diff --git a/packages/core/src/execution-engine/__tests__/execution-context.test.ts b/packages/core/src/execution-engine/__tests__/execution-context.test.ts
new file mode 100644
index 00000000000..e18b6096cad
--- /dev/null
+++ b/packages/core/src/execution-engine/__tests__/execution-context.test.ts
@@ -0,0 +1,345 @@
+import { mock } from 'jest-mock-extended';
+import {
+	UnexpectedError,
+	type INode,
+	type IRunExecutionData,
+	type IWorkflowExecuteAdditionalData,
+	type Workflow,
+	type WorkflowExecuteMode,
+} from 'n8n-workflow';
+
+import { establishExecutionContext } from '../execution-context';
+
+describe('establishExecutionContext', () => {
+	const mockWorkflow = mock<Workflow>({ id: 'test-workflow-id' });
+	const mockAdditionalData = mock<IWorkflowExecuteAdditionalData>();
+	const mockMode: WorkflowExecuteMode = 'manual';
+
+	describe('successful context establishment', () => {
+		it('should establish context with version 1 and timestamp', async () => {
+			const startNode = mock<INode>({ name: 'Start', type: 'n8n-nodes-base.start' });
+			const runExecutionData: IRunExecutionData = {
+				startData: {},
+				resultData: {
+					runData: {},
+				},
+				executionData: {
+					contextData: {},
+					nodeExecutionStack: [
+						{
+							node: startNode,
+							data: {
+								main: [[{ json: {} }]],
+							},
+							source: null,
+						},
+					],
+					metadata: {},
+					waitingExecution: {},
+					waitingExecutionSource: {},
+				},
+			};
+
+			const beforeTimestamp = Date.now();
+			await establishExecutionContext(mockWorkflow, runExecutionData, mockAdditionalData, mockMode);
+			const afterTimestamp = Date.now();
+
+			expect(runExecutionData.executionData!.runtimeData).toBeDefined();
+			expect(runExecutionData.executionData!.runtimeData).toHaveProperty('version', 1);
+			expect(runExecutionData.executionData!.runtimeData).toHaveProperty('establishedAt');
+			expect(runExecutionData.executionData!.runtimeData).toHaveProperty('source', 'manual');
+
+			const establishedAt = runExecutionData.executionData!.runtimeData!.establishedAt;
+			expect(establishedAt).toBeGreaterThanOrEqual(beforeTimestamp);
+			expect(establishedAt).toBeLessThanOrEqual(afterTimestamp);
+		});
+
+		it('should mutate the provided runExecutionData object', async () => {
+			const startNode = mock<INode>({ name: 'Start', type: 'n8n-nodes-base.start' });
+			const runExecutionData: IRunExecutionData = {
+				startData: {},
+				resultData: {
+					runData: {},
+				},
+				executionData: {
+					contextData: {},
+					nodeExecutionStack: [
+						{
+							node: startNode,
+							data: {
+								main: [[{ json: {} }]],
+							},
+							source: null,
+						},
+					],
+					metadata: {},
+					waitingExecution: {},
+					waitingExecutionSource: {},
+				},
+			};
+
+			const referenceBefore = runExecutionData.executionData;
+			await establishExecutionContext(mockWorkflow, runExecutionData, mockAdditionalData, mockMode);
+			const referenceAfter = runExecutionData.executionData;
+
+			// Verify the same object reference is used (mutation, not replacement)
+			expect(referenceBefore).toBe(referenceAfter);
+			expect(runExecutionData.executionData!.runtimeData).toBeDefined();
+		});
+
+		it('should establish context when execution stack has multiple nodes', async () => {
+			const startNode = mock<INode>({ name: 'Start', type: 'n8n-nodes-base.start' });
+			const secondNode = mock<INode>({ name: 'Second', type: 'n8n-nodes-base.set' });
+			const runExecutionData: IRunExecutionData = {
+				startData: {},
+				resultData: {
+					runData: {},
+				},
+				executionData: {
+					contextData: {},
+					nodeExecutionStack: [
