diff --git a/litellm/proxy/policy_engine/pipeline_executor.py b/litellm/proxy/policy_engine/pipeline_executor.py
index c1e2d76e7cd..ad93eb4b1b1 100644
--- a/litellm/proxy/policy_engine/pipeline_executor.py
+++ b/litellm/proxy/policy_engine/pipeline_executor.py
@@ -5,6 +5,7 @@ Runs guardrails sequentially per pipeline step definitions, handling
 pass/fail actions (allow, block, next, modify_response) and data forwarding.
 """
 
+import asyncio
 import time
 from typing import Any, List, Optional
 
@@ -72,6 +73,27 @@ class PipelineExecutor:
                 call_type=call_type,
             )
 
+            retries_attempted = 0
+            if outcome != "pass" and step.num_retries > 0:
+                for retry in range(step.num_retries):
+                    retries_attempted = retry + 1
+                    verbose_proxy_logger.debug(
+                        f"Pipeline '{policy_name}' step {i}: retrying guardrail "
+                        f"'{step.guardrail}' (attempt {retries_attempted}/{step.num_retries})"
+                    )
+                    await asyncio.sleep(0.1 * retries_attempted)
+                    outcome, modified_data, error_detail = (
+                        await PipelineExecutor._run_step(
+                            step=step,
+                            mode=mode,
+                            data=working_data,
+                            user_api_key_dict=user_api_key_dict,
+                            call_type=call_type,
+                        )
+                    )
+                    if outcome == "pass":
+                        break
+
             duration = time.perf_counter() - start_time
 
             action = step.on_pass if outcome == "pass" else step.on_fail
@@ -83,12 +105,13 @@ class PipelineExecutor:
                 modified_data=modified_data,
                 error_detail=error_detail,
                 duration_seconds=round(duration, 4),
+                retries_attempted=retries_attempted,
             )
             step_results.append(step_result)
 
             verbose_proxy_logger.debug(
                 f"Pipeline '{policy_name}' step {i}: guardrail={step.guardrail}, "
-                f"outcome={outcome}, action={action}"
+                f"outcome={outcome}, action={action}, retries={retries_attempted}"
             )
 
             # Forward modified data to next step if pass_data is True
diff --git a/litellm/types/proxy/policy_engine/pipeline_types.py b/litellm/types/proxy/policy_engine/pipeline_types.py
index 29d2e576000..9040204ac6d 100644
--- a/litellm/types/proxy/policy_engine/pipeline_types.py
+++ b/litellm/types/proxy/policy_engine/pipeline_types.py
@@ -38,6 +38,12 @@ class PipelineStep(BaseModel):
         default=None,
         description="Custom message for modify_response action.",
     )
+    num_retries: int = Field(
+        default=0,
+        ge=0,
+        le=10,
+        description="Number of times to retry the guardrail on failure before applying the on_fail action.",
+    )
 
     model_config = ConfigDict(extra="forbid")
 
@@ -86,6 +92,10 @@ class PipelineStepResult(BaseModel):
     modified_data: Optional[Dict[str, Any]] = None
     error_detail: Optional[str] = None
     duration_seconds: Optional[float] = None
+    retries_attempted: int = Field(
+        default=0,
+        description="Number of retries that were attempted before the final outcome.",
+    )
 
 
 class PipelineExecutionResult(BaseModel):
diff --git a/tests/test_litellm/proxy/policy_engine/test_pipeline_executor.py b/tests/test_litellm/proxy/policy_engine/test_pipeline_executor.py
index 226e88bea3e..769b1198bdc 100644
--- a/tests/test_litellm/proxy/policy_engine/test_pipeline_executor.py
+++ b/tests/test_litellm/proxy/policy_engine/test_pipeline_executor.py
@@ -46,6 +46,28 @@ class AlwaysFailGuardrail(CustomGuardrail):
         raise HTTPException(status_code=400, detail="Content policy violation")
 
