diff --git a/Code/GraphMol/Chirality.cpp b/Code/GraphMol/Chirality.cpp
index e3ca34cf0..abdeb250d 100644
--- a/Code/GraphMol/Chirality.cpp
+++ b/Code/GraphMol/Chirality.cpp
@@ -1450,7 +1450,8 @@ void findAtomNeighborsHelper(const ROMol &mol, const Atom *atom,
 }
 
 // conditions for an atom to be a candidate for ring stereochem:
-//   1) two non-ring neighbors that have different ranks
+//   1) two non-ring neighbors that have different ranks (the ring neighbors
+//      will have the same rank)
 //   2) one non-ring neighbor and two ring neighbors (the ring neighbors will
 //      have the same rank)
 //   3) four ring neighbors with three different ranks
@@ -1462,7 +1463,6 @@ bool atomIsCandidateForRingStereochem(
     const std::vector<unsigned int> &atomRanks) {
   PRECONDITION(atom, "bad atom");
   bool res = false;
-  std::set<unsigned int> nbrRanks;
   if (!atom->getPropIfPresent(common_properties::_ringStereochemCand, res)) {
     const RingInfo *ringInfo = mol.getRingInfo();
     if (ringInfo->isInitialized() && ringInfo->numAtomRings(atom->getIdx())) {
@@ -1477,33 +1477,35 @@ bool atomIsCandidateForRingStereochem(
       }
       std::vector<const Atom *> nonRingNbrs;
       std::vector<const Atom *> ringNbrs;
+      std::set<unsigned int> ringNbrRanks;
       for (const auto bond : mol.atomBonds(atom)) {
         if (!ringInfo->numBondRings(bond->getIdx())) {
           nonRingNbrs.push_back(bond->getOtherAtom(atom));
         } else {
           const Atom *nbr = bond->getOtherAtom(atom);
           ringNbrs.push_back(nbr);
-          nbrRanks.insert(atomRanks[nbr->getIdx()]);
+          ringNbrRanks.insert(atomRanks[nbr->getIdx()]);
         }
       }
-      // std::cerr << "!!!! " << atom->getIdx() << " " << nbrRanks.size() << " "
+      // std::cerr << "!!!! " << atom->getIdx() << " " << ringNbrRanks.size() << " "
       //           << ringNbrs.size() << " " << nonRingNbrs.size() << std::endl;
       switch (nonRingNbrs.size()) {
         case 2:
-          // they have to be different
+          // the ranks of the non ring neighbors must be different AND
+          // the ranks of the ring neighbors must be the same (see issue #8956)
           res = atomRanks[nonRingNbrs[0]->getIdx()] !=
                 atomRanks[nonRingNbrs[1]->getIdx()];
-
+          res &= (ringNbrs.size() != ringNbrRanks.size());
           break;
         case 1:
-          if (ringNbrs.size() > nbrRanks.size()) {
+          if (ringNbrs.size() > ringNbrRanks.size()) {
             res = true;
           }
           break;
         case 0:
-          if (ringNbrs.size() == 4 && nbrRanks.size() == 3) {
+          if (ringNbrs.size() == 4 && ringNbrRanks.size() == 3) {
             res = true;
-          } else if (ringNbrs.size() == 3 && nbrRanks.size() == 2) {
+          } else if (ringNbrs.size() == 3 && ringNbrRanks.size() == 2) {
             res = true;
           } else {
             res = false;
diff --git a/Code/GraphMol/catch_chirality.cpp b/Code/GraphMol/catch_chirality.cpp
index 421cdd788..05439052b 100644
--- a/Code/GraphMol/catch_chirality.cpp
+++ b/Code/GraphMol/catch_chirality.cpp
@@ -6348,6 +6348,28 @@ TEST_CASE("extra ring stereo with new stereo perception") {
       CHECK(atm->hasProp(common_properties::_ringStereoAtoms));
     }
   }
+  SECTION("#8956 ensure ring stereochemistry is not inverted on round trip") {
+    auto useLegacy = GENERATE(true, false);
+    CAPTURE(useLegacy);
+    UseLegacyStereoPerceptionFixture fx(useLegacy);
+    auto [smi1, smi2] = GENERATE(
+        std::make_pair("CC[C@]1(C)CCC[C@](C)(O)C1",
+                       "CC[C@@]1(C)CCC[C@@](C)(O)C1"),
+        std::make_pair("C[C@H]1CCC[C@](C)(O)C1", "C[C@@H]1CCC[C@@](C)(O)C1"));
+    auto m1 = v2::SmilesParse::MolFromSmiles(smi1);
+    REQUIRE(m1);
+    auto m2 = v2::SmilesParse::MolFromSmiles(smi2);
+    REQUIRE(m2);
+
+    MolOps::assignStereochemistry(*m1, true, true, true);
+    MolOps::assignStereochemistry(*m2, true, true, true);
+
+    auto roundtrip1 = MolToSmiles(*m1);
+    auto roundtrip2 = MolToSmiles(*m2);
+    CHECK(roundtrip1 == smi1);
+    CHECK(roundtrip2 == smi2);
+    CHECK(roundtrip2 != roundtrip1);
+  }
 }
 TEST_CASE("ring stereo basics with new stereo") {
   UseLegacyStereoPerceptionFixture reset_stereo_perception(false);