diff --git a/python/sglang/srt/disaggregation/prefill.py b/python/sglang/srt/disaggregation/prefill.py
index 17aa028e0..a71302833 100644
--- a/python/sglang/srt/disaggregation/prefill.py
+++ b/python/sglang/srt/disaggregation/prefill.py
@@ -19,7 +19,9 @@ Life cycle of a request in the prefill server
 
 from __future__ import annotations
 
+import hashlib
 import logging
+from array import array
 from collections import deque
 from http import HTTPStatus
 from typing import TYPE_CHECKING, List, Optional
@@ -37,6 +39,7 @@ from sglang.srt.disaggregation.utils import (
     ReqToMetadataIdxAllocator,
     TransferBackend,
     get_kv_class,
+    is_aborted,
     is_mla_backend,
     poll_and_all_reduce_attn_cp_tp_group,
     prepare_abort,
@@ -67,7 +70,17 @@ if TYPE_CHECKING:
 logger = logging.getLogger(__name__)
 
 
-def release_req_to_metadata_buffer(
+def should_force_retry(req: Req) -> bool:
+    """Test hook to force a request into optimistic prefill retry."""
+    retry_prob = envs.SGLANG_TEST_FORCE_OPTIMISTIC_PREFILL_RETRY_PROB.get()
+    if retry_prob <= 0 or req.time_stats.prefill_retry_count > 0 or req.is_retracted:
+        return False
+
+    digest = hashlib.sha256(str(req.rid).encode()).digest()
+    return int.from_bytes(digest[:8], "big") < retry_prob * 2**64
+
+
+def maybe_release_metadata_buffer(
     req: Req, allocator: ReqToMetadataIdxAllocator
 ) -> None:
     """
@@ -79,11 +92,7 @@ def release_req_to_metadata_buffer(
         req: The request object that may have a metadata_buffer_index allocated
         allocator: The ReqToMetadataIdxAllocator instance to free the index
     """
-    if (
-        hasattr(req, "metadata_buffer_index")
-        and req.metadata_buffer_index is not None
-        and req.metadata_buffer_index >= 0
-    ):
+    if req.metadata_buffer_index >= 0:
         allocator.free(req.metadata_buffer_index)
         req.metadata_buffer_index = -1
 
@@ -214,9 +223,11 @@ class PrefillBootstrapQueue:
                 )
         return kv_manager
 
-    def add(self, req: Req, num_kv_heads: int) -> None:
+    def create_sender(self, req: Req, num_kv_heads: int) -> bool:
+        """Create a KV sender for the request without enqueuing it.
+        Returns False if the request exceeds KV capacity."""
         if self._check_if_req_exceed_kv_capacity(req):
-            return
+            return False
 
         backend = (
             TransferBackend.FAKE
@@ -235,6 +246,42 @@ class PrefillBootstrapQueue:
             pp_rank=self.pp_rank,
         )
         self._process_req(req)
+        req.pending_bootstrap = True
+        return True
+
+    def ensure_metadata_buffer(self, req: Req) -> bool:
+        if req.metadata_buffer_index >= 0:
+            return True
+
+        if self.req_to_metadata_buffer_idx_allocator.available_size() == 0:
+            return False
+        req.metadata_buffer_index = self.req_to_metadata_buffer_idx_allocator.alloc()
+        assert req.metadata_buffer_index is not None
+        return True
+
+    def finalize_bootstrap(self, req: Req) -> bool:
+        """Initialize the sender after bootstrap completes.
+        Returns False if no metadata buffer is available (non-terminal)."""
+        assert req.pending_bootstrap, f"finalize_bootstrap is not idempotent"
+        if not self.ensure_metadata_buffer(req):
+            return False
+
+        req.time_stats.set_bootstrap_done_time()
+        num_kv_indices = len(req.origin_input_ids)
+
+        decode_prefix_len = req.disagg_kv_sender.pop_decode_prefix_len()
+        req.start_send_idx = decode_prefix_len
+        num_kv_indices_to_send = num_kv_indices - decode_prefix_len
+        num_pages = kv_to_page_num(
+            num_kv_indices_to_send, self.token_to_kv_pool.page_size
+        )
+        req.disagg_kv_sender.init(num_pages, req.metadata_buffer_index)
+        req.pending_bootstrap = False
+        return True
+
+    def add(self, req: Req, num_kv_heads: int) -> None:
+        if not self.create_sender(req, num_kv_heads):
+            return
         self.queue.append(req)
 
     def extend(self, reqs: List[Req], num_kv_heads: int) -> None:
@@ -291,54 +338,31 @@ class PrefillBootstrapQueue:
                 if req.rid not in rids_to_check:
                     continue
 
