diff --git a/Code/GraphMol/FindStereo.cpp b/Code/GraphMol/FindStereo.cpp
index 83304732f..72dbfda3c 100644
--- a/Code/GraphMol/FindStereo.cpp
+++ b/Code/GraphMol/FindStereo.cpp
@@ -826,40 +826,38 @@ bool updateAtoms(ROMol &mol, const std::vector<unsigned int> &aranks,
 
           // if this was creating possible ring stereo, update that info now
           if (possibleRingStereoAtoms[aidx]) {
-            --possibleRingStereoAtoms[aidx];
-            if (!possibleRingStereoAtoms[aidx]) {
-              needAnotherRound = true;
-              // we're no longer in any ring with possible ring stereo. Go
-              // update all the other atoms/bonds in rings that we're in:
-              for (unsigned int ridx = 0;
-                   ridx < mol.getRingInfo()->atomRings().size(); ++ridx) {
-                const auto &aring = mol.getRingInfo()->atomRings()[ridx];
-                unsigned int nHere = 0;
-                for (auto raidx : aring) {
-                  // Ring stereo changed, so un-fix atoms in this ring so we can
-                  // recheck them in the next iteration, for the case that they
-                  // are no longer after the current atom was declared
-                  // non-chiral
-                  fixedAtoms[raidx] = false;
-                  nHere += (possibleRingStereoAtoms[raidx] > 0);
-                }
-                if (nHere <= 1) {
-                  // if the ring can't transmit stereo anymore, update the
-                  // counts
-                  if (nHere == 1) {
-                    // update the last potential ring stereo atom in the ring,
-                    // since it can't have ring stereo alone.
-                    for (auto raidx : aring) {
-                      if (possibleRingStereoAtoms[raidx]) {
-                        --possibleRingStereoAtoms[raidx];
-                        break;
-                      }
+            possibleRingStereoAtoms[aidx] = 0;
+            needAnotherRound = true;
+            // we're no longer in any ring with possible ring stereo. Go
+            // update all the other atoms/bonds in rings that we're in:
+            for (unsigned int ridx = 0;
+                 ridx < mol.getRingInfo()->atomRings().size(); ++ridx) {
+              const auto &aring = mol.getRingInfo()->atomRings()[ridx];
+              unsigned int nHere = 0;
+              for (auto raidx : aring) {
+                // Ring stereo changed, so un-fix atoms in this ring so we can
+                // recheck them in the next iteration, for the case that they
+                // are no longer after the current atom was declared
+                // non-chiral
+                fixedAtoms[raidx] = false;
+                nHere += (possibleRingStereoAtoms[raidx] > 0);
+              }
+              if (nHere <= 1) {
+                // if the ring can't transmit stereo anymore, update the
+                // counts
+                if (nHere == 1) {
+                  // update the last potential ring stereo atom in the ring,
+                  // since it can't have ring stereo alone.
+                  for (auto raidx : aring) {
+                    if (possibleRingStereoAtoms[raidx]) {
+                      --possibleRingStereoAtoms[raidx];
+                      break;
                     }
                   }
-                  for (auto rbidx : mol.getRingInfo()->bondRings()[ridx]) {
-                    if (possibleRingStereoBonds[rbidx]) {
-                      --possibleRingStereoBonds[rbidx];
-                    }
+                }
+                for (auto rbidx : mol.getRingInfo()->bondRings()[ridx]) {
+                  if (possibleRingStereoBonds[rbidx]) {
+                    --possibleRingStereoBonds[rbidx];
                   }
                 }
               }
diff --git a/Code/GraphMol/catch_canon.cpp b/Code/GraphMol/catch_canon.cpp
index 84c692092..afbdd29cb 100644
--- a/Code/GraphMol/catch_canon.cpp
+++ b/Code/GraphMol/catch_canon.cpp
@@ -1172,8 +1172,7 @@ TEST_CASE("Canonicalization issues watch (see GitHub Issue #8775)") {
       {R"smi(C1=C\CCCCCC/C=C/C=C/1)smi", true, true},                   // #8759
