diff --git a/acceptance/bundle/config-remote-sync/validation_errors/databricks.yml.tmpl b/acceptance/bundle/config-remote-sync/validation_errors/databricks.yml.tmpl
new file mode 100644
index 0000000000..c63034835c
--- /dev/null
+++ b/acceptance/bundle/config-remote-sync/validation_errors/databricks.yml.tmpl
@@ -0,0 +1,26 @@
+bundle:
+  name: test-bundle-$UNIQUE_NAME
+
+resources:
+  pipelines:
+    my_pipeline:
+      name: test-pipeline-$UNIQUE_NAME
+      root_path: ./pipeline_root
+      libraries:
+        - notebook:
+            path: /Users/{{workspace_user_name}}/notebook
+
+  jobs:
+    my_job:
+      tasks:
+        - task_key: main
+          notebook_task:
+            notebook_path: ./src/notebook.py
+          new_cluster:
+            spark_version: $DEFAULT_SPARK_VERSION
+            node_type_id: $NODE_TYPE_ID
+            num_workers: 1
+
+targets:
+  default:
+    mode: development
diff --git a/acceptance/bundle/config-remote-sync/validation_errors/out.test.toml b/acceptance/bundle/config-remote-sync/validation_errors/out.test.toml
new file mode 100644
index 0000000000..c4500f378d
--- /dev/null
+++ b/acceptance/bundle/config-remote-sync/validation_errors/out.test.toml
@@ -0,0 +1,8 @@
+Local = true
+Cloud = false
+
+[GOOS]
+  windows = false
+
+[EnvMatrix]
+  DATABRICKS_BUNDLE_ENGINE = ["direct", "terraform"]
diff --git a/acceptance/bundle/config-remote-sync/validation_errors/output.txt b/acceptance/bundle/config-remote-sync/validation_errors/output.txt
new file mode 100644
index 0000000000..c4ce29efa0
--- /dev/null
+++ b/acceptance/bundle/config-remote-sync/validation_errors/output.txt
@@ -0,0 +1,60 @@
+Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/test-bundle-[UNIQUE_NAME]/default/files...
+Deploying resources...
+Updating deployment state...
+Deployment complete!
+
+=== Set correct paths and add git info remotely
+=== Break local paths to simulate stale config
+=== Sync with broken local paths
+Detected changes in 2 resource(s):
+
+Resource: resources.jobs.my_job
+  git_source: add
+  tasks[task_key='main'].notebook_task.notebook_path: replace
+
+Resource: resources.pipelines.my_pipeline
+  root_path: replace
+
+
+
+=== Configuration changes
+
+>>> diff.py databricks.yml.backup databricks.yml
+--- databricks.yml.backup
++++ databricks.yml
+@@ -6,5 +6,5 @@
+     my_pipeline:
+       name: test-pipeline-[UNIQUE_NAME]
+-      root_path: ./pipeline_root
++      root_path: ./pipeline_root_v2
+       libraries:
+         - notebook:
+@@ -16,9 +16,13 @@
+         - task_key: main
+           notebook_task:
+-            notebook_path: ./src/notebook.py
++            notebook_path: /Users/[USERNAME]/notebook
+           new_cluster:
+             spark_version: 13.3.x-snapshot-scala2.12
+             node_type_id: [NODE_TYPE_ID]
+             num_workers: 1
++      git_source:
++        git_branch: main
++        git_provider: gitHub
++        git_url: https://github.com/databricks/databricks-sdk-go.git
+
+ targets:
+