-            if poll == KVPoll.Bootstrapping:
-                continue
-            elif poll == KVPoll.Failed:
-                error_message = f"Prefill bootstrap failed for request rank={self.tp_rank} {req.rid=} {req.bootstrap_room=}"
-                try:
-                    req.disagg_kv_sender.failure_exception()
-                except Exception as e:
-                    error_message += f" with exception {e}"
-                logger.error(error_message)
-                req.time_stats.trace_ctx.abort(abort_info={"reason": error_message})
-                prepare_abort(
-                    req, error_message, status_code=HTTPStatus.INTERNAL_SERVER_ERROR
-                )
-                self.scheduler.output_streamer.stream_output([req], req.return_logprob)
+            if poll == KVPoll.Failed:
+                self.scheduler.handle_bootstrap_failure(req)
                 indices_to_remove.add(i)
                 failed_reqs.append(req)
-                if self.scheduler.metrics_reporter.enable_metrics:
-                    self.scheduler.metrics_collector.increment_bootstrap_failed_reqs()
-                if self.scheduler.enable_hicache_storage:
-                    # to release prefetch events associated with the request
-                    self.scheduler.tree_cache.release_aborted_request(req.rid)
-                continue
-
-            # KV.WaitingForInput - decode is ready to receive. initialize the kv sender
-            req.time_stats.set_bootstrap_done_time()
-            num_kv_indices = len(req.origin_input_ids)
-            if self.req_to_metadata_buffer_idx_allocator.available_size() == 0:
-                break
-
-            req.metadata_buffer_index = (
-                self.req_to_metadata_buffer_idx_allocator.alloc()
-            )
-            assert req.metadata_buffer_index is not None
-
-            # Cal number of pages to send
-            # if decode has a cached prefix, we need to send the delta indices
-            # otherwise, send the entire request
-            decode_prefix_len = req.disagg_kv_sender.pop_decode_prefix_len()
-            req.start_send_idx = decode_prefix_len
-            num_kv_indices_to_send = num_kv_indices - decode_prefix_len
-            num_pages = kv_to_page_num(
-                num_kv_indices_to_send, self.token_to_kv_pool.page_size
-            )
-            req.disagg_kv_sender.init(num_pages, req.metadata_buffer_index)
-
-            bootstrapped_reqs.append(req)
-            indices_to_remove.add(i)
-            req.time_stats.set_wait_queue_entry_time()
+            elif poll == KVPoll.Bootstrapping:
+                if (
+                    req.time_stats.prefill_retry_count
+                    < self.scheduler.server_args.optimistic_prefill_retries
+                    and not req.is_retracted  # engine paused
+                ):
+                    if not self.ensure_metadata_buffer(req):
+                        continue  # no more metadata buffer
+                    bootstrapped_reqs.append(req)
+                    indices_to_remove.add(i)
+                    req.time_stats.set_wait_queue_entry_time()
+            elif poll == KVPoll.WaitingForInput:
+                if not self.finalize_bootstrap(req):
+                    continue
+                bootstrapped_reqs.append(req)
+                indices_to_remove.add(i)
+                req.time_stats.set_wait_queue_entry_time()
+            else:
+                raise RuntimeError(
+                    f"Unexpected poll state {poll} for req {req.rid} in pop_bootstrapped"
+                )
 
         self.queue = [
             entry for i, entry in enumerate(self.queue) if i not in indices_to_remove
@@ -521,13 +545,50 @@ class SchedulerDisaggregationPrefillMixin:
                     v.tolist() for v in logits_output.next_token_token_ids_logprobs_val
                 ]
 
+        def advance_logprob_pt(i: int, req: Req) -> None:
+            nonlocal logprob_pt
+            if not req.return_logprob or extend_input_len_per_req is None:
+                return
+            extend_logprob_start_len = extend_logprob_start_len_per_req[i]
+            extend_input_len = extend_input_len_per_req[i]
+            if extend_logprob_start_len < extend_input_len:
+                logprob_pt += extend_input_len - extend_logprob_start_len
+
+        # Poll optimistic prefill requests in this batch.
+        # Note: In overlap scheduling, a chunked request that was still pending
+        # during process_prefill_chunk is not checked again here.
+        # If it becomes ready in the gap, we still retry the request to keep
+        # chunked-prefill state management simple.
+        optimistic_polls = {}
+        optimistic_reqs = [
+            (i, req)
+            for i, req in enumerate(batch.reqs)
+            if req.pending_bootstrap and req.inflight_middle_chunks <= 0
+        ]
+        if optimistic_reqs:
+            polls = poll_and_all_reduce_attn_cp_tp_group(
+                [req.disagg_kv_sender for _, req in optimistic_reqs],
+                self.attn_cp_cpu_group,
+                self.attn_tp_cpu_group,
+            )
+            optimistic_polls = {
+                idx: poll for (idx, _), poll in zip(optimistic_reqs, polls)
+            }
+
         for i, (req, next_token_id) in enumerate(
             zip(batch.reqs, next_token_ids, strict=True)
         ):
             if req.inflight_middle_chunks <= 0:
                 req.time_stats.set_prefill_finished_time()
 
-                # There is no output_ids for prefill
+                # For optimistic requests, check bootstrap before side effects
+                if i in optimistic_polls:
+                    if not self.handle_pending_bootstrap(
+                        req, optimistic_polls[i], defer_release=False
+                    ):
+                        advance_logprob_pt(i, req)
+                        continue
+
                 req.output_ids.append(next_token_id)
                 maybe_cache_unfinished_req(req, self.tree_cache)
                 self.disagg_prefill_inflight_queue.append(req)
@@ -558,12 +619,9 @@ class SchedulerDisaggregationPrefillMixin:
                 req.time_stats.set_prefill_transfer_queue_entry_time()
 
                 if req.grammar is not None:
-                    # FIXME: this try-except block is for handling unexpected xgrammar issue.
                     try:
                         req.grammar.accept_token(next_token_id)
                     except ValueError as e:
-                        # Grammar accept_token can raise ValueError if the token is not in the grammar.
-                        # This can happen if the grammar is not set correctly or the token is invalid.
                         error_message = f"Grammar accept_token failed for req {req.rid} with token {next_token_id}: {e}"
                         release_kv_cache(req, self.tree_cache)
                         prepare_abort(
@@ -576,11 +634,24 @@ class SchedulerDisaggregationPrefillMixin:
                 # being chunked reqs' prefill is not finished
                 req.inflight_middle_chunks -= 1
 
+                # Overlap deferred release for optimistic requests stopped in process_prefill_chunk
+                if req.pending_bootstrap:
+                    advance_logprob_pt(i, req)
+                    self.optimistic_release_and_requeue(req)
+                    req.time_stats.set_last_chunked_prefill_finish_time()
+                    continue
+
+                # Optimistic bootstrap can fail while this overlapped chunk is
+                # already running. Drop aborted chunks instead of sending KV.
+                if is_aborted(req):
+                    advance_logprob_pt(i, req)
+                    req.time_stats.set_last_chunked_prefill_finish_time()
+                    continue
+
                 if req.return_logprob:
                     extend_logprob_start_len = extend_logprob_start_len_per_req[i]
                     extend_input_len = extend_input_len_per_req[i]
                     if extend_logprob_start_len < extend_input_len:
-                        # Update input logprobs.
                         num_input_logprobs = extend_input_len - extend_logprob_start_len
                         self.batch_result_processor.logprob_result_processor.add_input_logprob_return_values(
                             i,
@@ -593,6 +664,9 @@ class SchedulerDisaggregationPrefillMixin:
                         logprob_pt += num_input_logprobs
 
                 if self.enable_overlap:
+                    assert (
+                        req.metadata_buffer_index >= 0
+                    ), f"Req {req.rid} does not have metadata buffer allocated"
                     self.send_kv_chunk(req, last_chunk=False, end_idx=req.tmp_end_idx)
                 req.time_stats.set_last_chunked_prefill_finish_time()
 
