diff --git a/Code/GraphMol/ChemTransforms/MolFragmenter.cpp b/Code/GraphMol/ChemTransforms/MolFragmenter.cpp
index 340540373..54cf51450 100644
--- a/Code/GraphMol/ChemTransforms/MolFragmenter.cpp
+++ b/Code/GraphMol/ChemTransforms/MolFragmenter.cpp
@@ -11,6 +11,7 @@
 #include "MolFragmenter.h"
 
 #include <GraphMol/Depictor/RDDepictor.h>
+#include <GraphMol/QueryBond.h>
 #include <GraphMol/RDKitBase.h>
 #include <GraphMol/SmilesParse/SmilesParse.h>
 #include <GraphMol/SmilesParse/SmilesWrite.h>
@@ -464,6 +465,12 @@ ROMol *fragmentOnBonds(
     Bond::BondDir bD = bond->getBondDir();
     unsigned int bondidx;
     auto nbr_bond_stereo = getNbrBondStereo(*res, bond);
+    // Grab a copy of any query on the outgoing bond if it will be needed later.
+    auto outBond = res->getBondBetweenAtoms(bidx, eidx);
+    std::unique_ptr<Bond::QUERYBOND_QUERY> outQuery;
+    if (!bondTypes && outBond->hasQuery()) {
+      outQuery.reset(outBond->getQuery()->copy());
+    }
     res->removeBond(bidx, eidx);
     if (nCutsPerAtom) {
       (*nCutsPerAtom)[bidx] += 1;
@@ -491,12 +498,23 @@ ROMol *fragmentOnBonds(
       if (bD == Bond::ENDDOWNRIGHT || bD == Bond::ENDUPRIGHT) {
         res->getBondWithIdx(bondidx)->setBondDir(bD);
       }
+      // transfer any query from the outgoing bond to the new one
+      if (outQuery) {
+        auto qb = std::make_unique<QueryBond>(*res->getBondWithIdx(bondidx));
+        qb->setQuery(outQuery->copy());
+        res->replaceBond(bondidx, qb.get());
+      }
 
       unsigned int idx2 = res->addAtom(at2, false, true);
       bondidx = res->addBond(bidx, at2->getIdx(), bT) - 1;
       // this bond starts at the same atom, so its direction should always be
       // correct:
       res->getBondWithIdx(bondidx)->setBondDir(bD);
+      if (outQuery) {
+        auto qb = std::make_unique<QueryBond>(*res->getBondWithIdx(bondidx));
+        qb->setQuery(outQuery->copy());
+        res->replaceBond(bondidx, qb.get());
+      }
 
       // restore stereo atoms
       for (auto &stereo_atoms : nbr_bond_stereo) {
diff --git a/Code/GraphMol/ChemTransforms/MolFragmenter.h b/Code/GraphMol/ChemTransforms/MolFragmenter.h
index cd7c876dc..cdc1ba800 100644
--- a/Code/GraphMol/ChemTransforms/MolFragmenter.h
+++ b/Code/GraphMol/ChemTransforms/MolFragmenter.h
@@ -46,6 +46,9 @@ struct RDKIT_CHEMTRANSFORMS_EXPORT FragmenterBondType {
 
   \return a new ROMol with the modifications
   The client is responsible for deleting this molecule.
+  Unless bondTypes is provided, the bonds to the new dummy atoms will be
+  of the same type as the bond that is broken, and any queries on the
+  broken bonds transferred to the new bonds.
 
 */
 RDKIT_CHEMTRANSFORMS_EXPORT ROMol *fragmentOnBonds(
diff --git a/Code/GraphMol/ChemTransforms/catch_tests.cpp b/Code/GraphMol/ChemTransforms/catch_tests.cpp
index a059a4a3d..cfe3b7841 100644
--- a/Code/GraphMol/ChemTransforms/catch_tests.cpp
+++ b/Code/GraphMol/ChemTransforms/catch_tests.cpp
@@ -584,4 +584,70 @@ TEST_CASE(
 
