar",
 		b.Config.Resources.Jobs["job"].Tasks[5].Libraries[0].Jar,
 	)
 	assert.Equal(
@@ -362,7 +361,7 @@ func TestTranslatePathsInSubdirectories(t *testing.T) {
 	)
 	assert.Equal(
 		t,
-		filepath.Join("job", "dist", "task.jar"),
+		"job/dist/task.jar",
 		b.Config.Resources.Jobs["job"].Tasks[1].Libraries[0].Jar,
 	)
 	assert.Equal(
@@ -774,8 +773,8 @@ func TestTranslatePathJobEnvironments(t *testing.T) {
 	diags := bundle.Apply(context.Background(), b, mutator.TranslatePaths())
 	require.NoError(t, diags.Error())
 
-	assert.Equal(t, strings.Join([]string{".", "job", "dist", "env1.whl"}, string(os.PathSeparator)), b.Config.Resources.Jobs["job"].JobSettings.Environments[0].Spec.Dependencies[0])
-	assert.Equal(t, strings.Join([]string{".", "dist", "env2.whl"}, string(os.PathSeparator)), b.Config.Resources.Jobs["job"].JobSettings.Environments[0].Spec.Dependencies[1])
+	assert.Equal(t, "./job/dist/env1.whl", b.Config.Resources.Jobs["job"].JobSettings.Environments[0].Spec.Dependencies[0])
+	assert.Equal(t, "./dist/env2.whl", b.Config.Resources.Jobs["job"].JobSettings.Environments[0].Spec.Dependencies[1])
 	assert.Equal(t, "simplejson", b.Config.Resources.Jobs["job"].JobSettings.Environments[0].Spec.Dependencies[2])
 	assert.Equal(t, "/Workspace/Users/foo@bar.com/test.whl", b.Config.Resources.Jobs["job"].JobSettings.Environments[0].Spec.Dependencies[3])
 	assert.Equal(t, "--extra-index-url https://name:token@gitlab.com/api/v4/projects/9876/packages/pypi/simple foobar", b.Config.Resources.Jobs["job"].JobSettings.Environments[0].Spec.Dependencies[4])
@@ -839,7 +838,7 @@ func TestTranslatePathWithComplexVariables(t *testing.T) {
 
 	assert.Equal(
 		t,
-		filepath.Join("variables", "local", "whl.whl"),
+		"variables/local/whl.whl",
 		b.Config.Resources.Jobs["job"].Tasks[0].Libraries[0].Whl,
 	)
 }
@@ -952,34 +951,34 @@ func TestTranslatePathsWithSourceLinkedDeployment(t *testing.T) {
 	// updated to source path
 	assert.Equal(
 		t,
-		filepath.Join(dir, "my_job_notebook"),
+		dir+"/my_job_notebook",
 		b.Config.Resources.Jobs["job"].Tasks[0].NotebookTask.NotebookPath,
 	)
 	assert.Equal(
 		t,
-		filepath.Join(dir, "requirements.txt"),
+		dir+"/requirements.txt",
 		b.Config.Resources.Jobs["job"].Tasks[2].Libraries[0].Requirements,
 	)
 	assert.Equal(
 		t,
-		filepath.Join(dir, "my_python_file.py"),
+		dir+"/my_python_file.py",
 		b.Config.Resources.Jobs["job"].Tasks[3].SparkPythonTask.PythonFile,
 	)
 	assert.Equal(
 		t,
-		filepath.Join(dir, "my_pipeline_notebook"),
+		dir+"/my_pipeline_notebook",
 		b.Config.Resources.Pipelines["pipeline"].Libraries[0].Notebook.Path,
 	)
 	assert.Equal(
 		t,
-		filepath.Join(dir, "my_python_file.py"),
+		dir+"/my_python_file.py",
 		b.Config.Resources.Pipelines["pipeline"].Libraries[2].File.Path,
 	)
 
 	// left as is
 	assert.Equal(
 		t,
-		filepath.Join("dist", "task.whl"),
+		"dist/task.whl",
 		b.Config.Resources.Jobs["job"].Tasks[0].Libraries[0].Whl,
 	)
 	assert.Equal(
@@ -989,7 +988,7 @@ func TestTranslatePathsWithSourceLinkedDeployment(t *testing.T) {
 	)
 	assert.Equal(
 		t,
-		filepath.Join("dist", "task.jar"),
+		"dist/task.jar",
 		b.Config.Resources.Jobs["job"].Tasks[4].Libraries[0].Jar,
 	)
 	assert.Equal(
diff --git a/bundle/tests/relative_path_with_includes_test.go b/bundle/tests/relative_path_with_includes_test.go
index 8efac00394..7249cac1f7 100644
--- a/bundle/tests/relative_path_with_includes_test.go
+++ b/bundle/tests/relative_path_with_includes_test.go
@@ -17,8 +17,8 @@ func TestRelativePathsWithIncludes(t *testing.T) {
 	diags := bundle.Apply(context.Background(), b, m)
 	assert.NoError(t, diags.Error())
 
-	assert.Equal(t, filepath.Join(b.SyncRootPath, "artifact_a"), b.Config.Artifacts["test_a"].Path)
-	assert.Equal(t, filepath.Join(b.SyncRootPath, "subfolder", "artifact_b"), b.Config.Artifacts["test_b"].Path)
+	assert.Equal(t, b.SyncRootPath+"/artifact_a", b.Config.Artifacts["test_a"].Path)
+	assert.Equal(t, b.SyncRootPath+"/subfolder/artifact_b", b.Config.Artifacts["test_b"].Path)
 
 	assert.ElementsMatch(
 		t,
@@ -37,6 +37,6 @@ func TestRelativePathsWithIncludes(t *testing.T) {
 		b.Config.Sync.Exclude,
 	)
 
-	assert.Equal(t, filepath.Join("dist", "job_a.whl"), b.Config.Resources.Jobs["job_a"].Tasks[0].Libraries[0].Whl)
-	assert.Equal(t, filepath.Join("subfolder", "dist", "job_b.whl"), b.Config.Resources.Jobs["job_b"].Tasks[0].Libraries[0].Whl)
+	assert.Equal(t, "dist/job_a.whl", b.Config.Resources.Jobs["job_a"].Tasks[0].Libraries[0].Whl)
+	assert.Equal(t, "subfolder/dist/job_b.whl", b.Config.Resources.Jobs["job_b"].Tasks[0].Libraries[0].Whl)
 }