diff --git a/src/renderer/components/WorkflowEditor.tsx b/src/renderer/components/WorkflowEditor.tsx
index 8ef13b6..25dff13 100644
--- a/src/renderer/components/WorkflowEditor.tsx
+++ b/src/renderer/components/WorkflowEditor.tsx
@@ -296,6 +296,7 @@ export function WorkflowEditor({
             onNodeRemove={handleNodeRemove}
             selectedEdgeId={selectedEdgeId}
             selectedNodeId={selectedNodeId}
+            validationIssues={issues}
             workflow={workflow}
           />
         </div>
diff --git a/src/renderer/components/workflow/ConditionEditor.tsx b/src/renderer/components/workflow/ConditionEditor.tsx
new file mode 100644
index 0000000..673f82b
--- /dev/null
+++ b/src/renderer/components/workflow/ConditionEditor.tsx
@@ -0,0 +1,285 @@
+import { useCallback } from 'react';
+import { Info, Plus, Trash2 } from 'lucide-react';
+
+import type { EdgeCondition, WorkflowConditionRule } from '@shared/domain/workflow';
+
+type ConditionType = 'none' | 'always' | 'property' | 'message-type' | 'expression';
+
+interface ConditionEditorProps {
+  condition: EdgeCondition | undefined;
+  onChange: (condition: EdgeCondition | undefined) => void;
+  disabled?: boolean;
+}
+
+const OPERATOR_OPTIONS: { value: WorkflowConditionRule['operator']; label: string }[] = [
+  { value: 'equals', label: '=' },
+  { value: 'not-equals', label: '≠' },
+  { value: 'contains', label: 'contains' },
+  { value: 'gt', label: '>' },
+  { value: 'lt', label: '<' },
+  { value: 'regex', label: 'matches regex' },
+];
+
+const inputClasses =
+  'w-full rounded-lg border border-[var(--color-border)] bg-[var(--color-surface-1)] px-3 py-1.5 text-[12px] text-[var(--color-text-primary)] placeholder-[var(--color-text-muted)] outline-none transition focus:border-[var(--color-accent)]/50 disabled:cursor-not-allowed disabled:opacity-50';
+
+const selectClasses =
+  'w-full rounded-lg border border-[var(--color-border)] bg-[var(--color-surface-1)] px-3 py-1.5 text-[12px] text-[var(--color-text-primary)] outline-none transition focus:border-[var(--color-accent)]/50 disabled:cursor-not-allowed disabled:opacity-50';
+
+function resolveConditionType(condition: EdgeCondition | undefined): ConditionType {
+  if (!condition) return 'none';
+  return condition.type;
+}
+
+function emptyRule(): WorkflowConditionRule {
+  return { propertyPath: '', operator: 'equals', value: '' };
+}
+
+function defaultConditionForType(type: ConditionType): EdgeCondition | undefined {
+  switch (type) {
+    case 'none':
+      return undefined;
+    case 'always':
+      return { type: 'always' };
+    case 'property':
+      return { type: 'property', combinator: 'and', rules: [emptyRule()] };
+    case 'message-type':
+      return { type: 'message-type', typeName: '' };
+    case 'expression':
+      return { type: 'expression', expression: '' };
+  }
+}
+
+/* ── Property rules editor ─────────────────────────────────── */
+
+function PropertyRuleRow({
+  rule,
+  index,
+  disabled,
+  onRuleChange,
+  onRemove,
+  canRemove,
+}: {
+  rule: WorkflowConditionRule;
+  index: number;
+  disabled?: boolean;
+  onRuleChange: (index: number, patch: Partial<WorkflowConditionRule>) => void;
+  onRemove: (index: number) => void;
+  canRemove: boolean;
+}) {
+  return (
+    <div className="flex items-center gap-1.5">
+      <input
+        className={inputClasses}
+        disabled={disabled}
+        onChange={(e) => onRuleChange(index, { propertyPath: e.target.value })}
+        placeholder="property.path"
+        style={{ flex: 2 }}
+        value={rule.propertyPath}
+      />
+      <select
+        className={selectClasses}
+        disabled={disabled}
+        onChange={(e) =>
+          onRuleChange(index, { operator: e.target.value as WorkflowConditionRule['operator'] })
+        }
+        style={{ flex: 1.2 }}
+        value={rule.operator}
+      >
+        {OPERATOR_OPTIONS.map((op) => (
+          <option key={op.value} value={op.value}>
+            {op.label}
+          </option>
+        ))}
+      </select>
+      <input
+        className={inputClasses}
+        disabled={disabled}
+        onChange={(e) => onRuleChange(index, { value: e.target.value })}
+        placeholder="value"
+        style={{ flex: 2 }}
+        value={rule.value}
+      />
+      {canRemove && (
+        <button
+          className="flex size-6 shrink-0 items-center justify-center rounded text-[var(--color-text-muted)] transition hover:bg-[var(--color-status-error)]/10 hover:text-[var(--color-status-error)] disabled:pointer-events-none disabled:opacity-50"
+          disabled={disabled}
+          onClick={() => onRemove(index)}
+          title="Remove rule"
+          type="button"
+        >
+          <Trash2 className="size-3" />
+        </button>
+      )}
+    </div>
+  );
+}
+
+function PropertyRulesEditor({
+  condition,
+  disabled,
+  onChange,
+}: {
+  condition: Extract<EdgeCondition, { type: 'property' }>;
+  disabled?: boolean;
+  onChange: (condition: EdgeCondition) => void;
+}) {
+  const rules = condition.rules;
+
+  const handleRuleChange = useCallback(
+    (index: number, patch: Partial<WorkflowConditionRule>) => {
+      const updated = rules.map((r, i) => (i === index ? { ...r, ...patch } : r));
+      onChange({ ...condition, rules: updated });
+    },
+    [rules, condition, onChange],
+  );
+
+  const handleRemoveRule = useCallback(
+    (index: number) => {
+      onChange({ ...condition, rules: rules.filter((_, i) => i !== index) });
+    },
+    [rules, condition, onChange],
+  );
+
+  const handleAddRule = useCallback(() => {