 
+class FailThenPassGuardrail(CustomGuardrail):
+    """Mock guardrail that fails N times then passes."""
+
+    def __init__(self, guardrail_name: str, fail_count: int = 2):
+        super().__init__(
+            guardrail_name=guardrail_name,
+            event_hook="pre_call",
+            default_on=True,
+        )
+        self.calls = 0
+        self.fail_count = fail_count
+
+    def should_run_guardrail(self, data, event_type) -> bool:
+        return True
+
+    async def async_pre_call_hook(self, user_api_key_dict, cache, data, call_type):
+        self.calls += 1
+        if self.calls <= self.fail_count:
+            raise HTTPException(status_code=400, detail="Transient failure")
+        return None
+
+
 class AlwaysPassGuardrail(CustomGuardrail):
     """Mock guardrail that always passes."""
 
@@ -482,3 +504,220 @@ async def test_step_results_include_duration():
         assert result.step_results[0].duration_seconds >= 0
     finally:
         litellm.callbacks = original_callbacks
+
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Retry Tests
+# ─────────────────────────────────────────────────────────────────────────────
+
+
+@pytest.mark.skipif(HTTPException is None, reason="fastapi not installed")
+@pytest.mark.asyncio
+async def test_retry_succeeds_after_transient_failure():
+    """
+    Guardrail fails twice then passes. With num_retries=3, it should succeed.
+    """
+    guard = FailThenPassGuardrail(guardrail_name="flaky-guard", fail_count=2)
+
+    pipeline = GuardrailPipeline(
+        mode="pre_call",
+        steps=[
+            PipelineStep(
+                guardrail="flaky-guard",
+                on_fail="block",
+                on_pass="allow",
+                num_retries=3,
+            )
+        ],
+    )
+
+    original_callbacks = litellm.callbacks.copy()
+    litellm.callbacks = [guard]
+
+    try:
+        result = await PipelineExecutor.execute_steps(
+            steps=pipeline.steps,
+            mode=pipeline.mode,
+            data={"messages": [{"role": "user", "content": "test"}]},
+            user_api_key_dict=MagicMock(),
+            call_type="completion",
+            policy_name="retry-test",
+        )
+
+        assert guard.calls == 3  # 1 initial + 2 retries
+        assert result.terminal_action == "allow"
+        assert result.step_results[0].outcome == "pass"
+        assert result.step_results[0].retries_attempted == 2
+    finally:
+        litellm.callbacks = original_callbacks
+
+
+@pytest.mark.skipif(HTTPException is None, reason="fastapi not installed")
+@pytest.mark.asyncio
+async def test_retry_exhausted_still_fails():
+    """
+    Guardrail fails 4 times. With num_retries=2, it should exhaust retries and fail.
+    """
+    guard = FailThenPassGuardrail(guardrail_name="stubborn-guard", fail_count=4)
+
+    pipeline = GuardrailPipeline(
+        mode="pre_call",
+        steps=[
+            PipelineStep(
+                guardrail="stubborn-guard",
+                on_fail="block",
+                on_pass="allow",
+                num_retries=2,
+            )
+        ],
+    )
+
+    original_callbacks = litellm.callbacks.copy()
+    litellm.callbacks = [guard]
+
+    try:
+        result = await PipelineExecutor.execute_steps(
+            steps=pipeline.steps,
+            mode=pipeline.mode,
+            data={"messages": [{"role": "user", "content": "test"}]},
+            user_api_key_dict=MagicMock(),
+            call_type="completion",
+            policy_name="retry-test",
+        )
+
+        assert guard.calls == 3  # 1 initial + 2 retries
+        assert result.terminal_action == "block"
+        assert result.step_results[0].outcome == "fail"
+        assert result.step_results[0].retries_attempted == 2
+    finally:
+        litellm.callbacks = original_callbacks
+
+
+@pytest.mark.skipif(HTTPException is None, reason="fastapi not installed")
+@pytest.mark.asyncio
+async def test_no_retries_when_zero():
+    """
+    With num_retries=0 (default), guardrail failure triggers on_fail immediately.
+    """
+    guard = AlwaysFailGuardrail(guardrail_name="no-retry")
+
+    pipeline = GuardrailPipeline(
+        mode="pre_call",
+        steps=[
+            PipelineStep(