+						{
+							node: startNode,
+							data: {
+								main: [[{ json: {} }]],
+							},
+							source: null,
+						},
+						{
+							node: secondNode,
+							data: {
+								main: [[{ json: {} }]],
+							},
+							source: null,
+						},
+					],
+					metadata: {},
+					waitingExecution: {},
+					waitingExecutionSource: {},
+				},
+			};
+
+			await establishExecutionContext(mockWorkflow, runExecutionData, mockAdditionalData, mockMode);
+
+			expect(runExecutionData.executionData!.runtimeData).toBeDefined();
+			expect(runExecutionData.executionData!.runtimeData!.version).toBe(1);
+		});
+	});
+
+	describe('Chat Trigger workflow support', () => {
+		it('should establish basic context for empty execution stack (Chat Trigger)', async () => {
+			const runExecutionData: IRunExecutionData = {
+				startData: {},
+				resultData: {
+					runData: {},
+				},
+				executionData: {
+					contextData: {},
+					nodeExecutionStack: [], // Empty stack - Chat Trigger workflow
+					metadata: {},
+					waitingExecution: {},
+					waitingExecutionSource: {},
+				},
+			};
+
+			const beforeTimestamp = Date.now();
+			await establishExecutionContext(mockWorkflow, runExecutionData, mockAdditionalData, mockMode);
+			const afterTimestamp = Date.now();
+
+			// Should establish basic context even with empty stack
+			expect(runExecutionData.executionData!.runtimeData).toBeDefined();
+			expect(runExecutionData.executionData!.runtimeData!.version).toBe(1);
+			expect(runExecutionData.executionData!.runtimeData!.source).toBe('manual');
+			expect(runExecutionData.executionData!.runtimeData!.establishedAt).toBeGreaterThanOrEqual(
+				beforeTimestamp,
+			);
+			expect(runExecutionData.executionData!.runtimeData!.establishedAt).toBeLessThanOrEqual(
+				afterTimestamp,
+			);
+		});
+
+		it('should establish basic context without start node extraction for Chat Trigger', async () => {
+			const runExecutionData: IRunExecutionData = {
+				startData: {},
+				resultData: {
+					runData: {},
+				},
+				executionData: {
+					contextData: {},
+					nodeExecutionStack: [], // Empty stack
+					metadata: {},
+					waitingExecution: {},
+					waitingExecutionSource: {},
+				},
+			};
+
+			await establishExecutionContext(mockWorkflow, runExecutionData, mockAdditionalData, mockMode);
+
+			const context = runExecutionData.executionData!.runtimeData;
+
+			// Verify context has only basic properties (no start-node-specific extraction)
+			expect(Object.keys(context!)).toEqual(['version', 'establishedAt', 'source']);
+			expect(typeof context!.version).toBe('number');
+			expect(typeof context!.establishedAt).toBe('number');
+			expect(context!.source).toBe('manual');
+		});
+	});
+
+	describe('error handling', () => {
+		it('should throw error when executionData is missing', async () => {
+			const runExecutionData: IRunExecutionData = {
+				startData: {},
+				resultData: {
+					runData: {},
+				},
+				// executionData is missing
+			};
+
+			await expect(
+				establishExecutionContext(mockWorkflow, runExecutionData, mockAdditionalData, mockMode),
+			).rejects.toThrow(UnexpectedError);
+		});
+
+		it('should throw error when executionData is undefined', async () => {
+			const runExecutionData: IRunExecutionData = {
+				startData: {},
+				resultData: {
+					runData: {},
+				},
+				executionData: undefined,
+			};
+
+			await expect(
+				establishExecutionContext(mockWorkflow, runExecutionData, mockAdditionalData, mockMode),
+			).rejects.toThrow(UnexpectedError);
+		});
+	});
+
+	describe('context structure validation', () => {
+		it('should create context with correct structure', async () => {
