diff --git a/acceptance/bundle/config-remote-sync/job_multiple_tasks/output.txt b/acceptance/bundle/config-remote-sync/job_multiple_tasks/output.txt
index f3350a057f..e1f51e2833 100644
--- a/acceptance/bundle/config-remote-sync/job_multiple_tasks/output.txt
+++ b/acceptance/bundle/config-remote-sync/job_multiple_tasks/output.txt
@@ -69,15 +69,17 @@ Deploying resources...
 Updating deployment state...
 Deployment complete!
 
-=== Rename b_task to b_task_renamed (4 tasks, 2 with depends_on, 1 without)
+=== Rename b_task, replace a_task notebook_path, add synced_task
 === Detect task key rename
 Detected changes in 1 resource(s):
 
 Resource: resources.jobs.rename_task_job
+  tasks[task_key='a_task'].notebook_task.notebook_path: replace
   tasks[task_key='b_task']: remove
   tasks[task_key='b_task_renamed']: add
   tasks[task_key='c_task'].depends_on[0].task_key: replace
   tasks[task_key='d_task'].depends_on[0].task_key: replace
+  tasks[task_key='synced_task']: add
 
 
 
@@ -114,6 +116,22 @@ Resource: resources.jobs.rename_task_job
 +            - task_key: b_task_renamed
            notebook_task:
              notebook_path: /Users/{{workspace_user_name}}/c_task
+@@ -67,7 +67,14 @@
+         - task_key: a_task
+           notebook_task:
+-            notebook_path: /Users/{{workspace_user_name}}/a_task
++            notebook_path: ./synced_notebook.py
+           new_cluster:
+             spark_version: 13.3.x-snapshot-scala2.12
+             node_type_id: [NODE_TYPE_ID]
+             num_workers: 1
++        - new_cluster:
++            node_type_id: [NODE_TYPE_ID]
++            num_workers: 1
++            spark_version: 13.3.x-snapshot-scala2.12
++          notebook_task:
++            notebook_path: ./synced_notebook.py
++          task_key: synced_task
 
 >>> [CLI] bundle destroy --auto-approve
 The following resources will be deleted:
diff --git a/acceptance/bundle/config-remote-sync/job_multiple_tasks/script b/acceptance/bundle/config-remote-sync/job_multiple_tasks/script
index be6d61a4df..10103acb18 100755
--- a/acceptance/bundle/config-remote-sync/job_multiple_tasks/script
+++ b/acceptance/bundle/config-remote-sync/job_multiple_tasks/script
@@ -52,9 +52,9 @@ mv databricks.yml.resolved databricks.yml
 # Deploy the updated configuration to sync state
 $CLI bundle deploy
 
-title "Rename b_task to b_task_renamed (4 tasks, 2 with depends_on, 1 without)"
+title "Rename b_task, replace a_task notebook_path, add synced_task"
 rename_job_id="$(read_id.py rename_task_job)"
-edit_resource.py jobs $rename_job_id <<'EOF'
+edit_resource.py jobs $rename_job_id <<EOF
 for task in r["tasks"]:
     if task["task_key"] == "b_task":
         task["task_key"] = "b_task_renamed"
@@ -62,6 +62,24 @@ for task in r["tasks"]:
         for dep in task["depends_on"]:
             if dep["task_key"] == "b_task":
                 dep["task_key"] = "b_task_renamed"
+
+# Replace a_task's notebook_path with sync-root path (tests Replace operation)
+for task in r["tasks"]:
+    if task["task_key"] == "a_task":
+        task["notebook_task"]["notebook_path"] = "${PWD}/synced_notebook"
+
+# Add synced_task with path inside sync root
+r["tasks"].append({
+    "task_key": "synced_task",
+    "notebook_task": {
+        "notebook_path": "${PWD}/synced_notebook"
+    },
+    "new_cluster": {
+        "spark_version": "${DEFAULT_SPARK_VERSION}",
+        "node_type_id": "${NODE_TYPE_ID}",
+        "num_workers": 1
+    }
+})
 EOF
 