+                guardrail="no-retry",
+                on_fail="block",
+                on_pass="allow",
+                num_retries=0,
+            )
+        ],
+    )
+
+    original_callbacks = litellm.callbacks.copy()
+    litellm.callbacks = [guard]
+
+    try:
+        result = await PipelineExecutor.execute_steps(
+            steps=pipeline.steps,
+            mode=pipeline.mode,
+            data={"messages": [{"role": "user", "content": "test"}]},
+            user_api_key_dict=MagicMock(),
+            call_type="completion",
+            policy_name="retry-test",
+        )
+
+        assert guard.calls == 1
+        assert result.terminal_action == "block"
+        assert result.step_results[0].retries_attempted == 0
+    finally:
+        litellm.callbacks = original_callbacks
+
+
+@pytest.mark.asyncio
+async def test_no_retries_on_pass():
+    """
+    When a guardrail passes on the first try, no retries should be attempted.
+    """
+    guard = AlwaysPassGuardrail(guardrail_name="pass-guard")
+
+    pipeline = GuardrailPipeline(
+        mode="pre_call",
+        steps=[
+            PipelineStep(
+                guardrail="pass-guard",
+                on_fail="block",
+                on_pass="allow",
+                num_retries=3,
+            )
+        ],
+    )
+
+    original_callbacks = litellm.callbacks.copy()
+    litellm.callbacks = [guard]
+
+    try:
+        result = await PipelineExecutor.execute_steps(
+            steps=pipeline.steps,
+            mode=pipeline.mode,
+            data={"messages": [{"role": "user", "content": "test"}]},
+            user_api_key_dict=MagicMock(),
+            call_type="completion",
+            policy_name="retry-test",
+        )
+
+        assert guard.calls == 1
+        assert result.terminal_action == "allow"
+        assert result.step_results[0].retries_attempted == 0
+    finally:
+        litellm.callbacks = original_callbacks
+
+
+@pytest.mark.skipif(HTTPException is None, reason="fastapi not installed")
+@pytest.mark.asyncio
+async def test_retry_with_on_fail_next_still_retries():
+    """
+    Retries happen even when on_fail is 'next'. After retries exhausted, the
+    on_fail action is taken.
+    """
+    guard = AlwaysFailGuardrail(guardrail_name="retry-then-next")
+    fallback = AlwaysPassGuardrail(guardrail_name="fallback")
+
+    pipeline = GuardrailPipeline(
+        mode="pre_call",
+        steps=[
+            PipelineStep(
+                guardrail="retry-then-next",
+                on_fail="next",
+                on_pass="allow",
+                num_retries=1,
+            ),
+            PipelineStep(
+                guardrail="fallback",
+                on_fail="block",
+                on_pass="allow",
+            ),
+        ],
+    )
+
+    original_callbacks = litellm.callbacks.copy()
+    litellm.callbacks = [guard, fallback]
+
+    try:
+        result = await PipelineExecutor.execute_steps(
+            steps=pipeline.steps,
+            mode=pipeline.mode,
+            data={"messages": [{"role": "user", "content": "test"}]},
+            user_api_key_dict=MagicMock(),
+            call_type="completion",
+            policy_name="retry-test",
+        )
+
+        assert guard.calls == 2  # 1 initial + 1 retry
+        assert fallback.calls == 1
+        assert result.terminal_action == "allow"
+        assert result.step_results[0].outcome == "fail"
+        assert result.step_results[0].action_taken == "next"
+        assert result.step_results[0].retries_attempted == 1
+        assert result.step_results[1].outcome == "pass"
+    finally:
+        litellm.callbacks = original_callbacks
diff --git a/tests/test_litellm/types/proxy/policy_engine/test_pipeline_types.py b/tests/test_litellm/types/proxy/policy_engine/test_pipeline_types.py
index 21fecc015a3..e951a99d953 100644
--- a/tests/test_litellm/types/proxy/policy_engine/test_pipeline_types.py
+++ b/tests/test_litellm/types/proxy/policy_engine/test_pipeline_types.py
@@ -23,6 +23,7 @@ def test_pipeline_step_defaults():
     assert step.on_pass == "allow"
     assert step.pass_data is False
     assert step.modify_response_message is None
+    assert step.num_retries == 0
 