+>>> [CLI] bundle destroy --auto-approve
+The following resources will be deleted:
+  delete resources.jobs.my_job
+  delete resources.pipelines.my_pipeline
+
+This action will result in the deletion of the following Lakeflow Spark Declarative Pipelines along with the
+Streaming Tables (STs) and Materialized Views (MVs) managed by them:
+  delete resources.pipelines.my_pipeline
+
+All files and directories at the following location will be deleted: /Workspace/Users/[USERNAME]/.bundle/test-bundle-[UNIQUE_NAME]/default
+
+Deleting files...
+Destroy complete!
diff --git a/acceptance/bundle/config-remote-sync/validation_errors/script b/acceptance/bundle/config-remote-sync/validation_errors/script
new file mode 100644
index 0000000000..828ec20644
--- /dev/null
+++ b/acceptance/bundle/config-remote-sync/validation_errors/script
@@ -0,0 +1,48 @@
+envsubst < databricks.yml.tmpl > databricks.yml
+
+# Create valid paths so that initial deploy succeeds
+mkdir -p pipeline_root src
+echo '# Databricks notebook source' > src/notebook.py
+
+cleanup() {
+  # Restore valid paths for destroy to work (includes pipeline_root_v2 from sync)
+  mkdir -p pipeline_root pipeline_root_v2 src
+  echo '# Databricks notebook source' > src/notebook.py
+  trace $CLI bundle destroy --auto-approve
+}
+trap cleanup EXIT
+
+$CLI bundle deploy
+job_id="$(read_id.py my_job)"
+pipeline_id="$(read_id.py my_pipeline)"
+
+
+title "Set correct paths and add git info remotely"
+edit_resource.py pipelines $pipeline_id <<EOF
+r["root_path"] = "${PWD}/pipeline_root_v2"
+EOF
+
+edit_resource.py jobs $job_id <<EOF
+r["tasks"][0]["notebook_task"]["notebook_path"] = "/Users/${CURRENT_USER_NAME}/notebook"
+r["git_source"] = {
+    "git_url": "https://github.com/databricks/databricks-sdk-go.git",
+    "git_branch": "main",
+    "git_provider": "gitHub"
+}
+EOF
+
+
+title "Break local paths to simulate stale config"
+# Remove the directories so the config now references non-existent relative paths
+rm -rf pipeline_root src
+
+
+title "Sync with broken local paths"
+echo
+cp databricks.yml databricks.yml.backup
+$CLI bundle config-remote-sync --save
+
+title "Configuration changes"
+echo
+trace diff.py databricks.yml.backup databricks.yml
+rm databricks.yml.backup
diff --git a/acceptance/bundle/config-remote-sync/validation_errors/test.toml b/acceptance/bundle/config-remote-sync/validation_errors/test.toml
new file mode 100644
index 0000000000..ff9cea4cfc
--- /dev/null
+++ b/acceptance/bundle/config-remote-sync/validation_errors/test.toml
@@ -0,0 +1,8 @@
+RecordRequests = false
+Ignore = [".databricks", "databricks.yml", "databricks.yml.backup", "src", "pipeline_root"]
+
+[Env]
+DATABRICKS_BUNDLE_ENABLE_EXPERIMENTAL_YAML_SYNC = "true"
+
+[EnvMatrix]
+DATABRICKS_BUNDLE_ENGINE = ["direct", "terraform"]
diff --git a/bundle/bundle.go b/bundle/bundle.go
index b2dae07554..588c573ca4 100644
--- a/bundle/bundle.go
+++ b/bundle/bundle.go
@@ -149,6 +149,11 @@ type Bundle struct {
 	// files
 	AutoApprove bool
 