+    onChange({ ...condition, rules: [...rules, emptyRule()] });
+  }, [rules, condition, onChange]);
+
+  const handleCombinatorChange = useCallback(
+    (combinator: 'and' | 'or') => {
+      onChange({ ...condition, combinator });
+    },
+    [condition, onChange],
+  );
+
+  return (
+    <div className="space-y-2">
+      {rules.length >= 2 && (
+        <div className="flex items-center gap-2">
+          <span className="text-[11px] text-[var(--color-text-muted)]">Combine</span>
+          <div className="flex rounded-lg border border-[var(--color-border)] bg-[var(--color-surface-1)]">
+            <button
+              className={`px-2.5 py-1 text-[11px] font-medium transition ${
+                (condition.combinator ?? 'and') === 'and'
+                  ? 'bg-[var(--color-accent)]/20 text-[var(--color-accent)]'
+                  : 'text-[var(--color-text-muted)] hover:text-[var(--color-text-secondary)]'
+              }`}
+              disabled={disabled}
+              onClick={() => handleCombinatorChange('and')}
+              type="button"
+            >
+              AND
+            </button>
+            <button
+              className={`px-2.5 py-1 text-[11px] font-medium transition ${
+                condition.combinator === 'or'
+                  ? 'bg-[var(--color-accent)]/20 text-[var(--color-accent)]'
+                  : 'text-[var(--color-text-muted)] hover:text-[var(--color-text-secondary)]'
+              }`}
+              disabled={disabled}
+              onClick={() => handleCombinatorChange('or')}
+              type="button"
+            >
+              OR
+            </button>
+          </div>
+        </div>
+      )}
+
+      {rules.map((rule, i) => (
+        <PropertyRuleRow
+          canRemove={rules.length > 1}
+          disabled={disabled}
+          index={i}
+          key={i}
+          onRemove={handleRemoveRule}
+          onRuleChange={handleRuleChange}
+          rule={rule}
+        />
+      ))}
+
+      <button
+        className="flex items-center gap-1 rounded-lg px-2 py-1 text-[11px] text-[var(--color-accent)] transition hover:bg-[var(--color-accent)]/10 disabled:pointer-events-none disabled:opacity-50"
+        disabled={disabled}
+        onClick={handleAddRule}
+        type="button"
+      >
+        <Plus className="size-3" />
+        Add Rule
+      </button>
+    </div>
+  );
+}
+
+/* ── Main condition editor ─────────────────────────────────── */
+
+export function ConditionEditor({ condition, onChange, disabled }: ConditionEditorProps) {
+  const currentType = resolveConditionType(condition);
+
+  const handleTypeChange = useCallback(
+    (type: ConditionType) => {
+      onChange(defaultConditionForType(type));
+    },
+    [onChange],
+  );
+
+  return (
+    <div className="space-y-2.5">
+      <label className="block space-y-1.5">
+        <span className="text-[12px] font-medium text-[var(--color-text-secondary)]">
+          Condition
+        </span>
+        <select
+          className={selectClasses}
+          disabled={disabled}
+          onChange={(e) => handleTypeChange(e.target.value as ConditionType)}
+          value={currentType}
+        >
+          <option value="none">None</option>
+          <option value="always">Always</option>
+          <option value="property">Property Rule</option>
+          <option value="message-type">Message Type</option>
+          <option value="expression">Expression</option>
+        </select>
+      </label>
+
+      {condition?.type === 'property' && (
+        <PropertyRulesEditor condition={condition} disabled={disabled} onChange={onChange} />
+      )}
+
+      {condition?.type === 'message-type' && (
+        <label className="block space-y-1.5">
+          <span className="text-[11px] text-[var(--color-text-muted)]">Type Name</span>
+          <input
+            className={inputClasses}
+            disabled={disabled}
+            onChange={(e) => onChange({ ...condition, typeName: e.target.value })}
+            placeholder="e.g. ApprovalResponse"
+            value={condition.typeName}
+          />
+        </label>
+      )}
+
+      {condition?.type === 'expression' && (
+        <div className="space-y-1.5">
+          <label className="block space-y-1.5">
+            <span className="text-[11px] text-[var(--color-text-muted)]">Expression</span>
+            <input
+              className={`${inputClasses} font-mono`}
+              disabled={disabled}
+              onChange={(e) => onChange({ ...condition, expression: e.target.value })}
+              placeholder='e.g. result.status == "done"'
+              value={condition.expression}
+            />
+          </label>
+          <div className="flex items-start gap-1.5 rounded-lg border border-[var(--color-border)] bg-[var(--color-surface-2)] px-2.5 py-2">
+            <Info className="mt-0.5 size-3 shrink-0 text-[var(--color-text-muted)]" />
+            <span className="text-[11px] leading-relaxed text-[var(--color-text-muted)]">
+              Supported: ==, !=, &gt;, &lt;, contains, matches. Combine with &amp;&amp; or ||
+            </span>
+          </div>
+        </div>
+      )}
+    </div>
+  );
+}
diff --git a/src/renderer/components/workflow/WorkflowGraphCanvas.tsx b/src/renderer/components/workflow/WorkflowGraphCanvas.tsx
index dce494b..8e679f3 100644
--- a/src/renderer/components/workflow/WorkflowGraphCanvas.tsx
+++ b/src/renderer/components/workflow/WorkflowGraphCanvas.tsx
@@ -33,6 +33,7 @@ import {
 } from '@renderer/lib/workflowGraph';
 