 
 def test_pipeline_step_valid_actions():
@@ -150,3 +151,42 @@ def test_pipeline_extra_fields_rejected():
             steps=[PipelineStep(guardrail="g")],
             unknown="value",
         )
+
+
+def test_pipeline_step_num_retries():
+    step = PipelineStep(guardrail="g", num_retries=3)
+    assert step.num_retries == 3
+
+
+def test_pipeline_step_num_retries_max():
+    step = PipelineStep(guardrail="g", num_retries=10)
+    assert step.num_retries == 10
+
+
+def test_pipeline_step_num_retries_negative_rejected():
+    with pytest.raises(ValidationError):
+        PipelineStep(guardrail="g", num_retries=-1)
+
+
+def test_pipeline_step_num_retries_exceeds_max_rejected():
+    with pytest.raises(ValidationError):
+        PipelineStep(guardrail="g", num_retries=11)
+
+
+def test_pipeline_step_result_retries_attempted():
+    result = PipelineStepResult(
+        guardrail_name="g1",
+        outcome="pass",
+        action_taken="allow",
+        retries_attempted=2,
+    )
+    assert result.retries_attempted == 2
+
+
+def test_pipeline_step_result_retries_attempted_default():
+    result = PipelineStepResult(
+        guardrail_name="g1",
+        outcome="pass",
+        action_taken="allow",
+    )
+    assert result.retries_attempted == 0
diff --git a/ui/litellm-dashboard/src/components/policies/pipeline_flow_builder.tsx b/ui/litellm-dashboard/src/components/policies/pipeline_flow_builder.tsx
index 89665774eee..48bb5bc84c5 100644
--- a/ui/litellm-dashboard/src/components/policies/pipeline_flow_builder.tsx
+++ b/ui/litellm-dashboard/src/components/policies/pipeline_flow_builder.tsx
@@ -1,5 +1,5 @@
 import React, { useState } from "react";
-import { Select, Typography, message, Spin } from "antd";
+import { Select, Typography, message, Spin, InputNumber } from "antd";
 import { Button, TextInput } from "@tremor/react";
 import { ArrowLeftIcon, PlusIcon } from "@heroicons/react/outline";
 import { DotsVerticalIcon } from "@heroicons/react/solid";
@@ -46,6 +46,7 @@ function createDefaultStep(): PipelineStep {
     on_fail: "block",
     pass_data: false,
     modify_response_message: null,
+    num_retries: 0,
   };
 }
 
@@ -92,6 +93,7 @@ function derivePipelineFromPolicy(policy: Policy | null | undefined): GuardrailP
         on_fail: "block" as const,
         pass_data: false,
         modify_response_message: null,
+        num_retries: 0,
       })),
     };
   }
@@ -154,6 +156,13 @@ const FailIcon: React.FC = () => (
   </svg>
 );
 
