diff --git a/ketcher-autotests/tests/Macromolecule-editor/Macro-Micro-Switcher/macro-micro-switcher.spec.ts-snapshots/Macro-Micro-Switcher-Check-that-macromolecule--716dd-romode-are-represented-as-S-Groups-with-bonds-1-chromium-linux.png b/ketcher-autotests/tests/Macromolecule-editor/Macro-Micro-Switcher/macro-micro-switcher.spec.ts-snapshots/Macro-Micro-Switcher-Check-that-macromolecule--716dd-romode-are-represented-as-S-Groups-with-bonds-1-chromium-linux.png
index ccff6560da..fda8ccc2c2 100755
Binary files a/ketcher-autotests/tests/Macromolecule-editor/Macro-Micro-Switcher/macro-micro-switcher.spec.ts-snapshots/Macro-Micro-Switcher-Check-that-macromolecule--716dd-romode-are-represented-as-S-Groups-with-bonds-1-chromium-linux.png and b/ketcher-autotests/tests/Macromolecule-editor/Macro-Micro-Switcher/macro-micro-switcher.spec.ts-snapshots/Macro-Micro-Switcher-Check-that-macromolecule--716dd-romode-are-represented-as-S-Groups-with-bonds-1-chromium-linux.png differ
diff --git a/ketcher-autotests/tests/Macromolecule-editor/Macro-Micro-Switcher/macro-micro-switcher.spec.ts-snapshots/Verify-that-Expand-monomer-does-not-break-cyclic-structures-when-the-ring-is-expanded-2-chromium-linux.png b/ketcher-autotests/tests/Macromolecule-editor/Macro-Micro-Switcher/macro-micro-switcher.spec.ts-snapshots/Verify-that-Expand-monomer-does-not-break-cyclic-structures-when-the-ring-is-expanded-2-chromium-linux.png
index 5f0ddba257..2be00a360b 100644
Binary files a/ketcher-autotests/tests/Macromolecule-editor/Macro-Micro-Switcher/macro-micro-switcher.spec.ts-snapshots/Verify-that-Expand-monomer-does-not-break-cyclic-structures-when-the-ring-is-expanded-2-chromium-linux.png and b/ketcher-autotests/tests/Macromolecule-editor/Macro-Micro-Switcher/macro-micro-switcher.spec.ts-snapshots/Verify-that-Expand-monomer-does-not-break-cyclic-structures-when-the-ring-is-expanded-2-chromium-linux.png differ
diff --git a/packages/ketcher-core/src/application/editor/actions/sgroup.ts b/packages/ketcher-core/src/application/editor/actions/sgroup.ts
index 3ad7c632ee..0873f95c11 100644
--- a/packages/ketcher-core/src/application/editor/actions/sgroup.ts
+++ b/packages/ketcher-core/src/application/editor/actions/sgroup.ts
@@ -196,7 +196,10 @@ export function setExpandMonomerSGroup(
       atom.a.neighbors.forEach((halfBondId) => {
         const neighborAtomId =
           restruct.molecule?.halfBonds?.get(halfBondId)?.end;
-        if (!neighborAtomId || sGroupAtoms.includes(neighborAtomId)) {
+        if (
+          neighborAtomId === undefined ||
+          sGroupAtoms.includes(neighborAtomId)
+        ) {
           return;
         }
 
diff --git a/packages/ketcher-core/src/domain/entities/monomerMicromolecule.ts b/packages/ketcher-core/src/domain/entities/monomerMicromolecule.ts
index 81bd9be656..5b96850d2a 100644
--- a/packages/ketcher-core/src/domain/entities/monomerMicromolecule.ts
+++ b/packages/ketcher-core/src/domain/entities/monomerMicromolecule.ts
@@ -24,6 +24,10 @@ export class MonomerMicromolecule extends SGroup {
     this.data.attached = false;
   }
 
+  public get isMonomer() {
+    return true;
+  }
+
   public override getContractedPosition(struct: Struct) {
     assert(this.pp);
     const sgroupContractedPosition = super.getContractedPosition(struct);
diff --git a/packages/ketcher-core/src/domain/entities/sgroup.ts b/packages/ketcher-core/src/domain/entities/sgroup.ts
index b04ff05186..0ae471608e 100644
--- a/packages/ketcher-core/src/domain/entities/sgroup.ts
+++ b/packages/ketcher-core/src/domain/entities/sgroup.ts
@@ -368,6 +368,10 @@ export class SGroup {
     return this.type === SGroup.TYPES.SUP && !this.data.name;
   }
 
+  public get isMonomer() {
+    return false;
+  }
+
   static getOffset(sgroup: SGroup): null | Vec2 {
     if (!sgroup?.pp || !sgroup.bracketBox) return null;
     return Vec2.diff(sgroup.pp, sgroup.bracketBox.p1);
@@ -504,7 +508,8 @@ export class SGroup {
     const crossBonds = crossBondsPerAtom
       ? Object.values(crossBondsPerAtom).flat()
       : null;
-    if (!crossBonds || crossBonds.length !== 2) {
+    // TODO: Overall cross bonds logic seems unclear and not-correct for s groups in general leading to tilted hover plate
+    if (sGroup.isMonomer || !crossBonds || crossBonds.length !== 2) {
       sGroup.bracketDirection = new Vec2(1, 0);
     } else {
       const p1 = mol.bonds.get(crossBonds[0]).getCenter(mol);
diff --git a/packages/ketcher-react/src/script/ui/views/components/ContextMenu/menuItems/MacromoleculeMenuItems.tsx b/packages/ketcher-react/src/script/ui/views/components/ContextMenu/menuItems/MacromoleculeMenuItems.tsx
index dd70e11923..6a70b06866 100644
--- a/packages/ketcher-react/src/script/ui/views/components/ContextMenu/menuItems/MacromoleculeMenuItems.tsx
+++ b/packages/ketcher-react/src/script/ui/views/components/ContextMenu/menuItems/MacromoleculeMenuItems.tsx
@@ -10,6 +10,17 @@ const MacromoleculeMenuItems = (
 ) => {
   const [action, hidden] = useMonomerExpansionHandlers();
 
+  const multipleMonomersSelected =
+    props?.propsFromTrigger?.functionalGroups &&
+    props.propsFromTrigger.functionalGroups.length > 1;
+
+  const expandText = multipleMonomersSelected
+    ? 'Expand monomers'
+    : 'Expand monomer';
+  const collapseText = multipleMonomersSelected
+    ? 'Collapse monomers'
+    : 'Collapse monomer';
+
   return (
     <>
       <Item
@@ -17,14 +28,14 @@ const MacromoleculeMenuItems = (
         hidden={(params) => hidden(params, true)}
         onClick={(params) => action(params, true)}
       >
-        Expand monomer
+        {expandText}
       </Item>
       <Item
         {...props}
         hidden={(params) => hidden(params, false)}
         onClick={(params) => action(params, false)}
       >
-        Collapse monomer
+        {collapseText}
       </Item>
     </>
   );