 import { workflowNodeTypes } from './WorkflowGraphNodes';
+import { workflowEdgeTypes } from './WorkflowGraphEdges';
 
 interface WorkflowGraphCanvasProps {
   workflow: WorkflowDefinition;
@@ -197,6 +198,7 @@ function WorkflowGraphCanvasInner({
         onEdgeClick={handleEdgeClick}
         onPaneClick={handlePaneClick}
         nodeTypes={workflowNodeTypes}
+        edgeTypes={workflowEdgeTypes}
         fitView
         fitViewOptions={{ padding: 0.3 }}
         minZoom={0.3}
diff --git a/src/renderer/components/workflow/WorkflowGraphEdges.tsx b/src/renderer/components/workflow/WorkflowGraphEdges.tsx
new file mode 100644
index 0000000..13b5f4f
--- /dev/null
+++ b/src/renderer/components/workflow/WorkflowGraphEdges.tsx
@@ -0,0 +1,14 @@
+import { BaseEdge, type EdgeProps } from '@xyflow/react';
+
+function SelfLoopEdge({ id, sourceX, sourceY, style, markerEnd }: EdgeProps) {
+  const loopHeight = 60;
+  const loopWidth = 40;
+
+  const path = `M ${sourceX} ${sourceY} C ${sourceX + loopWidth} ${sourceY - loopHeight}, ${sourceX - loopWidth} ${sourceY - loopHeight}, ${sourceX} ${sourceY}`;
+
+  return <BaseEdge id={id} path={path} style={style} markerEnd={markerEnd} />;
+}
+
+export const workflowEdgeTypes = {
+  selfLoop: SelfLoopEdge,
+} as const;
diff --git a/src/renderer/components/workflow/WorkflowGraphInspector.tsx b/src/renderer/components/workflow/WorkflowGraphInspector.tsx
index 535911e..fddc8b2 100644
--- a/src/renderer/components/workflow/WorkflowGraphInspector.tsx
+++ b/src/renderer/components/workflow/WorkflowGraphInspector.tsx
@@ -1,4 +1,5 @@
-import { Bot, Code, FunctionSquare, GitBranch, Info, Radio, Trash2 } from 'lucide-react';
+import { useCallback } from 'react';
+import { AlertCircle, Bot, Code, FunctionSquare, GitBranch, Info, Radio, Trash2 } from 'lucide-react';
 
