diff --git a/chain-test/src/test/scala/org/bitcoins/chain/blockchain/ChainHandlerTest.scala b/chain-test/src/test/scala/org/bitcoins/chain/blockchain/ChainHandlerTest.scala
index 543970b27e..2180da6fad 100644
--- a/chain-test/src/test/scala/org/bitcoins/chain/blockchain/ChainHandlerTest.scala
+++ b/chain-test/src/test/scala/org/bitcoins/chain/blockchain/ChainHandlerTest.scala
@@ -94,6 +94,16 @@ class ChainHandlerTest extends ChainDbUnitTest {
       } yield succeed
   }
 
+  it must "fail if we give a header that cannot be connected to anything" in {
+    chainHandler: ChainHandler =>
+      val newHeader = BlockHeaderHelper.badPrevHash
+      recoverToSucceededIf[RuntimeException] {
+        for {
+          result <- chainHandler.processHeader(newHeader)
+        } yield result
+      }
+  }
+
   // B
   // C -> D
   it must "handle a very basic reorg where one chain is one block behind the best chain" in {
diff --git a/chain/src/main/scala/org/bitcoins/chain/blockchain/ChainHandler.scala b/chain/src/main/scala/org/bitcoins/chain/blockchain/ChainHandler.scala
index 848f0e3e4c..349353dbe2 100644
--- a/chain/src/main/scala/org/bitcoins/chain/blockchain/ChainHandler.scala
+++ b/chain/src/main/scala/org/bitcoins/chain/blockchain/ChainHandler.scala
@@ -135,35 +135,44 @@ class ChainHandler(
         successfullyValidatedHeaders.distinct
       }
 
-      val chains = blockchainUpdates.map(_.blockchain)
+      if (headersToBeCreated.isEmpty) {
+        //this means we are given zero headers that were valid.
+        //Return a failure in this case to avoid issue 2365
+        //https://github.com/bitcoin-s/bitcoin-s/issues/2365
+        Future.failed(new RuntimeException(
+          s"Failed to connect any headers to our internal chain state, failures=$blockchainUpdates"))
+      } else {
+        val chains = blockchainUpdates.map(_.blockchain)
 
-      val createdF = blockHeaderDAO.createAll(headersToBeCreated)
+        val createdF = blockHeaderDAO.createAll(headersToBeCreated)
 
-      val newChainHandler = ChainHandler(blockHeaderDAO,
-                                         filterHeaderDAO,
-                                         filterDAO,
-                                         blockFilterCheckpoints =
-                                           blockFilterCheckpoints)
+        val newChainHandler = ChainHandler(blockHeaderDAO,
+                                           filterHeaderDAO,
+                                           filterDAO,
+                                           blockFilterCheckpoints =
+                                             blockFilterCheckpoints)
 
-      createdF.map { headers =>
-        if (chainConfig.chainCallbacks.onBlockHeaderConnected.nonEmpty) {
-          headersToBeCreated.reverseIterator.foldLeft(FutureUtil.unit) {
-            (acc, header) =>
-              for {
-                _ <- acc
-                _ <-
-                  chainConfig.chainCallbacks
-                    .executeOnBlockHeaderConnectedCallbacks(logger,
-                                                            header.height,
-                                                            header.blockHeader)
-              } yield ()
+        createdF.map { headers =>
+          if (chainConfig.chainCallbacks.onBlockHeaderConnected.nonEmpty) {
+            headersToBeCreated.reverseIterator.foldLeft(FutureUtil.unit) {
+              (acc, header) =>
+                for {
+                  _ <- acc
+                  _ <-
+                    chainConfig.chainCallbacks
+                      .executeOnBlockHeaderConnectedCallbacks(
+                        logger,
+                        header.height,
+                        header.blockHeader)
+                } yield ()
+            }
           }
+          chains.foreach { c =>
+            logger.info(
+              s"Processed headers from height=${c.height - headers.length} to ${c.height}. Best hash=${c.tip.hashBE.hex}")
+          }
+          newChainHandler
         }
-        chains.foreach { c =>
-          logger.info(
-            s"Processed headers from height=${c.height - headers.length} to ${c.height}. Best hash=${c.tip.hashBE.hex}")
-        }
-        newChainHandler
       }
     }
   }
diff --git a/core/src/main/scala/org/bitcoins/core/api/chain/ChainApi.scala b/core/src/main/scala/org/bitcoins/core/api/chain/ChainApi.scala
index 53d63e6344..8ba5b74254 100644
--- a/core/src/main/scala/org/bitcoins/core/api/chain/ChainApi.scala
+++ b/core/src/main/scala/org/bitcoins/core/api/chain/ChainApi.scala
@@ -19,7 +19,9 @@ import scala.concurrent.Future
 trait ChainApi extends ChainQueryApi {
 
   /**
-    * Adds a block header to our chain project
+    * Adds a block header to our chain project.
+    * This will return a failed future when the
+    * given header is invalid.
     * @param header
     * @return
     */
@@ -29,7 +31,9 @@ trait ChainApi extends ChainQueryApi {
 
   /** Process all of the given headers and returns a new [[ChainApi chain api]]
     * that contains these headers. This method processes headers in the order
-    * that they are given. If the headers are out of order, this method will fail
+    * that they are given. If the headers are out of order, this method will fail.
+    *
+    * This method will also fail when there are zero headers given that are valid.
     * @param headers
     * @return
     */
diff --git a/node-test/src/test/scala/org/bitcoins/node/networking/peer/DataMessageHandlerTest.scala b/node-test/src/test/scala/org/bitcoins/node/networking/peer/DataMessageHandlerTest.scala
index 1dbe943e7c..4dc1e99a79 100644
--- a/node-test/src/test/scala/org/bitcoins/node/networking/peer/DataMessageHandlerTest.scala
+++ b/node-test/src/test/scala/org/bitcoins/node/networking/peer/DataMessageHandlerTest.scala
@@ -105,7 +105,9 @@ class DataMessageHandlerTest extends NodeUnitTest {
 
       val callback: OnBlockHeadersReceived = (headers: Vector[BlockHeader]) => {
         Future {
-          resultP.success(headers)
+          if (!resultP.isCompleted) {
+            resultP.success(headers)
+          }
           ()
         }
       }