+			const startNode = mock<INode>({ name: 'Webhook', type: 'n8n-nodes-base.webhook' });
+			const runExecutionData: IRunExecutionData = {
+				startData: {},
+				resultData: {
+					runData: {},
+				},
+				executionData: {
+					contextData: {},
+					nodeExecutionStack: [
+						{
+							node: startNode,
+							data: {
+								main: [[{ json: { test: 'data' } }]],
+							},
+							source: null,
+						},
+					],
+					metadata: {},
+					waitingExecution: {},
+					waitingExecutionSource: {},
+				},
+			};
+
+			await establishExecutionContext(mockWorkflow, runExecutionData, mockAdditionalData, mockMode);
+
+			const context = runExecutionData.executionData!.runtimeData;
+
+			// Verify context has only expected properties
+			expect(Object.keys(context!)).toEqual(['version', 'establishedAt', 'source']);
+			expect(typeof context!.version).toBe('number');
+			expect(typeof context!.establishedAt).toBe('number');
+			expect(context!.source).toBe('manual');
+		});
+
+		it('should create unique timestamps for different executions', async () => {
+			const startNode = mock<INode>({ name: 'Start', type: 'n8n-nodes-base.start' });
+
+			const runExecutionData1: IRunExecutionData = {
+				startData: {},
+				resultData: { runData: {} },
+				executionData: {
+					contextData: {},
+					nodeExecutionStack: [
+						{
+							node: startNode,
+							data: { main: [[{ json: {} }]] },
+							source: null,
+						},
+					],
+					metadata: {},
+					waitingExecution: {},
+					waitingExecutionSource: {},
+				},
+			};
+
+			const runExecutionData2: IRunExecutionData = {
+				startData: {},
+				resultData: { runData: {} },
+				executionData: {
+					contextData: {},
+					nodeExecutionStack: [
+						{
+							node: startNode,
+							data: { main: [[{ json: {} }]] },
+							source: null,
+						},
+					],
+					metadata: {},
+					waitingExecution: {},
+					waitingExecutionSource: {},
+				},
+			};
+
+			await establishExecutionContext(
+				mockWorkflow,
+				runExecutionData1,
+				mockAdditionalData,
+				mockMode,
+			);
+			// Small delay to ensure different timestamps
+			await new Promise((resolve) => setTimeout(resolve, 5));
+			await establishExecutionContext(
+				mockWorkflow,
+				runExecutionData2,
+				mockAdditionalData,
+				mockMode,
+			);
+
+			const timestamp1 = runExecutionData1.executionData!.runtimeData!.establishedAt;
+			const timestamp2 = runExecutionData2.executionData!.runtimeData!.establishedAt;
+
+			expect(timestamp1).toBeLessThan(timestamp2);
+		});
+
+		it('should work with different execution modes', async () => {
+			const startNode = mock<INode>({ name: 'Trigger', type: 'n8n-nodes-base.cron' });
+			const modes: WorkflowExecuteMode[] = ['manual', 'trigger', 'webhook'];
+
+			for (const mode of modes) {
+				const runExecutionData: IRunExecutionData = {
+					startData: {},
+					resultData: { runData: {} },
+					executionData: {
+						contextData: {},
+						nodeExecutionStack: [
+							{
+								node: startNode,
+								data: { main: [[{ json: {} }]] },
+								source: null,
+							},
+						],
+						metadata: {},
+						waitingExecution: {},
+						waitingExecutionSource: {},
+					},
+				};
+
+				await establishExecutionContext(mockWorkflow, runExecutionData, mockAdditionalData, mode);
+
+				expect(runExecutionData.executionData!.runtimeData).toBeDefined();
+				expect(runExecutionData.executionData!.runtimeData!.version).toBe(1);
+				expect(runExecutionData.executionData!.runtimeData!.source).toBe(mode);
+			}
+		});
+	});
+});
diff --git a/packages/core/src/execution-engine/__tests__/workflow-execute.test.ts b/packages/core/src/execution-engine/__tests__/workflow-execute.test.ts