 import {
   findModel,
@@ -7,19 +8,23 @@ import {
   type ModelDefinition,
 } from '@shared/domain/models';
 import type {
+  EdgeCondition,
   WorkflowDefinition,
   WorkflowEdge,
   WorkflowNode,
   WorkflowNodeConfig,
+  WorkflowValidationIssue,
   AgentNodeConfig,
 } from '@shared/domain/workflow';
 import { ModelSelect, ReasoningEffortSelect } from '@renderer/components/AgentConfigFields';
+import { ConditionEditor } from '@renderer/components/workflow/ConditionEditor';
 
 interface WorkflowGraphInspectorProps {
   availableModels: ReadonlyArray<ModelDefinition>;
   workflow: WorkflowDefinition;
   selectedNodeId: string | null;
   selectedEdgeId: string | null;
+  validationIssues?: WorkflowValidationIssue[];
   onNodeChange: (nodeId: string, patch: Partial<WorkflowNode>) => void;
   onNodeConfigChange: (nodeId: string, config: WorkflowNodeConfig) => void;
   onNodeRemove: (nodeId: string) => void;
@@ -238,13 +243,25 @@ function PlaceholderNodeInspector({
 
 function EdgeInspector({
   edge,
+  validationIssues,
   onEdgeChange,
   onEdgeRemove,
 }: {
   edge: WorkflowEdge;
+  validationIssues?: WorkflowValidationIssue[];
   onEdgeChange: (edgeId: string, patch: Partial<WorkflowEdge>) => void;
   onEdgeRemove: (edgeId: string) => void;
 }) {
+  const isFanIn = edge.kind === 'fan-in';
+  const edgeIssues = validationIssues?.filter((i) => i.edgeId === edge.id) ?? [];
+
+  const handleConditionChange = useCallback(
+    (condition: EdgeCondition | undefined) => {
+      onEdgeChange(edge.id, { condition });
+    },
+    [edge.id, onEdgeChange],
+  );
+
   return (
     <div className="space-y-4">
       <div className="flex items-center justify-between">
@@ -272,12 +289,83 @@ function EdgeInspector({
         </select>
       </label>
 