     CHECK(MolToSmiles(*res) == "[1*]/C=C/N.[2*]CC");
   }
+}
+
+TEST_CASE(
+    "Github #9009: fragmentOnBonds should transfer queries on deleted bonds") {
+  // Basic test
+  auto m1 = "c1ccccc1-C1CCCCC1"_smarts;
+  REQUIRE(m1);
+  auto bond1 = m1->getBondWithIdx(1);
+  REQUIRE(bond1);
+  REQUIRE(bond1->hasQuery());
+  auto splitM1(
+      MolFragmenter::fragmentOnBonds(*m1, std::vector<unsigned int>{1, 5}));
+  REQUIRE(splitM1);
+  auto nb1 = splitM1->getBondWithIdx(11);
+  REQUIRE(nb1);
+  CHECK(nb1->hasQuery());
+  CHECK(nb1->getQuery()->getDescription() == "SingleOrAromaticBond");
+
+  auto nb2 = splitM1->getBondWithIdx(12);
+  REQUIRE(nb2);
+  CHECK(nb2->hasQuery());
+  CHECK(nb2->getQuery()->getDescription() == "SingleOrAromaticBond");
+
+  auto nb3 = splitM1->getBondWithIdx(13);
+  REQUIRE(nb3);
+  CHECK(nb3->hasQuery());
+  CHECK(nb3->getQuery()->getDescription() == "BondOrder");
+  auto nb4 = splitM1->getBondWithIdx(14);
+  REQUIRE(nb4);
+  CHECK(nb4->hasQuery());
+  CHECK(nb4->getQuery()->getDescription() == "BondOrder");
+
+  // Check it does nothing if there isn't a query
+  auto m2 = "c1ccccc1"_smiles;
+  REQUIRE(m2);
+  auto bond2 = m2->getBondWithIdx(1);
+  REQUIRE(bond2);
+  REQUIRE(!bond2->hasQuery());
+  auto splitM2(
+      MolFragmenter::fragmentOnBonds(*m2, std::vector<unsigned int>{1}));
+  REQUIRE(splitM2);
+  auto nb5 = splitM2->getBondWithIdx(5);
+  REQUIRE(nb5);
+  CHECK(!nb5->hasQuery());
+  auto nb6 = splitM2->getBondWithIdx(6);
+  REQUIRE(nb6);
+  CHECK(!nb6->hasQuery());
+
+  // Check it does nothing if bond types are specified
+  auto m3 = "c1ccccc1"_smiles;
+  REQUIRE(m3);
+  auto bond3 = m3->getBondWithIdx(1);
+  REQUIRE(bond3);
+  REQUIRE(!bond3->hasQuery());
+  auto dummyLabels =
+      std::vector<std::pair<unsigned int, unsigned int>>{{25, 26}};
+  auto newTypes = std::vector<Bond::BondType>{Bond::DOUBLE};
+  auto splitM3(MolFragmenter::fragmentOnBonds(*m3, std::vector<unsigned int>{1},
+                                              true, &dummyLabels, &newTypes));
+  REQUIRE(splitM3);
+  auto nb7 = splitM3->getBondWithIdx(5);
+  REQUIRE(nb7);
+  CHECK(!nb7->hasQuery());
+  auto nb8 = splitM3->getBondWithIdx(6);
+  REQUIRE(nb8);
+  CHECK(!nb8->hasQuery());
 }
\ No newline at end of file
diff --git a/Code/GraphMol/SynthonSpaceSearch/SynthonSpaceSearch_details.cpp b/Code/GraphMol/SynthonSpaceSearch/SynthonSpaceSearch_details.cpp
index 5dfe27451..d35ecc01d 100644
--- a/Code/GraphMol/SynthonSpaceSearch/SynthonSpaceSearch_details.cpp
+++ b/Code/GraphMol/SynthonSpaceSearch/SynthonSpaceSearch_details.cpp
@@ -366,8 +366,6 @@ void doPartInitialFragmentation(
   bool timedOut = false;
   while (true) {
     std::int64_t thisRB = ++mostRecentRingBond;
-    // std::cout << "ring bond " << thisRB << " of " << lastRingBond << " and "
-    // << tmpFrags.size() << std::endl;
     if (thisRB > lastRingBond) {
       break;
     }
@@ -575,7 +573,7 @@ std::vector<std::vector<std::unique_ptr<ROMol>>> splitMolecule(
     return fragments;
   }
 
-  // Keep unique SMILES onlyu
+  // Keep unique SMILES only
   std::sort(tmpFrags.begin(), tmpFrags.end(),
             [](const auto &lhs, const auto &rhs) -> bool {
               return lhs.first < rhs.first;
diff --git a/Code/GraphMol/SynthonSpaceSearch/SynthonSpaceSearcher.cpp b/Code/GraphMol/SynthonSpaceSearch/SynthonSpaceSearcher.cpp
index 81e1ffd59..ad7ac11c5 100644
--- a/Code/GraphMol/SynthonSpaceSearch/SynthonSpaceSearcher.cpp
+++ b/Code/GraphMol/SynthonSpaceSearch/SynthonSpaceSearcher.cpp
@@ -106,8 +106,8 @@ void SynthonSpaceSearcher::search(const SearchResultCallback &cb) {
   }
 