index 74f37645a20..91ef4c0bdd4 100644
--- a/packages/core/src/execution-engine/__tests__/workflow-execute.test.ts
+++ b/packages/core/src/execution-engine/__tests__/workflow-execute.test.ts
@@ -122,6 +122,14 @@ describe('WorkflowExecute', () => {
 				expect(result.finished).toEqual(true);
 				expect(result.data.executionData!.contextData).toEqual({});
 				expect(result.data.executionData!.nodeExecutionStack).toEqual([]);
+				// Check if execution context was established
+				expect(result.data.executionData!.runtimeData).toBeDefined();
+				expect(result.data.executionData!.runtimeData).toHaveProperty('version', 1);
+				expect(result.data.executionData!.runtimeData).toHaveProperty('establishedAt');
+				expect(result.data.executionData!.runtimeData).toHaveProperty('source');
+				expect(result.data.executionData!.runtimeData!.source).toEqual('manual');
+				expect(typeof result.data.executionData!.runtimeData!.establishedAt).toBe('number');
+				expect(result.data.executionData!.runtimeData!.establishedAt).toBeGreaterThan(0);
 			});
 		}
 	});
@@ -191,6 +199,15 @@ describe('WorkflowExecute', () => {
 				expect(result.finished).toEqual(true);
 				expect(result.data.executionData!.contextData).toEqual({});
 				expect(result.data.executionData!.nodeExecutionStack).toEqual([]);
+
+				// Check if execution context was established
+				expect(result.data.executionData!.runtimeData).toBeDefined();
+				expect(result.data.executionData!.runtimeData).toHaveProperty('version', 1);
+				expect(result.data.executionData!.runtimeData).toHaveProperty('establishedAt');
+				expect(result.data.executionData!.runtimeData).toHaveProperty('source');
+				expect(result.data.executionData!.runtimeData!.source).toEqual('manual');
+				expect(typeof result.data.executionData!.runtimeData!.establishedAt).toBe('number');
+				expect(result.data.executionData!.runtimeData!.establishedAt).toBeGreaterThan(0);
 			});
 		}
 	});
@@ -405,6 +422,15 @@ describe('WorkflowExecute', () => {
 				expect(result.finished).toEqual(true);
 				// expect(result.data.executionData!.contextData).toEqual({}); //Fails when test workflow Includes splitInbatches
 				expect(result.data.executionData!.nodeExecutionStack).toEqual([]);
+
+				// Check if execution context was established
+				expect(result.data.executionData!.runtimeData).toBeDefined();
+				expect(result.data.executionData!.runtimeData).toHaveProperty('version', 1);
+				expect(result.data.executionData!.runtimeData).toHaveProperty('establishedAt');
+				expect(result.data.executionData!.runtimeData).toHaveProperty('source');
+				expect(result.data.executionData!.runtimeData!.source).toEqual('manual');
+				expect(typeof result.data.executionData!.runtimeData!.establishedAt).toBe('number');
+				expect(result.data.executionData!.runtimeData!.establishedAt).toBeGreaterThan(0);
 			});
 		}
 	});
diff --git a/packages/core/src/execution-engine/execution-context.ts b/packages/core/src/execution-engine/execution-context.ts
new file mode 100644
index 00000000000..32d6c941159
--- /dev/null
+++ b/packages/core/src/execution-engine/execution-context.ts
@@ -0,0 +1,119 @@
+import {
+	type IWorkflowExecuteAdditionalData,
+	type WorkflowExecuteMode,
+	type IRunExecutionData,
+	type Workflow,
+} from 'n8n-workflow';
+
+import { assertExecutionDataExists } from '@/utils/assertions';
+
+/**
+ * Establishes the execution context for a workflow run.
+ *
+ * This function creates and initializes the execution context that persists throughout
+ * the workflow execution lifecycle. The context is stored directly in the provided
+ * `runExecutionData.executionData.runtimeData` object.