 title "Detect task key rename"
diff --git a/acceptance/bundle/config-remote-sync/job_multiple_tasks/synced_notebook.py b/acceptance/bundle/config-remote-sync/job_multiple_tasks/synced_notebook.py
new file mode 100644
index 0000000000..1645e04b1d
--- /dev/null
+++ b/acceptance/bundle/config-remote-sync/job_multiple_tasks/synced_notebook.py
@@ -0,0 +1 @@
+# Databricks notebook source
diff --git a/acceptance/bundle/config-remote-sync/job_multiple_tasks/test.toml b/acceptance/bundle/config-remote-sync/job_multiple_tasks/test.toml
index 3894d66826..c227fcbe56 100644
--- a/acceptance/bundle/config-remote-sync/job_multiple_tasks/test.toml
+++ b/acceptance/bundle/config-remote-sync/job_multiple_tasks/test.toml
@@ -1,7 +1,7 @@
 Cloud = true
 
 RecordRequests = false
-Ignore = [".databricks", "dummy.whl", "databricks.yml", "databricks.yml.backup"]
+Ignore = [".databricks", "dummy.whl", "databricks.yml", "databricks.yml.backup", "synced_notebook.py"]
 
 [Env]
 DATABRICKS_BUNDLE_ENABLE_EXPERIMENTAL_YAML_SYNC = "true"
diff --git a/acceptance/bundle/config-remote-sync/multiple_files/output.txt b/acceptance/bundle/config-remote-sync/multiple_files/output.txt
index 959d8e9066..e616ca008c 100644
--- a/acceptance/bundle/config-remote-sync/multiple_files/output.txt
+++ b/acceptance/bundle/config-remote-sync/multiple_files/output.txt
@@ -4,6 +4,7 @@ Updating deployment state...
 Deployment complete!
 
 === Modify job_one: max_concurrent_runs, rename c_task
+=== Add synced_task to job_one (notebook in sync root, resource in subdirectory)
 === Modify job_two: max_concurrent_runs, rename first task, add extra_task
 === Add extra_task to local config (not in saved state, triggers entity-level replace)
 === Detect and save changes
@@ -14,6 +15,7 @@ Resource: resources.jobs.job_one
   tasks[task_key='a_task'].depends_on[0].task_key: replace
   tasks[task_key='c_task']: remove
   tasks[task_key='c_task_renamed']: add
+  tasks[task_key='synced_task']: add
 
 Resource: resources.jobs.job_two
   max_concurrent_runs: replace
@@ -50,11 +52,18 @@ Resource: resources.jobs.job_two
 +          task_key: c_task_renamed
          - task_key: a_task
            notebook_task:
-@@ -21,3 +21,3 @@
+@@ -21,3 +21,10 @@
              num_workers: 1
            depends_on:
 -            - task_key: c_task
 +            - task_key: c_task_renamed
++        - new_cluster:
++            node_type_id: [NODE_TYPE_ID]
++            num_workers: 1
++            spark_version: 13.3.x-snapshot-scala2.12
++          notebook_task:
++            notebook_path: ../sample_exploration.ipynb
++          task_key: synced_task
 
