diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/hooks/use-workflow-execution.ts b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/hooks/use-workflow-execution.ts
index 471cecd9b..f68d870d1 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/hooks/use-workflow-execution.ts
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/hooks/use-workflow-execution.ts
@@ -1661,11 +1661,16 @@ export function useWorkflowExecution() {
             },
 
             onExecutionError: (data) => {
-              if (data.error?.includes('Block not found in workflow')) {
+              const isWorkflowModified =
+                data.error?.includes('Block not found in workflow') ||
+                data.error?.includes('Upstream dependency not executed')
+
+              if (isWorkflowModified) {
                 clearLastExecutionSnapshot(workflowId)
                 addNotification({
-                  level: 'info',
-                  message: 'Workflow was modified. Run the workflow again to refresh.',
+                  level: 'error',
+                  message:
+                    'Workflow was modified. Run the workflow again to enable running from block.',
                   workflowId,
                 })
               } else {
diff --git a/apps/sim/executor/utils/run-from-block.test.ts b/apps/sim/executor/utils/run-from-block.test.ts
index 07e39c58d..528b44def 100644
--- a/apps/sim/executor/utils/run-from-block.test.ts
+++ b/apps/sim/executor/utils/run-from-block.test.ts
@@ -331,6 +331,24 @@ describe('validateRunFromBlock', () => {
     expect(result.error).toContain('Upstream dependency not executed')
   })
 
+  it('rejects blocks with unexecuted transitive upstream dependencies', () => {
+    // A → X → B → C, where X is new (not executed)
+    // Running from C should fail because X in upstream chain wasn't executed
+    const dag = createDAG([
+      createNode('A', [{ target: 'X' }]),
+      createNode('X', [{ target: 'B' }]),
+      createNode('B', [{ target: 'C' }]),
+      createNode('C'),
+    ])
+    const executedBlocks = new Set(['A', 'B', 'C']) // X was not executed (new block)
+
+    const result = validateRunFromBlock('C', dag, executedBlocks)
+
+    expect(result.valid).toBe(false)
+    expect(result.error).toContain('Upstream dependency not executed')
+    expect(result.error).toContain('X')
+  })
+
   it('allows blocks with no dependencies even if not previously executed', () => {
     // A and B are independent (no edges)
     const dag = createDAG([createNode('A'), createNode('B')])
diff --git a/apps/sim/executor/utils/run-from-block.ts b/apps/sim/executor/utils/run-from-block.ts
index 5813d52b5..dbe2e3fcd 100644
--- a/apps/sim/executor/utils/run-from-block.ts
+++ b/apps/sim/executor/utils/run-from-block.ts
@@ -169,15 +169,15 @@ export function validateRunFromBlock(
     if (node.metadata.isSentinel) {
       return { valid: false, error: 'Cannot run from sentinel node' }
     }
+  }
 
-    if (node.incomingEdges.size > 0) {
-      for (const sourceId of node.incomingEdges.keys()) {
-        if (!executedBlocks.has(sourceId)) {
-          return {
-            valid: false,
-            error: `Upstream dependency not executed: ${sourceId}`,
-          }
-        }
+  // Check that ALL upstream blocks were executed (transitive check)
+  const { upstreamSet } = computeExecutionSets(dag, blockId)
+  for (const upstreamId of upstreamSet) {
+    if (!executedBlocks.has(upstreamId)) {
+      return {
+        valid: false,
+        error: `Upstream dependency not executed: ${upstreamId}`,
       }
     }
   }