   // Do any remaining.
-  if ((d_params.maxHits == -1 || hitCount < d_params.maxHits) &&
-      !stop && !toTry.empty()) {
+  if ((d_params.maxHits == -1 || hitCount < d_params.maxHits) && !stop &&
+      !toTry.empty()) {
     std::vector<std::unique_ptr<ROMol>> partResults;
     processToTrySet(toTry, endTime, partResults);
     cb(partResults);
@@ -393,11 +393,8 @@ void sortAndUniquifyToTry(
   std::vector<std::pair<const SynthonSpaceHitSet *, std::vector<size_t>>>
       newToTry;
   newToTry.reserve(tmp.size());
-  std::transform(
-      tmp.begin(), tmp.end(),
-      back_inserter(newToTry), [&](const auto &p) -> auto{
-        return toTry[p.first];
-      });
+  std::transform(tmp.begin(), tmp.end(), back_inserter(newToTry),
+                 [&](const auto &p) -> auto { return toTry[p.first]; });
   toTry = newToTry;
 }
 
diff --git a/Code/GraphMol/SynthonSpaceSearch/substructure_search_catch_tests.cpp b/Code/GraphMol/SynthonSpaceSearch/substructure_search_catch_tests.cpp
index 7dcfcde7f..df289b219 100644
--- a/Code/GraphMol/SynthonSpaceSearch/substructure_search_catch_tests.cpp
+++ b/Code/GraphMol/SynthonSpaceSearch/substructure_search_catch_tests.cpp
@@ -152,12 +152,13 @@ TEST_CASE("S Amide 1") {
   CHECK(resSmi == enumSmi);
 
   resSmi.clear();
-  SearchResultCallback cb = [&resSmi](const std::vector<std::unique_ptr<ROMol>> &r) {
-    for (auto &elem : r) {
-      resSmi.insert(MolToSmiles(*elem));
-    }
-    return false;
-  };
+  SearchResultCallback cb =
+      [&resSmi](const std::vector<std::unique_ptr<ROMol>> &r) {
+        for (auto &elem : r) {
+          resSmi.insert(MolToSmiles(*elem));
+        }
+        return false;
+      };
   synthonspace.substructureSearch(*queryMol, cb, matchParams, params);
   CHECK(resSmi == enumSmi);
 }
@@ -181,13 +182,14 @@ TEST_CASE("Search Callback returns true") {
   params.toTryChunkSize = 2;
   std::set<std::string> cbSmi;
   bool retval = false;
-  SearchResultCallback cb = [&cbSmi,&retval](const std::vector<std::unique_ptr<ROMol>> &r) {
-    for (auto &elem : r) {
-      CHECK(r.size() == 2);
-      cbSmi.insert(MolToSmiles(*elem));
-    }
-    return retval;
-  };
+  SearchResultCallback cb =
+      [&cbSmi, &retval](const std::vector<std::unique_ptr<ROMol>> &r) {
+        for (auto &elem : r) {
+          CHECK(r.size() == 2);
+          cbSmi.insert(MolToSmiles(*elem));
+        }
+        return retval;
+      };
   synthonspace.substructureSearch(*queryMol, cb, matchParams, params);
   CHECK(cbSmi.size() == 6);
 
@@ -833,3 +835,37 @@ TEST_CASE("Enhanced Stereochemistry - Github 8650") {
   REQUIRE(synthons[0].size() == 1);
   CHECK(synthons[0][0].second->getSmiles() == "C[C@H]1CC[C@H](CC1)F |&1:1,4|");
 }
+
+TEST_CASE("Github 9009") {
+  {
+    // Single bond to "extra" aromatic C
+    SynthonSpace space;
+    std::istringstream iss(
+        R"(SMILES	synton_id	synton#	reaction_id	release
+O=c1ccncn1[1*]	192	1	r2	1
+[1*]c1ccccc1	227	2	r2	1
+)");
+    bool cancelled = false;
+    space.readStream(iss, cancelled);
+    auto q1 = "O=c1n([c])cncc1"_smarts;
+    auto res1 = space.substructureSearch(*q1);
+    CHECK(res1.getHitMolecules().size() == 1);
+    auto q2 = "O=c1n([a])cncc1"_smarts;
+    auto res2 = space.substructureSearch(*q2);
+    CHECK(res2.getHitMolecules().size() == 1);
+  }
+  {
+    // Check that aromatic bond works
+    SynthonSpace space;
+    std::istringstream iss(
+        R"(SMILES	synton_id	synton#	reaction_id	release
+[1*]C=CC=C[2*]	192	1	r2	1
+O=C1NC=NC([2*])=C1[1*]	227	2	r2	1
+)");
+    bool cancelled = false;
+    space.readStream(iss, cancelled);
+    auto q3 = "O=c1ncncc1c"_smarts;
+    auto res3 = space.substructureSearch(*q3);
+    CHECK(res3.getHitMolecules().size() == 1);
+  }
+}
\ No newline at end of file