diff --git a/skyvern-frontend/src/routes/workflows/types/workflowRunTypes.ts b/skyvern-frontend/src/routes/workflows/types/workflowRunTypes.ts
index 2ba020e8..6937ed4c 100644
--- a/skyvern-frontend/src/routes/workflows/types/workflowRunTypes.ts
+++ b/skyvern-frontend/src/routes/workflows/types/workflowRunTypes.ts
@@ -167,3 +167,33 @@ export function hasNavigationGoal(
 ): item is { navigation_goal: unknown } {
   return item !== null && typeof item === "object" && "navigation_goal" in item;
 }
+
+// Branch evaluation types for conditional blocks
+export type BranchEvaluation = {
+  branch_id: string;
+  branch_index: number;
+  criteria_type: "jinja2_template" | "prompt" | null;
+  original_expression: string | null;
+  rendered_expression: string | null;
+  result: boolean | null;
+  is_matched: boolean;
+  is_default: boolean;
+  next_block_label: string | null;
+  error: string | null;
+};
+
+export type ConditionalBlockOutput = {
+  evaluations?: Array<BranchEvaluation>;
+  matched_branch_index?: number | null;
+};
+
+export function hasEvaluations(
+  output: unknown,
+): output is ConditionalBlockOutput {
+  return (
+    output !== null &&
+    typeof output === "object" &&
+    "evaluations" in output &&
+    Array.isArray((output as ConditionalBlockOutput).evaluations)
+  );
+}
diff --git a/skyvern-frontend/src/routes/workflows/workflowRun/WorkflowRunTimelineBlockItem.tsx b/skyvern-frontend/src/routes/workflows/workflowRun/WorkflowRunTimelineBlockItem.tsx
index 815d72d3..600dead4 100644
--- a/skyvern-frontend/src/routes/workflows/workflowRun/WorkflowRunTimelineBlockItem.tsx
+++ b/skyvern-frontend/src/routes/workflows/workflowRun/WorkflowRunTimelineBlockItem.tsx
@@ -18,6 +18,7 @@ import {
   isObserverThought,
   isThoughtItem,
   isWorkflowRunBlock,
+  hasEvaluations,
   WorkflowRunBlock,
   WorkflowRunTimelineItem,
 } from "../types/workflowRunTypes";
@@ -180,29 +181,100 @@ function WorkflowRunTimelineBlockItem({
           <div className="text-xs text-slate-400">{block.description}</div>
         ) : null}
         {block.block_type === "conditional" && block.executed_branch_id && (
-          <div className="space-y-1 rounded bg-slate-elevation5 px-3 py-2 text-xs">
-            {block.executed_branch_expression !== null &&
-            block.executed_branch_expression !== undefined ? (
-              <div className="text-slate-300">
-                Condition{" "}
-                <code className="rounded bg-slate-elevation3 px-1.5 py-0.5 font-mono text-slate-200">
-                  {block.executed_branch_expression}
-                </code>{" "}
-                evaluated to{" "}
-                <span className="font-medium text-success">True</span>
+          <div className="space-y-2 rounded bg-slate-elevation5 px-3 py-2 text-xs">
+            {hasEvaluations(block.output) && block.output.evaluations ? (
+              // New format: show all branch evaluations
+              <div className="space-y-2">
+                {block.output.evaluations.map((evaluation, index) => (
+                  <div
+                    key={evaluation.branch_id || index}
+                    className={cn(
+                      "rounded border px-2 py-1.5",
+                      evaluation.is_matched
+                        ? "border-success/50 bg-success/10"
+                        : "border-slate-600 bg-slate-elevation3",
+                    )}
+                  >
+                    {evaluation.is_default ? (
+                      <div className="text-slate-300">
+                        <span className="font-medium">Default branch</span>
+                        {evaluation.is_matched && (
+                          <span className="ml-2 text-success">✓ Matched</span>
+                        )}
+                      </div>
+                    ) : (
+                      <div className="space-y-1">
+                        <div className="text-slate-400">
+                          <code className="rounded bg-slate-elevation1 px-1 py-0.5 font-mono text-slate-300">
+                            {evaluation.original_expression}
+                          </code>
+                        </div>
+                        {evaluation.rendered_expression &&
+                          evaluation.rendered_expression !==
+                            evaluation.original_expression && (
+                            <div className="text-slate-400">
+                              → rendered to{" "}
+                              <code className="rounded bg-slate-elevation1 px-1 py-0.5 font-mono text-slate-200">
+                                {evaluation.rendered_expression}
+                              </code>
+                            </div>
+                          )}
+                        <div className="flex items-center gap-2">
+                          <span className="text-slate-400">evaluated to</span>
+                          <span
+                            className={cn(
+                              "font-medium",
+                              evaluation.result
+                                ? "text-success"
+                                : "text-red-400",
+                            )}
+                          >
+                            {evaluation.result ? "True" : "False"}
+                          </span>
+                          {evaluation.is_matched && (
+                            <span className="text-success">✓ Matched</span>
+                          )}
+                        </div>
+                      </div>
+                    )}
+                    {evaluation.is_matched && evaluation.next_block_label && (
+                      <div className="mt-1 text-slate-400">
+                        → Executing next block:{" "}
+                        <span className="font-medium text-slate-300">
+                          {evaluation.next_block_label}
+                        </span>
+                      </div>
+                    )}
+                  </div>
+                ))}
               </div>
             ) : (
-              <div className="text-slate-300">
-                No conditions matched, executing default branch
-              </div>
-            )}
-            {block.executed_branch_next_block && (
-              <div className="text-slate-400">
-                → Executing next block:{" "}
-                <span className="font-medium text-slate-300">
-                  {block.executed_branch_next_block}
-                </span>
-              </div>
+              // Fallback: old format without evaluations array
+              <>
+                {block.executed_branch_expression !== null &&
+                block.executed_branch_expression !== undefined ? (
+                  <div className="text-slate-300">
+                    Condition{" "}
+                    <code className="rounded bg-slate-elevation3 px-1.5 py-0.5 font-mono text-slate-200">
+                      {block.executed_branch_expression}
+                    </code>{" "}
+                    evaluated to{" "}
+                    <span className="font-medium text-success">True</span>
+                  </div>
+                ) : (
+                  <div className="text-slate-300">
+                    No conditions matched, executing default branch
+                  </div>
+                )}
+                {block.executed_branch_next_block && (
+                  <div className="text-slate-400">
+                    → Executing next block:{" "}
+                    <span className="font-medium text-slate-300">
+                      {block.executed_branch_next_block}
+                    </span>
+                  </div>
+                )}
+              </>
             )}
           </div>
         )}