 === Changes in job2.yml
 
diff --git a/acceptance/bundle/config-remote-sync/multiple_files/sample_exploration.ipynb b/acceptance/bundle/config-remote-sync/multiple_files/sample_exploration.ipynb
new file mode 100644
index 0000000000..b83ee2a9ab
--- /dev/null
+++ b/acceptance/bundle/config-remote-sync/multiple_files/sample_exploration.ipynb
@@ -0,0 +1,63 @@
+{
+ "cells": [
+  {
+   "cell_type": "markdown",
+   "metadata": {
+    "application/vnd.databricks.v1+cell": {
+     "cellMetadata": {},
+     "inputWidgets": {},
+     "nuid": "[UUID]",
+     "showTitle": false,
+     "tableResultSettingsMap": {},
+     "title": ""
+    }
+   },
+   "source": [
+    "### Example Exploratory Notebook\n",
+    "\n",
+    "Use this notebook to explore the data generated by the pipeline in your preferred programming language.\n",
+    "\n",
+    "**Note**: This notebook is not executed as part of the pipeline."
+   ]
+  },
+  {
+   "cell_type": "code",
+   "execution_count": 0,
+   "metadata": {
+    "application/vnd.databricks.v1+cell": {
+     "cellMetadata": {},
+     "inputWidgets": {},
+     "nuid": "[UUID]",
+     "showTitle": false,
+     "tableResultSettingsMap": {},
+     "title": ""
+    }
+   },
+   "outputs": [],
+   "source": [
+    "# !!! Before performing any data analysis, make sure to run the pipeline to materialize the sample datasets. The tables referenced in this notebook depend on that step.\n",
+    "\n",
+    "display(spark.sql(\"SELECT * FROM hive_metastore.[USERNAME].sample_trips_lakeflow_project\"))"
+   ]
+  }
+ ],
+ "metadata": {
+  "application/vnd.databricks.v1+notebook": {
+   "computePreferences": null,
+   "dashboards": [],
+   "environmentMetadata": null,
+   "inputWidgetPreferences": null,
+   "language": "python",
+   "notebookMetadata": {
+    "pythonIndentUnit": 2
+   },
+   "notebookName": "sample_exploration",
+   "widgets": {}
+  },
+  "language_info": {
+   "name": "python"
+  }
+ },
+ "nbformat": 4,
+ "nbformat_minor": 0
+}
diff --git a/acceptance/bundle/config-remote-sync/multiple_files/script b/acceptance/bundle/config-remote-sync/multiple_files/script
index d66bb7bbbf..4316a3f1cc 100755
--- a/acceptance/bundle/config-remote-sync/multiple_files/script
+++ b/acceptance/bundle/config-remote-sync/multiple_files/script
@@ -27,6 +27,21 @@ for task in r["tasks"]:
                 dep["task_key"] = "c_task_renamed"
 EOF
 
+title "Add synced_task to job_one (notebook in sync root, resource in subdirectory)"
+edit_resource.py jobs $job_one_id <<EOF
+r["tasks"].append({
+    "task_key": "synced_task",
+    "notebook_task": {
+        "notebook_path": "${PWD}/sample_exploration"
+    },
+    "new_cluster": {
+        "spark_version": "${DEFAULT_SPARK_VERSION}",
+        "node_type_id": "${NODE_TYPE_ID}",
+        "num_workers": 1
+    }
+})
+EOF
+
 title "Modify job_two: max_concurrent_runs, rename first task, add extra_task"
 edit_resource.py jobs $job_two_id <<'EOF'
 r["max_concurrent_runs"] = 10
diff --git a/acceptance/bundle/config-remote-sync/multiple_files/test.toml b/acceptance/bundle/config-remote-sync/multiple_files/test.toml
index 47f57bbbc6..b8b496456d 100644
--- a/acceptance/bundle/config-remote-sync/multiple_files/test.toml
+++ b/acceptance/bundle/config-remote-sync/multiple_files/test.toml
@@ -1,7 +1,7 @@
 Cloud = true
 
 RecordRequests = false
-Ignore = [".databricks", "dummy.whl", "databricks.yml", "resources/job1.yml", "resources/job2.yml"]
+Ignore = [".databricks", "dummy.whl", "databricks.yml", "resources/job1.yml", "resources/job2.yml", "sample_exploration.ipynb"]
 
 [Env]
 DATABRICKS_BUNDLE_ENABLE_EXPERIMENTAL_YAML_SYNC = "true"
diff --git a/acceptance/bundle/config-remote-sync/pipeline_fields/output.txt b/acceptance/bundle/config-remote-sync/pipeline_fields/output.txt
index d536597186..09d5f382e7 100644
--- a/acceptance/bundle/config-remote-sync/pipeline_fields/output.txt
+++ b/acceptance/bundle/config-remote-sync/pipeline_fields/output.txt
@@ -12,6 +12,7 @@ Resource: resources.pipelines.my_pipeline
   environment.dependencies: replace
   notifications[0].alerts: replace
   notifications[0].email_recipients: replace
+  root_path: add
   schema: replace
   tags['foo']: add
 