+      {/* Loop controls */}
+      <div className="space-y-2.5">
+        <label className="flex items-center justify-between">
+          <span className="text-[12px] font-medium text-[var(--color-text-secondary)]">
+            Loop Edge
+          </span>
+          <input
+            checked={edge.isLoop === true}
+            className="size-4 accent-[var(--color-accent)]"
+            onChange={(e) => {
+              if (e.target.checked) {
+                onEdgeChange(edge.id, { isLoop: true, maxIterations: edge.maxIterations ?? 10 });
+              } else {
+                onEdgeChange(edge.id, { isLoop: undefined, maxIterations: undefined });
+              }
+            }}
+            type="checkbox"
+          />
+        </label>
+        {edge.isLoop && (
+          <label className="block space-y-1.5">
+            <span className="text-[11px] text-[var(--color-text-muted)]">Max Iterations</span>
+            <input
+              className="w-full rounded-lg border border-[var(--color-border)] bg-[var(--color-surface-1)] px-3 py-1.5 text-[12px] text-[var(--color-text-primary)] outline-none transition focus:border-[var(--color-accent)]/50"
+              min={1}
+              onChange={(e) => {
+                const raw = parseInt(e.target.value, 10);
+                onEdgeChange(edge.id, {
+                  maxIterations: Number.isNaN(raw) ? undefined : Math.max(1, raw),
+                });
+              }}
+              type="number"
+              value={edge.maxIterations ?? 10}
+            />
+          </label>
+        )}
+      </div>
+
+      {/* Condition editor */}
+      <div className="space-y-1.5">
+        <ConditionEditor
+          condition={edge.condition}
+          disabled={isFanIn}
+          onChange={handleConditionChange}
+        />
+        {isFanIn && (
+          <p className="text-[11px] text-[var(--color-text-muted)]">
+            Fan-in edges cannot have conditions
+          </p>
+        )}
+      </div>
+
       <InputField
         label="Label"
         onChange={(v) => onEdgeChange(edge.id, { label: v || undefined })}
         placeholder="Optional edge label"
         value={edge.label ?? ''}
       />
+
+      {/* Validation issues for this edge */}
+      {edgeIssues.length > 0 && (
+        <div className="space-y-1">
+          {edgeIssues.map((issue, i) => (
+            <div
+              className={`flex items-start gap-1.5 rounded-lg px-2.5 py-1.5 text-[11px] ${
+                issue.level === 'error'
+                  ? 'bg-[var(--color-status-error)]/10 text-[var(--color-status-error)]'
+                  : 'bg-[var(--color-status-warning)]/10 text-[var(--color-status-warning)]'
+              }`}
+              key={`${issue.field ?? 'v'}-${i}`}
+            >
+              <AlertCircle className="mt-0.5 size-3 shrink-0" />
+              <span>{issue.message}</span>
+            </div>
+          ))}
+        </div>
+      )}
     </div>
   );
 }
@@ -289,6 +377,7 @@ export function WorkflowGraphInspector({
   workflow,
   selectedNodeId,
   selectedEdgeId,
+  validationIssues,
   onNodeChange,
   onNodeConfigChange,
   onNodeRemove,
@@ -305,7 +394,12 @@ export function WorkflowGraphInspector({
   if (selectedEdge) {
     return (
       <div className="p-4">
-        <EdgeInspector edge={selectedEdge} onEdgeChange={onEdgeChange} onEdgeRemove={onEdgeRemove} />
+        <EdgeInspector
+          edge={selectedEdge}
+          onEdgeChange={onEdgeChange}
+          onEdgeRemove={onEdgeRemove}
+          validationIssues={validationIssues}
+        />
       </div>
     );
   }
diff --git a/src/renderer/lib/workflowGraph.ts b/src/renderer/lib/workflowGraph.ts
index 4d4da28..6059f7b 100644
--- a/src/renderer/lib/workflowGraph.ts
+++ b/src/renderer/lib/workflowGraph.ts
@@ -94,19 +94,42 @@ const EDGE_DASH: Record<WorkflowEdgeKind, string | undefined> = {
   'fan-in': '2 2',
 };
 
+const LOOP_EDGE_COLOR = { stroke: '#c084fc', markerColor: '#c084fc' };
+const LOOP_EDGE_DASH = '8 4';
+
+function buildEdgeLabel(edge: WfEdge): string | undefined {
+  const parts: string[] = [];
+
+  if (edge.condition && edge.condition.type !== 'always') {
+    parts.push('⚡');
+  }
+
+  if (edge.label) {
+    parts.push(edge.label);
+  }
+
+  if (edge.isLoop && edge.maxIterations) {
+    parts.push(`🔁 ×${edge.maxIterations}`);
+  }
+
+  return parts.length > 0 ? parts.join(' ') : undefined;
+}
+
 export function toCanvasEdges(graph: WorkflowGraph): Edge[] {
   return graph.edges.map((edge) => {
-    const color = EDGE_COLORS[edge.kind] ?? EDGE_COLORS.direct;
-    const dashArray = EDGE_DASH[edge.kind];
+    const isLoop = edge.isLoop === true;
+    const isSelfLoop = edge.source === edge.target;
+    const color = isLoop ? LOOP_EDGE_COLOR : (EDGE_COLORS[edge.kind] ?? EDGE_COLORS.direct);
+    const dashArray = isLoop ? LOOP_EDGE_DASH : EDGE_DASH[edge.kind];
 
     return {
       id: edge.id,
       source: edge.source,
       target: edge.target,
-      type: 'default',
-      animated: edge.kind === 'fan-out',
+      type: isSelfLoop ? 'selfLoop' : 'default',
+      animated: isLoop || edge.kind === 'fan-out',
       deletable: true,
-      label: edge.label,
+      label: buildEdgeLabel(edge),
       markerEnd: { type: MarkerType.ArrowClosed, width: 16, height: 16, color: color.markerColor },
       style: {
         stroke: color.stroke,
@@ -144,10 +167,6 @@ export function isWorkflowConnectionAllowed(
     return false;
   }
 
-  if (connection.source === connection.target) {
-    return false;
-  }
-
   const sourceNode = graph.nodes.find((n) => n.id === connection.source);
   const targetNode = graph.nodes.find((n) => n.id === connection.target);
   if (!sourceNode || !targetNode) {