diff --git a/src/main.cpp b/src/main.cpp
index a4b8ffe81..79dd69ec8 100644
--- a/src/main.cpp
+++ b/src/main.cpp
@@ -332,6 +332,8 @@ struct CNodeState {
     CBlockIndex *pindexLastCommonBlock;
     //! Whether we've started headers synchronization with this peer.
     bool fSyncStarted;
+    //! When to potentially disconnect peer for stalling headers download
+    int64_t nHeadersSyncTimeout;
     //! Since when we're stalling block download progress (in microseconds), or 0.
     int64_t nStallingSince;
     list<QueuedBlock> vBlocksInFlight;
@@ -348,6 +350,7 @@ struct CNodeState {
         hashLastUnknownBlock.SetNull();
         pindexLastCommonBlock = NULL;
         fSyncStarted = false;
+        nHeadersSyncTimeout = 0;
         nStallingSince = 0;
         nBlocksInFlight = 0;
         nBlocksInFlightValidHeaders = 0;
@@ -514,7 +517,7 @@ void FindNextBlocksToDownload(NodeId nodeid, unsigned int count, std::vector<CBl
     // Make sure pindexBestKnownBlock is up to date, we'll need it.
     ProcessBlockAvailability(nodeid);
 
-    if (state->pindexBestKnownBlock == NULL || state->pindexBestKnownBlock->nChainWork < chainActive.Tip()->nChainWork) {
+    if (state->pindexBestKnownBlock == NULL || state->pindexBestKnownBlock->nChainWork < chainActive.Tip()->nChainWork || state->pindexBestKnownBlock->nChainWork < UintToArith256(Params().GetConsensus().nMinimumChainWork)) {
         // This peer has nothing interesting.
         return;
     }
@@ -7648,6 +7651,7 @@ bool SendMessages(const Consensus::Params& params, CNode* pto)
             // Only actively request headers from a single peer, unless we're close to today.
             if ((nSyncStarted == 0 && fFetch) || pindexBestHeader->GetBlockTime() > GetTime() - 24 * 60 * 60) {
                 state.fSyncStarted = true;
+                state.nHeadersSyncTimeout = GetTimeMicros() + HEADERS_DOWNLOAD_TIMEOUT_BASE + HEADERS_DOWNLOAD_TIMEOUT_PER_HEADER * (EstimateNetHeight(params, pindexBestHeader->nHeight, pindexBestHeader->GetBlockTime()) - pindexBestHeader->nHeight);
                 nSyncStarted++;
                 const CBlockIndex *pindexStart = pindexBestHeader;
                 /* If possible, start at the block preceding the currently
@@ -7833,6 +7837,38 @@ bool SendMessages(const Consensus::Params& params, CNode* pto)
                 pto->fDisconnect = true;
             }
         }
+        // Check for headers sync timeouts
+        if (state.fSyncStarted && state.nHeadersSyncTimeout < std::numeric_limits<int64_t>::max()) {
+            // Detect whether this is a stalling initial-headers-sync peer
+            if (pindexBestHeader->GetBlockTime() <= GetTime() - 24*60*60) {
+                if (nNow > state.nHeadersSyncTimeout && nSyncStarted == 1 && (nPreferredDownload - state.fPreferredDownload >= 1)) {
+                    // Disconnect a (non-whitelisted) peer if it is our only sync peer,
+                    // and we have others we could be using instead.
+                    // Note: If all our peers are inbound, then we won't
+                    // disconnect our sync peer for stalling; we have bigger
+                    // problems if we can't get any outbound peers.
+                    if (!pto->fWhitelisted) {
+                        LogPrintf("Timeout downloading headers from peer=%d, disconnecting\n", pto->GetId());
+                        pto->fDisconnect = true;
+                        return true;
+                    } else {
+                        LogPrintf("Timeout downloading headers from whitelisted peer=%d, not disconnecting\n", pto->GetId());
+                        // Reset the headers sync state so that we have a
+                        // chance to try downloading from a different peer.
+                        // Note: this will also result in at least one more
+                        // getheaders message to be sent to
+                        // this peer (eventually).
+                        state.fSyncStarted = false;
+                        nSyncStarted--;
+                        state.nHeadersSyncTimeout = 0;
+                    }
+                }
+            } else {
+                // After we've caught up once, reset the timeout so we can't trigger
+                // disconnect later.
+                state.nHeadersSyncTimeout = std::numeric_limits<int64_t>::max();
+            }
+        }
 
         //
         // Message: getdata (blocks)
diff --git a/src/main.h b/src/main.h
index 0034a4969..5b57baad5 100644
--- a/src/main.h
+++ b/src/main.h
@@ -98,6 +98,10 @@ static const int DEFAULT_SCRIPTCHECK_THREADS = 0;
 static const int MAX_BLOCKS_IN_TRANSIT_PER_PEER = 16;
 /** Timeout in seconds during which a peer must stall block download progress before being disconnected. */
 static const unsigned int BLOCK_STALLING_TIMEOUT = 2;
+/** Headers download timeout expressed in microseconds
+ *  Timeout = base + per_header * (expected number of headers) */
+static constexpr int64_t HEADERS_DOWNLOAD_TIMEOUT_BASE = 30 * 60 * 1000000; // 30 minutes
+static constexpr int64_t HEADERS_DOWNLOAD_TIMEOUT_PER_HEADER = 10000; // 10 ms/header
 /** Number of headers sent in one getheaders result. We rely on the assumption that if a peer sends
  *  less than this number, we reached its tip. Changing this value is a protocol upgrade. */
 static const unsigned int MAX_HEADERS_RESULTS = 160;