@@ -28,7 +29,7 @@ Resource: resources.pipelines.my_pipeline
 -
  resources:
    pipelines:
-@@ -7,19 +6,24 @@
+@@ -7,19 +6,25 @@
        name: test-pipeline-[UNIQUE_NAME]
        catalog: main
 -      schema: default
@@ -53,6 +54,7 @@ Resource: resources.pipelines.my_pipeline
 -
 +      tags:
 +        foo: bar
++      root_path: ./pipeline_root
  targets:
    default:
 
diff --git a/acceptance/bundle/config-remote-sync/pipeline_fields/pipeline_root/.gitkeep b/acceptance/bundle/config-remote-sync/pipeline_fields/pipeline_root/.gitkeep
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/acceptance/bundle/config-remote-sync/pipeline_fields/script b/acceptance/bundle/config-remote-sync/pipeline_fields/script
index 69e2c87b7c..a83b940966 100755
--- a/acceptance/bundle/config-remote-sync/pipeline_fields/script
+++ b/acceptance/bundle/config-remote-sync/pipeline_fields/script
@@ -17,6 +17,7 @@ r["configuration"]["key2"] = "value2"
 r["notifications"][0]["email_recipients"].append("admin@example.com")
 r["notifications"][0]["alerts"].append("on-update-failure")
 r["schema"] = "prod"
+r["root_path"] = "${PWD}/pipeline_root"
 if "tags" not in r:
     r["tags"] = {}
 r["tags"]["foo"] = "bar"
diff --git a/acceptance/bundle/config-remote-sync/pipeline_fields/test.toml b/acceptance/bundle/config-remote-sync/pipeline_fields/test.toml
index 3174477f7d..f307000e06 100644
--- a/acceptance/bundle/config-remote-sync/pipeline_fields/test.toml
+++ b/acceptance/bundle/config-remote-sync/pipeline_fields/test.toml
@@ -2,7 +2,7 @@ Cloud = true
 RequiresUnityCatalog = true
 
 RecordRequests = false
-Ignore = [".databricks", "databricks.yml", "databricks.yml.backup"]
+Ignore = [".databricks", "databricks.yml", "databricks.yml.backup", "pipeline_root"]
 
 [Env]
 DATABRICKS_BUNDLE_ENABLE_EXPERIMENTAL_YAML_SYNC = "true"
diff --git a/bundle/config/mutator/translate_paths.go b/bundle/config/mutator/translate_paths.go
index 86f0601875..213bf37fad 100644
--- a/bundle/config/mutator/translate_paths.go
+++ b/bundle/config/mutator/translate_paths.go
@@ -184,29 +184,21 @@ func (t *translateContext) translateNotebookPath(ctx context.Context, literal, l
 			return "", fmt.Errorf("notebook %s not found", literal)
 		}
 
-		extensions := []string{
-			notebook.ExtensionPython,
-			notebook.ExtensionR,
-			notebook.ExtensionScala,
-			notebook.ExtensionSql,
-			notebook.ExtensionJupyter,
-		}
-
 		// Check whether a file with a notebook extension already exists. This
 		// way we can provide a more targeted error message.
-		for _, ext := range extensions {
+		for _, ext := range notebook.Extensions {
 			literalWithExt := literal + ext
 			localRelPathWithExt := localRelPath + ext
 			if _, err := fs.Stat(t.b.SyncRoot, localRelPathWithExt); err == nil {
 				return "", fmt.Errorf(`notebook %q not found. Did you mean %q?
 Local notebook references are expected to contain one of the following
-file extensions: [%s]`, literal, literalWithExt, strings.Join(extensions, ", "))
+file extensions: [%s]`, literal, literalWithExt, strings.Join(notebook.Extensions, ", "))
 			}
 		}
 
 		// Return a generic error message if no matching possible file is found.
 		return "", fmt.Errorf(`notebook %q not found. Local notebook references are expected
-to contain one of the following file extensions: [%s]`, literal, strings.Join(extensions, ", "))
+to contain one of the following file extensions: [%s]`, literal, strings.Join(notebook.Extensions, ", "))
 	}
 	if err != nil {
 		return "", fmt.Errorf("unable to determine if %s is a notebook: %w", localFullPath, err)
diff --git a/bundle/configsync/resolve.go b/bundle/configsync/resolve.go
index 72fca35956..396480111f 100644
--- a/bundle/configsync/resolve.go
+++ b/bundle/configsync/resolve.go
@@ -3,11 +3,15 @@ package configsync
 import (
 	"context"
 	"fmt"
+	"io/fs"
+	"path/filepath"
 	"sort"
+	"strings"
 