@@ -708,7 +782,7 @@ class SchedulerDisaggregationPrefillMixin:
         for req in done_reqs:
             req: Req
 
-            release_req_to_metadata_buffer(
+            maybe_release_metadata_buffer(
                 req, self.req_to_metadata_buffer_idx_allocator
             )
 
@@ -734,12 +808,77 @@ class SchedulerDisaggregationPrefillMixin:
 
         return transferred_rids
 
+    def handle_bootstrap_failure(self: Scheduler, req: Req) -> None:
+        error_message = (
+            f"Prefill bootstrap failed for request rank={self.ps.tp_rank} "
+            f"{req.rid=} {req.bootstrap_room=}"
+        )
+        try:
+            req.disagg_kv_sender.failure_exception()
+        except Exception as e:
+            error_message += f" with exception {e}"
+        logger.warning(error_message)
+        req.time_stats.trace_ctx.abort(abort_info={"reason": error_message})
+        if req.req_pool_idx is not None or self.tree_cache.supports_mamba():
+            release_kv_cache(req, self.tree_cache)
+        maybe_release_metadata_buffer(req, self.req_to_metadata_buffer_idx_allocator)
+        req.pending_bootstrap = False
+        prepare_abort(req, error_message, status_code=HTTPStatus.INTERNAL_SERVER_ERROR)
+        self.output_streamer.stream_output([req], req.return_logprob)
+        if self.metrics_reporter.enable_metrics:
+            self.metrics_collector.increment_bootstrap_failed_reqs()
+        if self.enable_hicache_storage:
+            self.tree_cache.release_aborted_request(req.rid)
+
+    def handle_pending_bootstrap(
+        self: Scheduler, req: Req, poll: KVPoll, defer_release: bool
+    ) -> bool:
+        """Return True when bootstrap is finalized and KV transfer can proceed."""
+        if poll == KVPoll.Failed:
+            self.handle_bootstrap_failure(req)
+            return False
+        elif poll == KVPoll.Bootstrapping:
+            if not defer_release:
+                self.optimistic_release_and_requeue(req)
+            return False
+        elif poll == KVPoll.WaitingForInput:
+            force_retry = should_force_retry(req)  # test hook
+            if force_retry:
+                if not defer_release:
+                    self.optimistic_release_and_requeue(req)
+                return False
+            # Metadata buffer was allocated in pop_bootstrapped before
+            # the request entered the waiting queue, so finalize should not fail.
+            assert self.disagg_prefill_bootstrap_queue.finalize_bootstrap(req)
+            return True
+        else:
+            raise RuntimeError(
+                f"Unexpected poll state {poll} for req {req.rid} in handle_pending_bootstrap"
+            )
+
+    def check_bootstrap(self: Scheduler, req: Req) -> bool:
+        """Check bootstrap status for an optimistic prefilled request.
+        Returns True if bootstrap is finished."""
+        if not req.pending_bootstrap:
+            return True
+        polls = poll_and_all_reduce_attn_cp_tp_group(
+            [req.disagg_kv_sender],
+            self.attn_cp_cpu_group,
+            self.attn_tp_cpu_group,
+        )
+        return self.handle_pending_bootstrap(
+            req, polls[0], defer_release=self.enable_overlap
+        )
+
     def process_prefill_chunk(self: Scheduler) -> None:
         chunked_req_to_exclude = set()
         if self.chunked_req:
             chunked_req_to_exclude.add(self.chunked_req)
             maybe_cache_unfinished_req(self.chunked_req, self.tree_cache, chunked=True)
-            if self.enable_overlap:
+
+            if not self.check_bootstrap(self.chunked_req):
+                self.chunked_req = None  # stop the current chunked prefill
+            elif self.enable_overlap:
                 # Delay KV transfer to process_batch_result_disagg_prefill when overlap is enabled to ensure results are resolved
                 self.chunked_req.tmp_end_idx = min(
                     len(self.chunked_req.fill_ids),
@@ -747,7 +886,9 @@ class SchedulerDisaggregationPrefillMixin:
                 )
             else:
                 self.send_kv_chunk(self.chunked_req)
-            self.running_batch.batch_is_full = False
+
+            if self.chunked_req is not None:
+                self.running_batch.batch_is_full = False
 