+ *
+ * @param workflow - The workflow instance being executed (reserved for future context extraction)
+ * @param runExecutionData - The execution data structure that will be mutated to include the execution context
+ * @param additionalData - Additional workflow execution data used for validation and future context extraction
+ * @param mode - The workflow execution mode (manual, trigger, webhook, etc.)
+ *
+ * @returns Promise that resolves when context has been established
+ *
+ * @throws {UnexpectedError} When `runExecutionData.executionData` is missing or invalid
+ *
+ * @remarks
+ * ## Mutation Behavior
+ * This function mutates the provided `runExecutionData` object by setting:
+ * - `runExecutionData.executionData.runtimeData` with the newly created execution context
+ *
+ * ## Context Creation
+ * - Creates a new context with version 1 schema and current timestamp
+ * - Establishes basic context for all workflows (including Chat Trigger workflows)
+ * - Supports future extraction of context information from start node (when available)
+ * - Validates execution data structure before context creation
+ *
+ * ## Chat Trigger Support
+ * Workflows containing only Chat Trigger nodes have an empty `nodeExecutionStack`.
+ * In such cases, basic context (version + timestamp) is still established, but no
+ * start-node-specific context extraction is performed.
+ *
+ * ## Future Enhancements
+ * The function is designed to support extracting context information from:
+ * - Start node parameters (e.g., webhook authentication tokens)
+ * - Start node type (trigger, manual, webhook, etc.)
+ * - Input data from triggering events
+ * - User identification from various sources
+ *
+ * ## Example Usage
+ * ```typescript
+ * await establishExecutionContext(workflow, runExecutionData, additionalData, mode);
+ * // Context is now available in: runExecutionData.executionData.runtimeData
+ * ```
+ *
+ * @see IExecutionContextV1 for context structure definition
+ * @see IRunExecutionData for execution data structure
+ * @see IWorkflowExecuteAdditionalData for additional execution data
+ */
+export const establishExecutionContext = async (
+	workflow: Workflow,
+	runExecutionData: IRunExecutionData,
+	additionalData: IWorkflowExecuteAdditionalData,
+	mode: WorkflowExecuteMode,
+): Promise<void> => {
+	assertExecutionDataExists(runExecutionData.executionData, workflow, additionalData, mode);
+
+	const executionData = runExecutionData.executionData;
+
+	// At this point we have established the basic execution context.
+	// If a context is already established we overwrite it.
+	// This might change depending on the propagation strategy we want to implement in the future.
+	executionData.runtimeData = {
+		version: 1,
+		establishedAt: Date.now(),
+		source: mode,
+	};
+
+	// Next, we attempt to extract additional context from the start node of the execution stack.
+	const [startItem] = executionData.nodeExecutionStack;
+
+	// The nodeExecutionStack is typically initialized in one of three ways:
+	// 1. run() method: Creates stack with start node (workflow-execute.ts:143-157)
+	// 2. runPartialWorkflow2(): Recreates stack from existing runData via recreateNodeExecutionStack()
+	// 3. Constructor with executionData: Pre-populated from caller (resume scenarios)
+	//
+	// However, the stack CAN be legitimately empty for workflows containing only Chat Trigger nodes
+	// (see workflow-execute.ts:1368-1369). In such cases, we cannot extract context from a start
+	// node, but we should still establish basic execution context.
+	//
+	// We cannot extract user specific information from the initial item though. So we exit early.
+	if (!startItem) {
+		return;
+	}
+
+	// TODO: the following comments will be implemented in future iterations
+	// to extract more context information based on the start node
+	// and the data that triggered the workflow execution.
+	// the comments are left here for now to provide more context on how
+	// this can be achieved.
+
+	// startNodeParameters will hold the parameters of the start node
+	// this can be the settings for the different hooks to be executed
+	// for example to extract the bearer token from the start node data.
+
+	// const startNodeParameters = startItem.node.parameters;
+
+	// startNodeType holds the type of the start node
+
+	// const startNodeType = startItem.node.type;
+
+	// Main input data is an array of items, each item represents an event that triggers the workflow execution
+	// The 'main' selector selects the input name of the nodes, and the 0 index represents the runIndex,
+	// 0 being the first run of this node in the workflow.