 	"github.com/databricks/cli/bundle"
 	"github.com/databricks/cli/libs/dyn"
 	"github.com/databricks/cli/libs/log"
+	"github.com/databricks/cli/libs/notebook"
 	"github.com/databricks/cli/libs/structs/structpath"
 )
 
@@ -284,6 +288,13 @@ func ResolveChanges(ctx context.Context, b *bundle.Bundle, configChanges Changes
 				log.Debugf(ctx, "Field %s has no location, using resource location: %s", fullPath, filePath)
 			}
 
+			if (configChange.Operation == OperationAdd || configChange.Operation == OperationReplace) && b.SyncRootPath != "" {
+				configChange = &ConfigChangeDesc{
+					Operation: configChange.Operation,
+					Value:     translateWorkspacePaths(configChange.Value, b.SyncRootPath, b.SyncRoot, filepath.Dir(filePath)),
+				}
+			}
+
 			result = append(result, FieldChange{
 				FilePath:        filePath,
 				Change:          configChange,
@@ -294,3 +305,59 @@ func ResolveChanges(ctx context.Context, b *bundle.Bundle, configChanges Changes
 
 	return result, nil
 }
+
+// translateWorkspacePaths recursively converts absolute workspace paths to relative
+// paths when they fall within the bundle's sync root. Paths are made relative to
+// targetDir (the directory of the YAML file being patched). For notebook paths
+// where the extension was stripped by translate_paths, it restores the extension
+// by checking the local filesystem.
+func translateWorkspacePaths(value any, syncRootPath string, syncRoot fs.FS, targetDir string) any {
+	switch v := value.(type) {
+	case string:
+		after, ok := strings.CutPrefix(v, syncRootPath+"/")
+		if !ok {
+			return v
+		}
+		after = resolveNotebookExtension(syncRoot, after)
+		fullPath := filepath.Join(syncRootPath, after)
+		relPath, err := filepath.Rel(targetDir, fullPath)
+		if err != nil {
+			return "./" + after
+		}
+		relPathSlash := filepath.ToSlash(relPath)
+		if !strings.HasPrefix(relPathSlash, "..") {
+			relPathSlash = "./" + relPathSlash
+		}
+		return relPathSlash
+	case map[string]any:
+		for key, val := range v {
+			v[key] = translateWorkspacePaths(val, syncRootPath, syncRoot, targetDir)
+		}
+		return v
+	case []any:
+		for i, val := range v {
+			v[i] = translateWorkspacePaths(val, syncRootPath, syncRoot, targetDir)
+		}
+		return v
+	default:
+		return value
+	}
+}
+
+// resolveNotebookExtension checks if a relative path refers to a notebook whose
+// extension was stripped by translate_paths. If the file doesn't exist as-is but
+// exists with a notebook extension, the extension is appended.
+func resolveNotebookExtension(syncRoot fs.FS, relPath string) string {
+	if syncRoot == nil {
+		return relPath
+	}
+	if _, err := fs.Stat(syncRoot, relPath); err == nil {
+		return relPath
+	}
+	for _, ext := range notebook.Extensions {
+		if _, err := fs.Stat(syncRoot, relPath+ext); err == nil {
+			return relPath + ext
+		}
+	}
+	return relPath
+}
diff --git a/libs/notebook/ext.go b/libs/notebook/ext.go
index c34ad2cc9e..bbffe23c2d 100644
--- a/libs/notebook/ext.go
+++ b/libs/notebook/ext.go
@@ -11,6 +11,15 @@ const (
 	ExtensionJupyter string = ".ipynb"
 )
 
+// Extensions lists all notebook file extensions.
+var Extensions = []string{
+	ExtensionPython,
+	ExtensionR,
+	ExtensionScala,
+	ExtensionSql,
+	ExtensionJupyter,
+}
+
 var ExtensionToLanguage = map[string]workspace.Language{
 	ExtensionPython: workspace.LanguagePython,
 	ExtensionR:      workspace.LanguageR,