         if self.last_batch and self.last_batch.forward_mode.is_extend():
             if self.last_batch.chunked_req:
@@ -853,3 +994,34 @@ class SchedulerDisaggregationPrefillMixin:
             return
         req.disagg_kv_sender.send(page_indices, state_indices)
         req.start_send_idx = end_idx
+
+    def optimistic_release_and_requeue(self: Scheduler, req: Req) -> None:
+        """Release KV cache and requeue an optimistic prefill request."""
+        max_retries = self.server_args.optimistic_prefill_retries
+        maybe_cache_unfinished_req(req, self.tree_cache)
+        release_kv_cache(req, self.tree_cache)
+        req.reset_for_retract()
+        req.output_ids = array("q")
+        req.start_send_idx = 0
+        req.tmp_end_idx = -1
+        req.hidden_states_tensor = None
+        req.pending_bootstrap = True
+        req.time_stats.reset_prefill_retry_time()
+        if req.time_stats.prefill_retry_count >= max_retries:
+            logger.info(
+                f"Req {req.rid} exhausted optimistic prefill retries "
+                "falling back to bootstrap queue"
+            )
+            # Reset it so the next real bootstrap done can be recorded.
+            req.time_stats.bootstrap_done_time = 0.0
+            self.disagg_prefill_bootstrap_queue.queue.append(req)
+        else:
+            req.time_stats.prefill_retry_count += 1
+            logger.info(
+                f"Req {req.rid} optimistic prefill retry "
+                f"{req.time_stats.prefill_retry_count}/{max_retries}"
+            )
+            if self.metrics_reporter.enable_metrics:
+                self.metrics_collector.increment_prefill_retries(1)
+            req.time_stats.set_wait_queue_entry_time()
+            self.waiting_queue.insert(0, req)
diff --git a/python/sglang/srt/disaggregation/utils.py b/python/sglang/srt/disaggregation/utils.py
index bba4927ed..e1d7d9c8d 100644
--- a/python/sglang/srt/disaggregation/utils.py
+++ b/python/sglang/srt/disaggregation/utils.py
@@ -50,8 +50,22 @@ class DisaggregationMode(Enum):
 # Synchronization
 #########################
 
-# env var for testing failure, convert to float explicitly
-FAILURE_PROB = float(os.getenv("DISAGGREGATION_TEST_FAILURE_PROB", 0))
+
+def _get_failure_prob() -> float:
+    try:
+        return float(envs.SGLANG_TEST_DISAGG_FAILURE_PROB.get())
+    except Exception:
+        # fallback to legacy env var
+        return float(os.getenv("DISAGGREGATION_TEST_FAILURE_PROB", "0"))
+
+
+def _poll_with_failure_injection(pollers) -> List[int]:
+    if (failure_prob := _get_failure_prob()) > 0:
+        return [
+            int(KVPoll.Failed) if random.random() < failure_prob else int(poller.poll())
+            for poller in pollers
+        ]
+    return [int(poller.poll()) for poller in pollers]
 
 
 def _is_fake_transfer(req: Req, server_args: ServerArgs) -> bool:
@@ -87,13 +101,7 @@ def poll_and_all_reduce(
     server_args: Optional[ServerArgs] = None,
 ):
     # at a certain prob, the poll is failed to simulate failure
-    if FAILURE_PROB > 0:
-        polls = [
-            int(KVPoll.Failed) if random.random() < FAILURE_PROB else int(poller.poll())
-            for poller in pollers
-        ]
-    else:
-        polls = [int(poller.poll()) for poller in pollers]
+    polls = _poll_with_failure_injection(pollers)
 
     # Apply metadata gate on the decode requests to downgrade Success → Transferring for requests whose metadata hasn't landed.
     if (
@@ -141,7 +149,9 @@ def poll_and_all_reduce_with_staging(
         ):
             staging_handler.advance_scatter(decode_req)
 
-    raw_polls = [int(dr.kv_receiver.poll()) for dr in decode_reqs]
+    # allow test injection of failure probability at runtime
+    receivers = [dr.kv_receiver for dr in decode_reqs]
+    raw_polls = _poll_with_failure_injection(receivers)
     for i, decode_req in enumerate(decode_reqs):
         if raw_polls[i] == int(KVPoll.Success):
             if decode_req.kv_receiver.require_staging and not staging_handler.is_done(
@@ -689,3 +699,11 @@ def prepare_abort(req: Req, error_message: str, status_code=None):
         req.logprob.input_top_logprobs_idx = []
         req.logprob.input_token_ids_logprobs_val = []
         req.logprob.input_token_ids_logprobs_idx = []
+
+
+def is_aborted(req: Req) -> bool:
+    from sglang.srt.managers.schedule_batch import FINISH_ABORT
+
+    return isinstance(req.to_finish, FINISH_ABORT) or isinstance(
+        req.finished_reason, FINISH_ABORT
+    )
diff --git a/python/sglang/srt/environ.py b/python/sglang/srt/environ.py
index 4dc89fdc0..9c4321490 100644
--- a/python/sglang/srt/environ.py
+++ b/python/sglang/srt/environ.py
@@ -250,6 +250,7 @@ class Envs:
     SGLANG_OTLP_EXPORTER_MAX_EXPORT_BATCH_SIZE = EnvInt(64)
     SGLANG_NATIVE_MOVE_KV_CACHE = EnvBool(False)
     SGLANG_ENABLE_TP_MEMORY_INBALANCE_CHECK = EnvBool(True)
+    SGLANG_TEST_DISAGG_FAILURE_PROB = EnvFloat(0.0)
 
     # Scheduler: memory leak test
     SGLANG_TEST_RETRACT = EnvBool(False)
@@ -323,6 +324,7 @@ class Envs:
     # Test: pd-disaggregation
     SGLANG_TEST_PD_DISAGG_BACKEND = EnvStr("mooncake")
     SGLANG_TEST_PD_DISAGG_DEVICES = EnvStr(None)
+    SGLANG_TEST_FORCE_OPTIMISTIC_PREFILL_RETRY_PROB = EnvFloat(0.0)
 
     # Model Parallel
     SGLANG_USE_MESSAGE_QUEUE_BROADCASTER = EnvBool(True)
diff --git a/python/sglang/srt/managers/schedule_batch.py b/python/sglang/srt/managers/schedule_batch.py
index ed6a627c8..98948fb58 100755
--- a/python/sglang/srt/managers/schedule_batch.py
+++ b/python/sglang/srt/managers/schedule_batch.py
@@ -955,6 +955,9 @@ class Req(ReqDllmMixin):
         # We use `tmp_end_idx` to store the end index of the kv cache to send.
         self.tmp_end_idx: int = -1
         self.metadata_buffer_index: int = -1
+        # Used in overlap sequence to signal that an optimistic request should
+        # abort chunking. Set in create_sender, consumed in process_batch_result.
+        self.pending_bootstrap = False
 