+
+	// const mainInput = startItem.data["main"][0];
+
+	// based on startNodeParameters, startNodeType and mainInput we can now
+	// iterate over the different hooks to extract specific data for the runtime context
+};
diff --git a/packages/core/src/execution-engine/workflow-execute.ts b/packages/core/src/execution-engine/workflow-execute.ts
index 750f3e080a4..1f4a7706d5d 100644
--- a/packages/core/src/execution-engine/workflow-execute.ts
+++ b/packages/core/src/execution-engine/workflow-execute.ts
@@ -59,8 +59,10 @@ import PCancelable from 'p-cancelable';
 import { ErrorReporter } from '@/errors/error-reporter';
 import { WorkflowHasIssuesError } from '@/errors/workflow-has-issues.error';
 import * as NodeExecuteFunctions from '@/node-execute-functions';
+import { assertExecutionDataExists } from '@/utils/assertions';
 import { isJsonCompatible } from '@/utils/is-json-compatible';
 
+import { establishExecutionContext } from './execution-context';
 import type { ExecutionLifecycleHooks } from './execution-lifecycle-hooks';
 import { ExecuteContext, PollContext } from './node-execution-context';
 import {
@@ -1325,22 +1327,6 @@ export class WorkflowExecute {
 		);
 	}
 
-	private assertExecutionDataExists(
-		this: WorkflowExecute,
-		executionData: IRunExecutionData['executionData'],
-		workflow: Workflow,
-	): asserts executionData is NonNullable<IRunExecutionData['executionData']> {
-		if (!executionData) {
-			throw new UnexpectedError('Failed to run workflow due to missing execution data', {
-				extra: {
-					workflowId: workflow.id,
-					executionId: this.additionalData.executionId,
-					mode: this.mode,
-				},
-			});
-		}
-	}
-
 	/**
 	 * Handles executions that have been waiting by
 	 * 1. unsetting the `waitTill`
@@ -1354,7 +1340,12 @@ export class WorkflowExecute {
 		if (this.runExecutionData.waitTill) {
 			this.runExecutionData.waitTill = undefined;
 
-			this.assertExecutionDataExists(this.runExecutionData.executionData, workflow);
+			assertExecutionDataExists(
+				this.runExecutionData.executionData,
+				workflow,
+				this.additionalData,
+				this.mode,
+			);
 			this.runExecutionData.executionData.nodeExecutionStack[0].node.disabled = true;
 
 			const lastNodeExecuted = this.runExecutionData.resultData.lastNodeExecuted as string;
@@ -1363,7 +1354,12 @@ export class WorkflowExecute {
 	}
 
 	private checkForWorkflowIssues(workflow: Workflow): void {
-		this.assertExecutionDataExists(this.runExecutionData.executionData, workflow);
+		assertExecutionDataExists(
+			this.runExecutionData.executionData,
+			workflow,
+			this.additionalData,
+			this.mode,
+		);
 		// Node execution stack will be empty for an execution containing only Chat
 		// Trigger.
