diff --git a/lbry/wallet/header.py b/lbry/wallet/header.py
index 1375d5442..6af943e3b 100644
--- a/lbry/wallet/header.py
+++ b/lbry/wallet/header.py
@@ -47,6 +47,8 @@ class Headers:
         self._size: Optional[int] = None
         self.chunk_getter: Optional[Callable] = None
         self.executor = ThreadPoolExecutor(1)
+        self.known_missing_checkpointed_chunks = set()
+        self.check_chunk_lock = asyncio.Lock()
 
     async def open(self):
         if not self.executor:
@@ -57,6 +59,8 @@ class Headers:
             else:
                 self.io = open(self.path, 'r+b')
         self._size = self.io.seek(0, os.SEEK_END) // self.header_size
+        await self.ensure_checkpointed_size()
+        await self.get_all_missing_headers()
 
     async def close(self):
         if self.executor:
@@ -140,14 +144,19 @@ class Headers:
         self.io.seek(start * self.header_size, os.SEEK_SET)
         return self.hash_header(self.io.read(count * self.header_size)).decode()
 
-    async def ensure_tip(self):
-        if self.checkpoints:
-            await self.ensure_chunk_at(max(self.checkpoints.keys()))
+    async def ensure_checkpointed_size(self):
+        max_checkpointed_height = max(self.checkpoints.keys() or [-1])
+        if self.height < max_checkpointed_height:
+            self._write(max_checkpointed_height, bytes([0] * self.header_size * 1000))
 
     async def ensure_chunk_at(self, height):
-        if await self.has_header(height):
-            log.debug("has header %s", height)
-            return
+        async with self.check_chunk_lock:
+            if await self.has_header(height):
+                log.debug("has header %s", height)
+                return
+            return await self.fetch_chunk(height)
+
+    async def fetch_chunk(self, height):
         log.info("on-demand fetching height %s", height)
         start = (height // 1000) * 1000
         headers = await self.chunk_getter(start)  # pylint: disable=not-callable
@@ -156,7 +165,10 @@ class Headers:
         )
         chunk_hash = self.hash_header(chunk).decode()
         if self.checkpoints.get(start) == chunk_hash:
-            return await asyncio.get_running_loop().run_in_executor(self.executor, self._write, start, chunk)
+            await asyncio.get_running_loop().run_in_executor(self.executor, self._write, start, chunk)
+            if start in self.known_missing_checkpointed_chunks:
+                self.known_missing_checkpointed_chunks.remove(start)
+            return
         elif start not in self.checkpoints:
             return  # todo: fixme
         raise Exception(
@@ -164,12 +176,27 @@ class Headers:
         )
 
     async def has_header(self, height):
+        normalized_height = (height // 1000) * 1000
+        if normalized_height in self.checkpoints:
+            return normalized_height not in self.known_missing_checkpointed_chunks
+
         def _has_header(height):
             empty = '56944c5d3f98413ef45cf54545538103cc9f298e0575820ad3591376e2e0f65d'
             all_zeroes = '789d737d4f448e554b318c94063bbfa63e9ccda6e208f5648ca76ee68896557b'
             return self.chunk_hash(height, 1) not in (empty, all_zeroes)
         return await asyncio.get_running_loop().run_in_executor(self.executor, _has_header, height)
 
+    async def get_all_missing_headers(self):
+        # Heavy operation done in one optimized shot
+        def _io_checkall():
+            for chunk_height, expected_hash in reversed(list(self.checkpoints.items())):
+                if chunk_height in self.known_missing_checkpointed_chunks:
+                    continue
+                if self.chunk_hash(chunk_height, 1000) != expected_hash:
+                    self.known_missing_checkpointed_chunks.add(chunk_height)
+            return self.known_missing_checkpointed_chunks
+        return await asyncio.get_running_loop().run_in_executor(self.executor, _io_checkall)
+
     @property
     def height(self) -> int:
         return len(self)-1
diff --git a/lbry/wallet/ledger.py b/lbry/wallet/ledger.py
index 0e648789b..907aec8ba 100644
--- a/lbry/wallet/ledger.py
+++ b/lbry/wallet/ledger.py
@@ -344,15 +344,13 @@ class Ledger(metaclass=LedgerRegistry):
         return max(self.headers.height, self._download_height)
 
     async def initial_headers_sync(self):
-        target = self.network.remote_height + 1
         get_chunk = partial(self.network.retriable_call, self.network.get_headers, count=1000, b64=True)
         self.headers.chunk_getter = get_chunk
 
         async def doit():
-            for height in reversed(range(0, target)):
-                async with self._header_processing_lock:
+            async with self._header_processing_lock:
+                for height in reversed(sorted(self.headers.known_missing_checkpointed_chunks)):
                     await self.headers.ensure_chunk_at(height)
-        await self.headers.ensure_tip()
         self._update_tasks.add(doit())
         await self.update_headers()
 
diff --git a/tests/unit/wallet/test_headers.py b/tests/unit/wallet/test_headers.py
index 1d1589648..52dfc2117 100644
--- a/tests/unit/wallet/test_headers.py
+++ b/tests/unit/wallet/test_headers.py
@@ -1,12 +1,15 @@
 import os
 import asyncio
 import tempfile
-from binascii import hexlify, unhexlify
+from binascii import unhexlify
 
-from lbry.crypto.hash import sha256
 from lbry.wallet.util import ArithUint256
 from lbry.testcase import AsyncioTestCase
-from lbry.wallet.ledger import Headers
+from lbry.wallet.ledger import Headers as _Headers
+
+
+class Headers(_Headers):
+    checkpoints = {}
 
 
 def block_bytes(blocks):