         # For Matryoshka embeddings
         self.dimensions = dimensions
diff --git a/python/sglang/srt/managers/schedule_policy.py b/python/sglang/srt/managers/schedule_policy.py
index 5b0c41b3a..cb9857455 100644
--- a/python/sglang/srt/managers/schedule_policy.py
+++ b/python/sglang/srt/managers/schedule_policy.py
@@ -443,8 +443,10 @@ class PrefillAdder:
         self.preempt_list = []
         self.new_chunked_req = None
         self.log_hit_tokens = 0
+        self.reprocessed_log_hit_tokens = 0
         # TODO(lsyin): report the real input tokens excluding page alignment
         self.log_input_tokens = 0
+        self.reprocessed_log_input_tokens = 0
 
         if running_batch is not None:
             # Estimate the offset in the remaining token space
@@ -580,7 +582,11 @@ class PrefillAdder:
         return AddReqResult.CONTINUE
 
     def _update_prefill_budget(
-        self, prefix_len: int, extend_input_len: int, max_new_tokens: int
+        self,
+        prefix_len: int,
+        extend_input_len: int,
+        max_new_tokens: int,
+        retracted_stain: bool,
     ):
         # TODO(lsyin): check this workaround logic, which only ensures the prefill will not out of memory, and may be too conservative
         extend_input_len = self.ceil_paged_tokens(extend_input_len)
@@ -599,8 +605,13 @@ class PrefillAdder:
         elif self.rem_chunk_tokens is not None:
             self.rem_chunk_tokens -= extend_input_len
 
+        # reprocessed_log_* is a subset of log_*; metrics_reporter subtracts it
+        # when computing the first-attempt prefix cache hit rate.
         self.log_hit_tokens += prefix_len
         self.log_input_tokens += extend_input_len
+        if retracted_stain:
+            self.reprocessed_log_hit_tokens += prefix_len
+            self.reprocessed_log_input_tokens += extend_input_len
 
     def _get_dllm_remain_tokens(self) -> int:
         _rem_tokens = min(
@@ -628,7 +639,7 @@ class PrefillAdder:
 
         self.can_run_list.append(req)
 
-        self._update_prefill_budget(prefix_len, trunc_len, 0)
+        self._update_prefill_budget(prefix_len, trunc_len, 0, req.retracted_stain)
 
     def _req_inc_lock_ref(self, req: Req):
         result = self.tree_cache.inc_lock_ref(req.last_node)
@@ -654,7 +665,9 @@ class PrefillAdder:
             if not truncated
             else 0
         )
-        self._update_prefill_budget(0, req.extend_input_len, max_new_tokens)
+        self._update_prefill_budget(
+            0, req.extend_input_len, max_new_tokens, req.retracted_stain
+        )
 
         # Return based on remaining token availability
         return (
@@ -693,6 +706,7 @@ class PrefillAdder:
                 if not truncated
                 else 0
             ),
+            req.retracted_stain,
         )
 
         # Return if chunked prefill not finished
@@ -794,6 +808,7 @@ class PrefillAdder:
                 0,
                 req.extend_input_len,
                 min(req.sampling_params.max_new_tokens, CLIP_MAX_NEW_TOKENS),
+                req.retracted_stain,
             )
         else:
             if self.rem_chunk_tokens <= 0:
@@ -806,7 +821,7 @@ class PrefillAdder:
             req.fill_ids = req.fill_ids[:trunc_len]
             self.can_run_list.append(req)
             self.new_chunked_req = req
-            self._update_prefill_budget(0, trunc_len, 0)
+            self._update_prefill_budget(0, trunc_len, 0, req.retracted_stain)
 
         return self.budget_state()
 
@@ -926,6 +941,7 @@ class PrefillAdder:
                         req.sampling_params.max_new_tokens,
                         CLIP_MAX_NEW_TOKENS,
                     ),
+                    req.retracted_stain,
                 )
             else:
                 # Make sure at least one page is available
@@ -960,7 +976,9 @@ class PrefillAdder:
                 self.new_chunked_req = req
 
                 self._req_inc_lock_ref(req)
-                self._update_prefill_budget(prefix_len, trunc_len, 0)
+                self._update_prefill_budget(
+                    prefix_len, trunc_len, 0, req.retracted_stain
+                )
 
         return self.budget_state()
 
diff --git a/python/sglang/srt/managers/scheduler.py b/python/sglang/srt/managers/scheduler.py
index 6c0d0b068..82f33337f 100644
--- a/python/sglang/srt/managers/scheduler.py
+++ b/python/sglang/srt/managers/scheduler.py
@@ -54,7 +54,7 @@ from sglang.srt.disaggregation.encode_receiver import create_mm_receiver
 from sglang.srt.disaggregation.prefill import (
     PrefillBootstrapQueue,
     SchedulerDisaggregationPrefillMixin,
-    release_req_to_metadata_buffer,
+    maybe_release_metadata_buffer,
 )
 from sglang.srt.disaggregation.utils import (
     DisaggregationMode,
@@ -3586,9 +3586,17 @@ class Scheduler(
                 release_kv_cache(req, self.tree_cache)
             # For disaggregation prefill mode, free the metadata buffer index
             if self.disaggregation_mode == DisaggregationMode.PREFILL:
-                release_req_to_metadata_buffer(
+                bootstrap_pending = req.pending_bootstrap
+                maybe_release_metadata_buffer(
                     req, self.req_to_metadata_buffer_idx_allocator
                 )
+                if (
+                    bootstrap_pending
+                    and hasattr(req, "disagg_kv_sender")
+                    and req.disagg_kv_sender is not None
+                ):
+                    if hasattr(req.disagg_kv_sender, "abort"):
+                        req.disagg_kv_sender.abort()
 