+const RetryIcon: React.FC = () => (
+  <svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="#f59e0b" strokeWidth="2.5" strokeLinecap="round" strokeLinejoin="round" style={{ flexShrink: 0 }}>
+    <polyline points="23 4 23 10 17 10" />
+    <path d="M20.49 15a9 9 0 1 1-2.12-9.36L23 10" />
+  </svg>
+);
+
 // ─────────────────────────────────────────────────────────────────────────────
 // Connector
 // ─────────────────────────────────────────────────────────────────────────────
@@ -348,6 +357,35 @@ const StepCard: React.FC<StepCardProps> = ({
           </div>
         )}
       </div>
+
+      {/* RETRIES section */}
+      <div style={{ borderTop: "1px solid #f0f0f0", padding: "14px 20px" }}>
+        <div className="flex items-center gap-2" style={{ marginBottom: 8 }}>
+          <RetryIcon />
+          <span style={{ fontSize: 13, fontWeight: 600, color: "#374151" }}>RETRIES</span>
+        </div>
+        <div className="flex items-center gap-3">
+          <div style={{ flex: 1 }}>
+            <label style={{ fontSize: 12, fontWeight: 500, color: "#6b7280", display: "block", marginBottom: 6 }}>
+              Retry on failure
+            </label>
+            <InputNumber
+              min={0}
+              max={10}
+              value={step.num_retries ?? 0}
+              onChange={(value) => onChange({ num_retries: value ?? 0 })}
+              style={{ width: "100%" }}
+            />
+          </div>
+          <div style={{ flex: 2 }}>
+            <span style={{ fontSize: 12, color: "#9ca3af", lineHeight: 1.4, display: "block", marginTop: 18 }}>
+              {(step.num_retries ?? 0) === 0
+                ? "No retries — on_fail action runs immediately."
+                : `Retry up to ${step.num_retries} time${(step.num_retries ?? 0) > 1 ? "s" : ""} before applying the on_fail action.`}
+            </span>
+          </div>
+        </div>
+      </div>
     </div>
   );
 };
@@ -565,14 +603,19 @@ export const PipelineInfoDisplay: React.FC<PipelineInfoDisplayProps> = ({ pipeli
           {/* Divider */}
           <div style={{ borderTop: "1px solid #f3f4f6", marginBottom: 10 }} />
 
-          {/* Pass / Fail */}
-          <div className="flex items-center gap-6" style={{ fontSize: 13, color: "#374151" }}>
+          {/* Pass / Fail / Retries */}
+          <div className="flex items-center gap-6" style={{ fontSize: 13, color: "#374151", flexWrap: "wrap" }}>
             <span className="flex items-center gap-1.5">
               <PassIcon /> Pass &#8594; {ACTION_LABELS[step.on_pass] || step.on_pass}
             </span>
             <span className="flex items-center gap-1.5">
               <FailIcon /> Fail &#8594; {ACTION_LABELS[step.on_fail] || step.on_fail}
             </span>
+            {(step.num_retries ?? 0) > 0 && (
+              <span className="flex items-center gap-1.5">
+                <RetryIcon /> {step.num_retries} {step.num_retries === 1 ? "retry" : "retries"}
+              </span>
+            )}
           </div>
         </div>
       </React.Fragment>
@@ -844,6 +887,11 @@ const PipelineTestPanel: React.FC<PipelineTestPanelProps> = ({
                         ({(step.duration_seconds * 1000).toFixed(0)}ms)
                       </span>
                     )}
+                    {(step.retries_attempted ?? 0) > 0 && (
+                      <span style={{ marginLeft: 8, color: "#f59e0b" }}>
+                        ({step.retries_attempted} {step.retries_attempted === 1 ? "retry" : "retries"})
+                      </span>
+                    )}
                   </div>
                   {step.error_detail && (
                     <div style={{ fontSize: 12, color: "#dc2626", marginTop: 4 }}>
diff --git a/ui/litellm-dashboard/src/components/policies/types.ts b/ui/litellm-dashboard/src/components/policies/types.ts
index 002ae17af0a..e1d84b23f88 100644
--- a/ui/litellm-dashboard/src/components/policies/types.ts
+++ b/ui/litellm-dashboard/src/components/policies/types.ts
@@ -26,6 +26,7 @@ export interface PipelineStep {
   on_pass: "allow" | "block" | "next" | "modify_response";
   pass_data?: boolean;
   modify_response_message?: string | null;
+  num_retries?: number;
 }
 
 export interface GuardrailPipeline {
@@ -99,6 +100,7 @@ export interface PipelineStepResult {
   modified_data: Record<string, any> | null;
   error_detail: string | null;
   duration_seconds: number | null;
+  retries_attempted?: number;
 }
 
 export interface PipelineTestResult {