 		const startNode = this.runExecutionData.executionData.nodeExecutionStack.at(0)?.node.name;
@@ -1487,6 +1483,14 @@ export class WorkflowExecute {
 			// eslint-disable-next-line complexity
 			const returnPromise = (async () => {
 				try {
+					// Establish the execution context
+					await establishExecutionContext(
+						workflow,
+						this.runExecutionData,
+						this.additionalData,
+						this.mode,
+					);
+
 					if (!this.additionalData.restartExecutionId) {
 						await hooks.runHook('workflowExecuteBefore', [workflow, this.runExecutionData]);
 					}
diff --git a/packages/core/src/utils/__tests__/assertions.test.ts b/packages/core/src/utils/__tests__/assertions.test.ts
new file mode 100644
index 00000000000..7164dceac26
--- /dev/null
+++ b/packages/core/src/utils/__tests__/assertions.test.ts
@@ -0,0 +1,109 @@
+import { mock } from 'jest-mock-extended';
+import type { IRunExecutionData, IWorkflowExecuteAdditionalData, Workflow } from 'n8n-workflow';
+import { UnexpectedError } from 'n8n-workflow';
+
+import { assertExecutionDataExists } from '../assertions';
+
+describe('assertExecutionDataExists', () => {
+	const mockWorkflow = mock<Workflow>({ id: 'test-workflow-123' });
+	const mockAdditionalData = mock<IWorkflowExecuteAdditionalData>({
+		executionId: 'test-execution-456',
+	});
+	const mode = 'manual';
+
+	describe('when executionData is valid', () => {
+		it('should not throw when executionData exists', () => {
+			const validExecutionData = {
+				contextData: {},
+				nodeExecutionStack: [],
+				metadata: {},
+				waitingExecution: {},
+				waitingExecutionSource: {},
+			};
+
+			expect(() =>
+				assertExecutionDataExists(validExecutionData, mockWorkflow, mockAdditionalData, mode),
+			).not.toThrow();
+		});
+
+		it('should not throw when executionData has minimal properties', () => {
+			const minimalExecutionData = {
+				nodeExecutionStack: [],
+			};
+
+			expect(() =>
+				assertExecutionDataExists(
+					minimalExecutionData as unknown as IRunExecutionData['executionData'],
+					mockWorkflow,
+					mockAdditionalData,
+					mode,
+				),
+			).not.toThrow();
+		});
+	});
+
+	describe('when executionData is missing', () => {
+		it('should throw UnexpectedError when executionData is undefined', () => {
+			expect(() =>
+				assertExecutionDataExists(undefined, mockWorkflow, mockAdditionalData, mode),
+			).toThrow(UnexpectedError);
+		});
+
+		it('should throw UnexpectedError when executionData is null', () => {
+			expect(() =>
+				assertExecutionDataExists(
+					null as unknown as IRunExecutionData['executionData'],
+					mockWorkflow,
+					mockAdditionalData,
+					mode,
+				),
+			).toThrow(UnexpectedError);
+		});
+
+		it('should throw error with correct message', () => {
+			expect(() =>
+				assertExecutionDataExists(undefined, mockWorkflow, mockAdditionalData, mode),
+			).toThrow(/missing execution data/i);
+		});
+
+		it('should include workflow metadata in error', () => {
+			try {
+				assertExecutionDataExists(undefined, mockWorkflow, mockAdditionalData, mode);
+				fail('Expected error to be thrown');
+			} catch (error) {
+				expect(error).toBeInstanceOf(UnexpectedError);
+				const unexpectedError = error as UnexpectedError;
+				expect(unexpectedError.extra).toEqual({
+					workflowId: 'test-workflow-123',
+					executionId: 'test-execution-456',
+					mode: 'manual',
+				});
+			}
+		});
+	});
+
+	describe('with different execution modes', () => {
+		it('should work with trigger mode', () => {
+			const validExecutionData = { nodeExecutionStack: [] };
+
+			expect(() =>
+				assertExecutionDataExists(
+					validExecutionData as unknown as IRunExecutionData['executionData'],
+					mockWorkflow,
+					mockAdditionalData,
+					'trigger',
+				),
+			).not.toThrow();
+		});
+
+		it('should include mode in error metadata', () => {