             # For mamba radix cache
             if (
diff --git a/python/sglang/srt/managers/scheduler_components/metrics_reporter.py b/python/sglang/srt/managers/scheduler_components/metrics_reporter.py
index 786f765e4..50f739223 100644
--- a/python/sglang/srt/managers/scheduler_components/metrics_reporter.py
+++ b/python/sglang/srt/managers/scheduler_components/metrics_reporter.py
@@ -60,6 +60,8 @@ class PrefillStats:
     new_token_ratio: float
     num_running_reqs: QueueCount
     num_new_seqs: int  # len(can_run_list)
+    reprocessed_log_input_tokens: int = 0
+    reprocessed_log_hit_tokens: int = 0
     num_pending_tokens: int = 0
 
     @classmethod
@@ -73,6 +75,8 @@ class PrefillStats:
         return cls(
             log_input_tokens=adder.log_input_tokens,
             log_hit_tokens=adder.log_hit_tokens,
+            reprocessed_log_input_tokens=adder.reprocessed_log_input_tokens,
+            reprocessed_log_hit_tokens=adder.reprocessed_log_hit_tokens,
             new_token_ratio=adder.new_token_ratio,
             num_running_reqs=QueueCount.from_reqs(
                 running_reqs, enable_priority_scheduling
@@ -578,9 +582,16 @@ class SchedulerMetricsReporter:
                 )
 
             priority_enabled = self.scheduler.enable_priority_scheduling
-            total_tokens = prefill_stats.log_input_tokens + prefill_stats.log_hit_tokens
+            effective_input_tokens = (
+                prefill_stats.log_input_tokens
+                - prefill_stats.reprocessed_log_input_tokens
+            )
+            effective_hit_tokens = (
+                prefill_stats.log_hit_tokens - prefill_stats.reprocessed_log_hit_tokens
+            )
+            total_tokens = effective_input_tokens + effective_hit_tokens
             cache_hit_rate = (
-                prefill_stats.log_hit_tokens / total_tokens if total_tokens > 0 else 0.0
+                effective_hit_tokens / total_tokens if total_tokens > 0 else 0.0
             )
 
             # Basics
diff --git a/python/sglang/srt/observability/req_time_stats.py b/python/sglang/srt/observability/req_time_stats.py
index 326aace02..2de10730c 100644
--- a/python/sglang/srt/observability/req_time_stats.py
+++ b/python/sglang/srt/observability/req_time_stats.py
@@ -21,6 +21,8 @@ import uuid
 from dataclasses import dataclass, field
 from typing import TYPE_CHECKING, Any, Dict, List, Optional, Union
 
+from typing_extensions import Self
+
 from sglang.srt.disaggregation.utils import DisaggregationMode
 from sglang.srt.model_executor.forward_batch_info import ForwardMode
 from sglang.srt.observability.metrics_collector import (
@@ -230,7 +232,7 @@ class ReqTimeStatsBase:
     diff_realtime_monotonic: float = 0.0
 
     @classmethod
-    def new_from_obj(cls, obj: ReqTimeStatsBase, *args, **kwargs) -> "ReqTimeStatsBase":
+    def new_from_obj(cls, obj: Optional[ReqTimeStatsBase], *args, **kwargs) -> Self:
         calibrate_time_diff()
         new_obj = cls(*args, **kwargs)
         if obj is None:
@@ -668,6 +670,17 @@ class SchedulerReqTimeStats(ReqTimeStatsBase):
         if self.trace_ctx.tracing_enable:
             self.trace_ctx.trace_event("retract", 1, convert_time_to_realtime_ns(ts))
 
+    def reset_prefill_retry_time(self):
+        self.wait_queue_entry_time = 0.0
+        self.forward_entry_time = 0.0
+        self.prefill_finished_time = 0.0
+        self.completion_time = 0.0
+        self.prefill_transfer_queue_entry_time = 0.0
+        self.prefill_kv_transfer_finish_time = 0.0
+        self.last_forward_entry_time = 0.0
+        self.last_prefill_finished_time = 0.0
+        self.last_chunked_prefill_finish_time = 0.0
+
     def set_wait_queue_entry_time(self, ts=None):
         ts = ts or time.perf_counter()
         if self.wait_queue_entry_time == 0.0:
@@ -1008,22 +1021,22 @@ class SchedulerReqTimeStats(ReqTimeStatsBase):
                         and forward_duration >= 0
                     ), f"bootstrap_queue_duration={bootstrap_queue_duration} < 0 or queue_duration={queue_duration} < 0 or forward_duration={forward_duration} < 0"
 
-            # Break down bootstrap_queue_duration into sub-phases
-            if self.bootstrap_done_time > 0:
+            if (
+                self.bootstrap_done_time > 0
+                and self.prefill_bootstrap_queue_entry_time > 0
+            ):
                 bootstrap_duration = self.duration_between(
                     self.prefill_bootstrap_queue_entry_time, self.bootstrap_done_time
                 )
-                alloc_wait_duration = self.duration_between(
-                    self.bootstrap_done_time, self.wait_queue_entry_time
-                )
                 if SGLANG_TEST_REQUEST_TIME_STATS:
                     assert (
-                        bootstrap_duration >= 0 and alloc_wait_duration >= 0
-                    ), f"bootstrap_duration={bootstrap_duration} < 0 or alloc_wait_duration={alloc_wait_duration} < 0"
+                        bootstrap_duration >= 0
+                    ), f"bootstrap_duration={bootstrap_duration} < 0"
                 bootstrap_fields = (
                     f"bootstrap_duration={self.format_duration(bootstrap_duration)}, "
-                    f"alloc_wait_duration={self.format_duration(alloc_wait_duration)}, "
                 )
+            elif self.bootstrap_done_time > 0:
+                bootstrap_fields = f"bootstrap_done_time={self.format_wallclock(self.bootstrap_done_time)}, "
             else:
                 bootstrap_fields = f"bootstrap_queue_duration={self.format_duration(bootstrap_queue_duration)}, "
 
diff --git a/python/sglang/srt/server_args.py b/python/sglang/srt/server_args.py
index 0b436e812..6cf1314e5 100644
--- a/python/sglang/srt/server_args.py
+++ b/python/sglang/srt/server_args.py
@@ -36,7 +36,9 @@ from sglang.srt.arg_groups.argparse_actions import (
     DeprecatedStoreTrueAction,
     LoRAPathAction,
 )
-from sglang.srt.configs.linear_attn_model_registry import get_linear_attn_spec_by_arch
+from sglang.srt.configs.linear_attn_model_registry import (
+    get_linear_attn_spec_by_arch,
+)
 from sglang.srt.connector import ConnectorType
 from sglang.srt.distributed.device_communicators.mooncake_transfer_engine import (
     parse_ib_device_config,
@@ -818,6 +820,7 @@ class ServerArgs:
     num_reserved_decode_tokens: int = 512  # used for decode kv cache offload in PD
     # FIXME: hack to reduce ITL when decode bs is small
     disaggregation_decode_polling_interval: int = 1
+    optimistic_prefill_retries: int = 0
 