+	// SkipLocalFileValidation makes path translation tolerant of missing local files.
+	// When set, TranslatePaths computes workspace paths without verifying files exist.
+	// Used by config-remote-sync which may run when referenced local files are stale.
+	SkipLocalFileValidation bool
+
 	// Tagging is used to normalize tag keys and values.
 	// The implementation depends on the cloud being targeted.
 	Tagging tags.Cloud
diff --git a/bundle/config/mutator/translate_paths.go b/bundle/config/mutator/translate_paths.go
index 213bf37fad..8b72f6942a 100644
--- a/bundle/config/mutator/translate_paths.go
+++ b/bundle/config/mutator/translate_paths.go
@@ -84,6 +84,10 @@ type translateContext struct {
 	// It is equal to ${workspace.file_path} for regular deployments.
 	// It points to the source root path for source-linked deployments.
 	remoteRoot string
+
+	// skipLocalFileValidation makes path translation tolerant of missing local files.
+	// When set, paths are translated without verifying files exist on the local filesystem.
+	skipLocalFileValidation bool
 }
 
 // rewritePath converts a given relative path from the loaded config to a new path based on the passed rewriting function
@@ -180,6 +184,11 @@ func (t *translateContext) rewritePath(
 func (t *translateContext) translateNotebookPath(ctx context.Context, literal, localFullPath, localRelPath string) (string, error) {
 	nb, _, err := notebook.DetectWithFS(t.b.SyncRoot, localRelPath)
 	if errors.Is(err, fs.ErrNotExist) {
+		if t.skipLocalFileValidation {
+			localRelPathNoExt := strings.TrimSuffix(localRelPath, path.Ext(localRelPath))
+			return path.Join(t.remoteRoot, localRelPathNoExt), nil
+		}
+
 		if path.Ext(localFullPath) != notebook.ExtensionNone {
 			return "", fmt.Errorf("notebook %s not found", literal)
 		}
@@ -215,6 +224,9 @@ to contain one of the following file extensions: [%s]`, literal, strings.Join(no
 func (t *translateContext) translateFilePath(ctx context.Context, literal, localFullPath, localRelPath string) (string, error) {
 	nb, _, err := notebook.DetectWithFS(t.b.SyncRoot, localRelPath)
 	if errors.Is(err, fs.ErrNotExist) {
+		if t.skipLocalFileValidation {
+			return path.Join(t.remoteRoot, localRelPath), nil
+		}
 		return "", fmt.Errorf("file %s not found", literal)
 	}
 	if err != nil {
@@ -229,6 +241,9 @@ func (t *translateContext) translateFilePath(ctx context.Context, literal, local
 func (t *translateContext) translateDirectoryPath(ctx context.Context, literal, localFullPath, localRelPath string) (string, error) {
 	info, err := t.b.SyncRoot.Stat(localRelPath)
 	if err != nil {
+		if t.skipLocalFileValidation {
+			return path.Join(t.remoteRoot, localRelPath), nil
+		}
 		return "", err
 	}
 	if !info.IsDir() {
@@ -244,6 +259,9 @@ func (t *translateContext) translateGlobPath(ctx context.Context, literal, local
 func (t *translateContext) translateLocalAbsoluteDirectoryPath(ctx context.Context, literal, localFullPath, _ string) (string, error) {
 	info, err := os.Stat(filepath.FromSlash(localFullPath))
 	if errors.Is(err, fs.ErrNotExist) {
+		if t.skipLocalFileValidation {
+			return localFullPath, nil
+		}
 		return "", fmt.Errorf("directory %s not found", literal)
 	}
 	if err != nil {
@@ -311,8 +329,9 @@ func applyTranslations(ctx context.Context, b *bundle.Bundle, t *translateContex
 
 func (m *translatePaths) Apply(ctx context.Context, b *bundle.Bundle) diag.Diagnostics {
 	t := &translateContext{
-		b:    b,
-		seen: make(map[string]string),
+		b:                       b,
+		seen:                    make(map[string]string),
+		skipLocalFileValidation: b.SkipLocalFileValidation,
 	}
 
 	return applyTranslations(ctx, b, t, []func(context.Context, dyn.Value) (dyn.Value, error){
@@ -327,8 +346,9 @@ func (m *translatePaths) Apply(ctx context.Context, b *bundle.Bundle) diag.Diagn
 
 func (m *translatePathsDashboards) Apply(ctx context.Context, b *bundle.Bundle) diag.Diagnostics {
 	t := &translateContext{
-		b:    b,
-		seen: make(map[string]string),
+		b:                       b,
+		seen:                    make(map[string]string),
+		skipLocalFileValidation: b.SkipLocalFileValidation,
 	}
 