+			try {
+				assertExecutionDataExists(undefined, mockWorkflow, mockAdditionalData, 'webhook');
+				fail('Expected error to be thrown');
+			} catch (error) {
+				const unexpectedError = error as UnexpectedError;
+				expect(unexpectedError.extra?.mode).toBe('webhook');
+			}
+		});
+	});
+});
diff --git a/packages/core/src/utils/assertions.ts b/packages/core/src/utils/assertions.ts
new file mode 100644
index 00000000000..9110d0f797e
--- /dev/null
+++ b/packages/core/src/utils/assertions.ts
@@ -0,0 +1,24 @@
+import {
+	type IRunExecutionData,
+	type IWorkflowExecuteAdditionalData,
+	UnexpectedError,
+	type Workflow,
+	type WorkflowExecuteMode,
+} from 'n8n-workflow';
+
+export function assertExecutionDataExists(
+	executionData: IRunExecutionData['executionData'],
+	workflow: Workflow,
+	additionalData: IWorkflowExecuteAdditionalData,
+	mode: WorkflowExecuteMode,
+): asserts executionData is NonNullable<IRunExecutionData['executionData']> {
+	if (!executionData) {
+		throw new UnexpectedError('Failed to run workflow due to missing execution data', {
+			extra: {
+				workflowId: workflow.id,
+				executionId: additionalData.executionId,
+				mode,
+			},
+		});
+	}
+}
diff --git a/packages/workflow/src/execution-context.ts b/packages/workflow/src/execution-context.ts
index 862d6852b9f..ee9585ea7df 100644
--- a/packages/workflow/src/execution-context.ts
+++ b/packages/workflow/src/execution-context.ts
@@ -30,12 +30,33 @@ export const CredentialContextSchema = z
  */
 export type ICredentialContext = z.output<typeof CredentialContextSchema>;
 
+const WorkflowExecuteModeSchema = z.union([
+	z.literal('cli'),
+	z.literal('error'),
+	z.literal('integrated'),
+	z.literal('internal'),
+	z.literal('manual'),
+	z.literal('retry'),
+	z.literal('trigger'),
+	z.literal('webhook'),
+	z.literal('evaluation'),
+	z.literal('chat'),
+]);
+
+export type WorkflowExecuteModeValues = z.infer<typeof WorkflowExecuteModeSchema>;
+
 const ExecutionContextSchemaV1 = z.object({
 	version: z.literal(1),
 	/**
 	 * When the context was established (Unix timestamp in milliseconds)
 	 */
 	establishedAt: z.number(),
+
+	/**
+	 * The mode in which the workflow is being executed
+	 */
+	source: WorkflowExecuteModeSchema,
+
 	/**
 	 * Encrypted credential context for dynamic credential resolution
 	 * Always encrypted when stored, decrypted on-demand by credential resolver
diff --git a/packages/workflow/src/interfaces.ts b/packages/workflow/src/interfaces.ts
index 10ef7018a54..f0798f1ec2e 100644
--- a/packages/workflow/src/interfaces.ts
+++ b/packages/workflow/src/interfaces.ts
@@ -24,11 +24,16 @@ import type { NodeApiError } from './errors/node-api.error';
 import type { NodeOperationError } from './errors/node-operation.error';
 import type { WorkflowActivationError } from './errors/workflow-activation.error';
 import type { WorkflowOperationError } from './errors/workflow-operation.error';
+import type {
+	IExecutionContext,
+	WorkflowExecuteModeValues as WorkflowExecuteMode,
+} from './execution-context';
 import type { ExecutionStatus } from './execution-status';
 import type { Result } from './result';
 import type { Workflow } from './workflow';
 import type { EnvProviderState } from './workflow-data-proxy-env-provider';
-import type { IExecutionContext } from './execution-context';
+
+export type { WorkflowExecuteModeValues as WorkflowExecuteMode } from './execution-context';
 
 export interface IAdditionalCredentialOptions {
 	oauth2?: IOAuth2Options;
@@ -2723,18 +2728,6 @@ export interface IWorkflowExecuteAdditionalData {
 	): Promise<Result<T, E>>;
 }
 
-export type WorkflowExecuteMode =
-	| 'cli'
-	| 'error'
-	| 'integrated'
-	| 'internal'
-	| 'manual'
-	| 'retry'
-	| 'trigger'
-	| 'webhook'
-	| 'evaluation'
-	| 'chat';
-
 export type WorkflowActivateMode =
 	| 'init'
 	| 'create' // unused