     # Encode prefill disaggregation
     encoder_only: bool = False
@@ -1776,6 +1779,7 @@ class ServerArgs:
             is_deepseek_dsa,
         )
 
+        self.uses_mamba_radix_cache = False
         if parse_connector_type(self.model_path) == ConnectorType.INSTANCE:
             return
 
@@ -1783,7 +1787,7 @@ class ServerArgs:
         model_arch = hf_config.architectures[0]
 
         _hybrid_spec = get_linear_attn_spec_by_arch(model_arch)
-        if _hybrid_spec is not None:
+        if _hybrid_spec is not None and _hybrid_spec.uses_mamba_radix_cache:
             self._handle_mamba_radix_cache(
                 model_arch=model_arch,
                 support_mamba_cache=_hybrid_spec.support_mamba_cache,
@@ -2620,6 +2624,8 @@ class ServerArgs:
         sm100_default_attention_backend: str = None,
         fallback_attention_backend: str = "triton",
     ):
+        self.uses_mamba_radix_cache = True
+
         if (
             is_sm100_supported()
             and self.attention_backend is None
@@ -4308,6 +4314,24 @@ class ServerArgs:
             )
 
     def _handle_other_validations(self):
+        # Handle optimistic prefill validation
+        if (
+            self.optimistic_prefill_retries > 0
+            and self.disaggregation_mode == "prefill"
+        ):
+            if self.pp_size > 1:
+                logger.warning("Optimistic prefill does not support pp_size > 1")
+                self.optimistic_prefill_retries = 0
+            elif self.enable_hierarchical_cache:
+                logger.warning("Optimistic prefill does not support hierarchical cache")
+                self.optimistic_prefill_retries = 0
+            elif getattr(self, "uses_mamba_radix_cache", False):
+                logger.warning(
+                    "Optimistic prefill does not support models that use "
+                    "mamba radix cache."
+                )
+                self.optimistic_prefill_retries = 0
+
         # Handle model inference tensor dump.
         if self.debug_tensor_dump_output_folder is not None:
             logger.warning(
@@ -6892,6 +6916,13 @@ class ServerArgs:
             help="The interval to poll requests in decode server. Can be set to >1 to reduce the overhead of this.",
         )
 