       {R"smi(O=C=NC1=CC2C3=C(C=C1)C2=C(N=C=O)C=C3)smi", false, false},  // #8721
       {R"smi(O=C(c1ccccc1C(=O)N1C(=O)c2ccccc2C1=O)N1C(=O)c2ccccc2C1=O)smi",
-       false, false},                                                   // #8721
-      {R"smi(O=C=NC1=CC2C3=C(C=C1)C2=C(N=C=O)C=C3)smi", false, false},  // #8721
+       false, false},  // #8721
       {R"smi(O=[N+]([O-])c1cc/c2c(c1)=C(c1ccccc1)/N=c1\\ccc([N+](=O)[O-])cc1=C(c1ccccc1)/N=2)smi",
        false, true},  // #8721
       {R"smi(C=Cc1c(C)/c2[n-]c1=C=c1[n-]/c(c(CC)c1C)=C\\c1[n-]c3c(c1C)C(=O)[C@H](C(=O)OC)/C3=C1/[NH+]=C(/C=2)[C@@H](C)[C@@H]1CCC(=O)OC/C=C(\\C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C.[Mg+2])smi",
@@ -1220,11 +1219,6 @@ TEST_CASE("Canonicalization issues watch (see GitHub Issue #8775)") {
       {R"smi([H]/N=C(C=C)\C(/N=C\[O-])=N\[H])smi", false, true},  // #7759
       {R"smi([H]N=C(/N=C\[O-])/C(C=C)=N\[H])smi", true, true},    // #7759
       {R"smi([H]/N=C(/C=C)C(=N)/N=C\[O-])smi", true, true},       // #7759
-      {R"smi([H]/N=C(/C=C)C(=N)/N=C\[O-])smi", true, true},       // #7759
-      {R"smi([C@H]12[C@H]3[C@@H]4[C@H]5[C@@H]([C@H]1N24)N53)smi", false,
-       true},  // #7759
-      {R"smi([C@H]12[C@H]3[C@H]4[C@@H]5[C@@H]([C@H]1N25)N34)smi", false,
-       true},  // #7759
       {R"smi([C@H]12[C@H]3[C@@H]4[C@H]5[C@@H]([C@H]1N24)N53)smi", false,
        true},  // #7759
       {R"smi([C@H]12[C@H]3[C@H]4[C@@H]5[C@@H]([C@H]1N25)N34)smi", false,
@@ -1234,12 +1228,10 @@ TEST_CASE("Canonicalization issues watch (see GitHub Issue #8775)") {
       {R"smi([CH]1O[C@H]2CN(C2)[C@]12CC2)smi", false, true},       // #7759
       {R"smi([CH]1[C@H]2C[C@H](C2)[C@]12CCC2)smi", false, true},   // #7759
       {R"smi([CH]1[C@H]2C[C@H](C2)[C@@]12COC2)smi", false, true},  // #7759
-      {R"smi(O=C1[C]2C[C@H](C2)[C@@]12CC2)smi", false, false},     // #7759
+      {R"smi(O=C1[C]2C[C@H](C2)[C@@]12CC2)smi", false, true},      // #7759
       {R"smi(O=C1[C@H]2C[C](C2)[C@@]12CC2)smi", false, true},      // #7759
       {R"smi(C1[C@H]2[C@@H]3C[C@H]4[C@@H]3[C@@H]1[C@@H]24)smi", false,
        true},  // #7759
-      {R"smi([C@H]12[C@H]3[C@@H]4[C@H]5[C@@H]([C@H]1N24)N53)smi", false,
-       true},  // #7759
       {R"smi(C[C@]12[C@@H]3[C@@H]1C[C@H]1[C@H]2[C@]31C)smi", false,
        true},                                                      // #7759
       {R"smi([O][C@]12C[C@H](C1)[C@@]1(CC1)C2)smi", false, true},  // #7759
@@ -1301,7 +1293,7 @@ TEST_CASE("Canonicalization issues watch (see GitHub Issue #8775)") {
       {R"smi([CH-]1O[C@H]2C[C@H](C2)[C@]12CC2)smi", false, true},       // #7759
       {R"smi([CH-]1[C@H]2C[C@H](C2)[C@]12CCC2)smi", false, true},       // #7759
       {R"smi([CH-]1[C@H]2C[C@H](C2)[C@@]12COC2)smi", false, true},      // #7759
-      {R"smi([O-]C1=C2C[C@H](C2)[C@@]12CC2)smi", false, false},         // #7759
+      {R"smi([O-]C1=C2C[C@H](C2)[C@@]12CC2)smi", false, true},          // #7759
       {R"smi(O=C1[C@H]2C[C-](C2)[C@@]12CC2)smi", false, true},          // #7759
       {R"smi([O-][C@]12C[C@H](C1)[C@@]1(CC1)C2)smi", false, true},      // #7759
       {R"smi([CH2-][C@]12C[C@H](C1)[C@]1(CC1)C2)smi", false, true},     // #7759
diff --git a/Code/GraphMol/catch_chirality.cpp b/Code/GraphMol/catch_chirality.cpp
index 05439052b..6f298a0e7 100644
--- a/Code/GraphMol/catch_chirality.cpp
+++ b/Code/GraphMol/catch_chirality.cpp
@@ -1251,6 +1251,17 @@ TEST_CASE("ring stereo finding is overly aggressive", "[chirality][bug]") {
         Chirality::findPotentialStereo(*mol, cleanIt, flagPossible);
     CHECK(stereoInfo.size() == 2);
   }
+  SECTION("bad ring chirality due to pair being in 2 rings") {
+    // from canonicalization watch test.
+
+    auto mol = "[O-]C1=C2C[C@H](C2)[C@@]12CC2"_smiles;
+    REQUIRE(mol);
+    bool cleanIt = true;
+    bool flagPossible = true;
+    auto stereoInfo =
+        Chirality::findPotentialStereo(*mol, cleanIt, flagPossible);
+    CHECK(stereoInfo.size() == 0);
+  }
   SECTION(
       "Removal of stereoatoms requires removing CIS/TRANS when using legacy stereo") {
     UseLegacyStereoPerceptionFixture reset_stereo_perception(false);