 	return applyTranslations(ctx, b, t, []func(context.Context, dyn.Value) (dyn.Value, error){
diff --git a/bundle/config/mutator/translate_paths_test.go b/bundle/config/mutator/translate_paths_test.go
index 299aa45046..396a628770 100644
--- a/bundle/config/mutator/translate_paths_test.go
+++ b/bundle/config/mutator/translate_paths_test.go
@@ -1015,3 +1015,101 @@ func TestTranslatePathsWithSourceLinkedDeployment(t *testing.T) {
 		b.Config.Resources.Pipelines["pipeline"].Libraries[1].Notebook.Path,
 	)
 }
+
+func TestTranslatePathsWithSkipLocalFileValidation(t *testing.T) {
+	dir := t.TempDir()
+	// Intentionally do NOT create any files — paths are stale/missing.
+
+	b := &bundle.Bundle{
+		SyncRootPath:            dir,
+		BundleRootPath:          dir,
+		SyncRoot:                vfs.MustNew(dir),
+		SkipLocalFileValidation: true,
+		Config: config.Root{
+			Workspace: config.Workspace{
+				FilePath: "/bundle",
+			},
+			Resources: config.Resources{
+				Jobs: map[string]*resources.Job{
+					"job": {
+						JobSettings: jobs.JobSettings{
+							Tasks: []jobs.Task{
+								{
+									NotebookTask: &jobs.NotebookTask{
+										NotebookPath: "./src/notebook.py",
+									},
+								},
+								{
+									SparkPythonTask: &jobs.SparkPythonTask{
+										PythonFile: "./src/main.py",
+									},
+								},
+							},
+						},
+					},
+				},
+				Pipelines: map[string]*resources.Pipeline{
+					"pipeline": {
+						CreatePipeline: pipelines.CreatePipeline{
+							Libraries: []pipelines.PipelineLibrary{
+								{
+									Notebook: &pipelines.NotebookLibrary{
+										Path: "./src/pipeline_notebook.py",
+									},
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+	}
+
+	bundletest.SetLocation(b, ".", []dyn.Location{{File: filepath.Join(dir, "databricks.yml")}})
+
+	diags := bundle.ApplySeq(context.Background(), b, mutator.NormalizePaths(), mutator.TranslatePaths())
+	require.NoError(t, diags.Error())
+
+	// Notebook path should be translated (extension stripped) even though file doesn't exist.
+	assert.Equal(t, "/bundle/src/notebook", b.Config.Resources.Jobs["job"].Tasks[0].NotebookTask.NotebookPath)
+
+	// File path should be translated even though file doesn't exist.
+	assert.Equal(t, "/bundle/src/main.py", b.Config.Resources.Jobs["job"].Tasks[1].SparkPythonTask.PythonFile)
+
+	// Pipeline notebook path should be translated even though file doesn't exist.
+	assert.Equal(t, "/bundle/src/pipeline_notebook", b.Config.Resources.Pipelines["pipeline"].Libraries[0].Notebook.Path)
+}
+
+func TestTranslatePathsWithSkipLocalFileValidationDirectory(t *testing.T) {
+	dir := t.TempDir()
+	// Intentionally do NOT create pipeline_root directory.
+
+	b := &bundle.Bundle{
+		SyncRootPath:            dir,
+		BundleRootPath:          dir,
+		SyncRoot:                vfs.MustNew(dir),
+		SkipLocalFileValidation: true,
+		Config: config.Root{
+			Workspace: config.Workspace{
+				FilePath: "/bundle",
+			},
+			Resources: config.Resources{
+				Pipelines: map[string]*resources.Pipeline{
+					"pipeline": {
+						CreatePipeline: pipelines.CreatePipeline{
+							RootPath: "./pipeline_root",
+						},
+					},
+				},
+			},
+		},
+	}
+
+	bundletest.SetLocation(b, ".", []dyn.Location{{File: filepath.Join(dir, "databricks.yml")}})
+
+	diags := bundle.ApplySeq(context.Background(), b, mutator.NormalizePaths(), mutator.TranslatePaths())
+	require.NoError(t, diags.Error())
+
+	// Directory path should be translated even though directory doesn't exist.
+	assert.Equal(t, "/bundle/pipeline_root", b.Config.Resources.Pipelines["pipeline"].RootPath)
+}
diff --git a/cmd/bundle/config_remote_sync.go b/cmd/bundle/config_remote_sync.go
index f131bf4f10..8b99088824 100644
--- a/cmd/bundle/config_remote_sync.go
+++ b/cmd/bundle/config_remote_sync.go
@@ -6,6 +6,7 @@ import (
 	"fmt"
 	"runtime"
 
+	"github.com/databricks/cli/bundle"
 	"github.com/databricks/cli/bundle/configsync"
 	"github.com/databricks/cli/cmd/bundle/utils"
 	"github.com/databricks/cli/cmd/root"
@@ -46,6 +47,9 @@ Examples:
 			ReadState:  true,
 			Build:      true,
 			AlwaysPull: true,
+			InitFunc: func(b *bundle.Bundle) {
+				b.SkipLocalFileValidation = true
+			},
 		})
 		if err != nil {
 			return err