+        parser.add_argument(
+            "--optimistic-prefill-retries",
+            type=int,
+            default=ServerArgs.optimistic_prefill_retries,
+            help="Number of optimistic prefill retries that will skip the bootstrap wait. ",
+        )
+
         # Encode prefill disaggregation
         parser.add_argument(
             "--encoder-only",
diff --git a/test/registered/disaggregation/test_disaggregation_optimistic_prefill.py b/test/registered/disaggregation/test_disaggregation_optimistic_prefill.py
new file mode 100644
index 000000000..c99b5aa6f
--- /dev/null
+++ b/test/registered/disaggregation/test_disaggregation_optimistic_prefill.py
@@ -0,0 +1,202 @@
+import time
+import unittest
+import uuid
+from concurrent.futures import ThreadPoolExecutor, as_completed
+from types import SimpleNamespace
+
+import requests
+from prometheus_client.parser import text_string_to_metric_families
+
+from sglang.srt.disaggregation.prefill import should_force_retry
+from sglang.srt.environ import envs
+from sglang.test.ci.ci_register import register_cuda_ci
+from sglang.test.run_eval import run_eval
+from sglang.test.server_fixtures.disaggregation_fixture import (
+    PDDisaggregationServerBase,
+)
+from sglang.test.test_utils import DEFAULT_MODEL_NAME_FOR_TEST
+
+register_cuda_ci(est_time=120, stage="base-b", runner_config="2-gpu-large")
+
+
+FORCE_RETRY_PROB = 0.1
+
+
+def rid_that_forces_retry(prefix: str) -> str:
+    """Return a rid that the test retry sampler will select."""
+    for _ in range(1000):
+        rid = f"{prefix}{uuid.uuid4().hex}"
+        req = SimpleNamespace(
+            rid=rid,
+            is_retracted=False,
+            time_stats=SimpleNamespace(prefill_retry_count=0),
+        )
+        if should_force_retry(req):
+            return rid
+    raise RuntimeError("Failed to sample an optimistic prefill retry rid")
+
+
+class OptimisticPrefillRetryCounterMixin:
+    def _get_retry_counter(self) -> float:
+        response = requests.get(f"{self.prefill_url}/metrics")
+        response.raise_for_status()
+        total = 0.0
+        for family in text_string_to_metric_families(response.text):
+            if family.name != "sglang:num_prefill_retries":
+                continue
+            for sample in family.samples:
+                if sample.name == "sglang:num_prefill_retries_total":
+                    total += sample.value
+        return total
+
+    def assert_retry_counter_increases(self, fn):
+        before_retries = self._get_retry_counter()
+        result = fn()
+        after_retries = self._get_retry_counter()
+        self.assertGreater(after_retries, before_retries)
+        return result
+
+
+class TestOptimisticPrefill(
+    OptimisticPrefillRetryCounterMixin, PDDisaggregationServerBase
+):
+    @classmethod
+    def setUpClass(cls):
+        super().setUpClass()
+        cls._force_retry_prob_was_set = (
+            envs.SGLANG_TEST_FORCE_OPTIMISTIC_PREFILL_RETRY_PROB.is_set()
+        )
+        cls._force_retry_prob_value = (
+            envs.SGLANG_TEST_FORCE_OPTIMISTIC_PREFILL_RETRY_PROB.get()
+        )
+        envs.SGLANG_TEST_FORCE_OPTIMISTIC_PREFILL_RETRY_PROB.set(FORCE_RETRY_PROB)
+        cls.model = DEFAULT_MODEL_NAME_FOR_TEST
+        cls.extra_prefill_args = [
+            "--optimistic-prefill-retries",
+            "3",
+            "--chunked-prefill-size",
+            "128",
+            "--enable-metrics",
+            "--enable-request-time-stats-logging",
+        ]
+        cls.launch_all()
+
+    @classmethod
+    def tearDownClass(cls):
+        try:
+            super().tearDownClass()
+        finally:
+            if getattr(cls, "_force_retry_prob_was_set", False):
+                envs.SGLANG_TEST_FORCE_OPTIMISTIC_PREFILL_RETRY_PROB.set(
+                    cls._force_retry_prob_value
+                )
+            else:
+                envs.SGLANG_TEST_FORCE_OPTIMISTIC_PREFILL_RETRY_PROB.clear()
+
+    def test_gsm8k(self):
+        args = SimpleNamespace(
+            base_url=f"http://{self.base_host}:{self.lb_port}",
+            eval_name="gsm8k",
+            api="completion",
+            max_tokens=512,
+            num_examples=200,
+            num_threads=128,
+        )
+        metrics = self.assert_retry_counter_increases(lambda: run_eval(args))
+        print(f"Evaluation metrics: {metrics}")
+        self.assertGreater(metrics["score"], 0.62)
+        time.sleep(1)  # trigger memory check
+
+    def test_logprob(self):
+        request_id = rid_that_forces_retry("logprob-retry-")
+        prompt = f"{request_id}: " + "The capital of France is Paris. " * 900
+        j = self.assert_retry_counter_increases(
+            lambda: requests.post(
+                self.lb_url + "/generate",
+                json={
+                    "rid": request_id,
+                    "text": prompt,
+                    "sampling_params": {"temperature": 0, "max_new_tokens": 8},
+                    "return_logprob": True,
+                    "return_input_logprob": True,
+                    "logprob_start_len": 0,
+                },
+            ).json()
+        )
+        completion_tokens = j["meta_info"]["completion_tokens"]
+        input_logprobs = j["meta_info"]["input_token_logprobs"]
+        output_logprobs = j["meta_info"]["output_token_logprobs"]
+
+        self.assertGreater(j["meta_info"]["prompt_tokens"], 512)
+        assert len(output_logprobs) == completion_tokens
+        assert len(input_logprobs) > 0
+
+
+class TestOptimisticPrefillFailure(PDDisaggregationServerBase):
+    @classmethod
+    def setUpClass(cls):
+        super().setUpClass()
+        # enable optimistic prefill retry sampling and disagg failure prob
+        cls._force_retry_ctx = (
+            envs.SGLANG_TEST_FORCE_OPTIMISTIC_PREFILL_RETRY_PROB.override(
+                FORCE_RETRY_PROB
+            )
+        )
+        cls._force_retry_ctx.__enter__()
+        cls._disagg_failure_ctx = envs.SGLANG_TEST_DISAGG_FAILURE_PROB.override(
+            FORCE_RETRY_PROB
+        )
+        cls._disagg_failure_ctx.__enter__()
+
+        cls.model = DEFAULT_MODEL_NAME_FOR_TEST
+        cls.extra_prefill_args = [
+            "--optimistic-prefill-retries",
+            "3",
+            "--chunked-prefill-size",
+            "128",
+            "--enable-metrics",
+            "--enable-request-time-stats-logging",
+            "--load-format",
+            "dummy",
+        ]
+        cls.launch_all()
+
+    @classmethod
+    def tearDownClass(cls):
+        try:
+            super().tearDownClass()
+        finally:
+            if getattr(cls, "_force_retry_ctx", None):
+                cls._force_retry_ctx.__exit__(None, None, None)
+            if getattr(cls, "_disagg_failure_ctx", None):
+                cls._disagg_failure_ctx.__exit__(None, None, None)
+
+    def test_survive_requests(self):
+        # send many small requests to ensure the engine survives injected failures
+        n = 100
+        with ThreadPoolExecutor(max_workers=32) as executor:
+            futures = []
+            for i in range(n):
+                rid = f"survive-{i}-{uuid.uuid4().hex}"
+                futures.append(
+                    executor.submit(
+                        requests.post,
+                        self.lb_url + "/generate",
+                        json={
+                            "rid": rid,
+                            "text": "Hello world",
+                            "sampling_params": {"temperature": 0, "max_new_tokens": 4},
+                        },
+                        timeout=30,
+                    )
+                )
+            for future in as_completed(futures):
+                try:
+                    _ = future.result()
+                except Exception:
+                    pass
+        time.sleep(1)  # trigger memory check
+
+
+if __name__ == "__main__":
+    unittest.main()
diff --git a/test/registered/unit/managers/test_prefill_adder.py b/test/registered/unit/managers/test_prefill_adder.py
index 050f96f78..f532b630c 100644
--- a/test/registered/unit/managers/test_prefill_adder.py
+++ b/test/registered/unit/managers/test_prefill_adder.py
@@ -81,6 +81,7 @@ class TestPrefillAdder(CustomTestCase):
         req.output_ids = [0] * output_len
         req.sampling_params = SimpleNamespace(max_new_tokens=max_new_tokens)
         req.time_stats = SimpleNamespace(wait_queue_entry_time=wait_time)
+        req.retracted_stain = False
         req.finished.return_value = False
         return req