diff --git a/src/java/org/apache/cassandra/index/sai/plan/Operation.java b/src/java/org/apache/cassandra/index/sai/plan/Operation.java
index 111c014946c8..71cd781def91 100644
--- a/src/java/org/apache/cassandra/index/sai/plan/Operation.java
+++ b/src/java/org/apache/cassandra/index/sai/plan/Operation.java
@@ -99,7 +99,32 @@ protected static ListMultimap<ColumnMetadata, Expression> analyzeGroup(QueryCont
                 // if there is no EQ operations and NOT_EQ is met or a single NOT_EQ expression present,
                 // in such case we know exactly that there would be no more EQ/RANGE expressions for given column
                 // since NOT_EQ has the lowest priority.
-                boolean isMultiExpression = false;
+                boolean isMultiExpression = columnIsMultiExpression.getOrDefault(e.column(), Boolean.FALSE);
+                switch (e.operator())
+                {
+                    // case BM25: leave it at the default of `false`
+                    case EQ:
+                        // EQ operator will always be a multiple expression because it is being used by map entries
+                        isMultiExpression = indexContext.isNonFrozenCollection();
+
+                        // EQ wil behave like ANALYZER_MATCHES for analyzed columns if the analyzer supports EQ queries
+                        isMultiExpression |= indexContext.isAnalyzed() && analyzerFactory.supportsEquals();
+                        break;
+                    case CONTAINS:
+                    case CONTAINS_KEY:
+                    case NOT_CONTAINS:
+                    case NOT_CONTAINS_KEY:
+                    case LIKE_PREFIX:
+                    case LIKE_MATCHES:
+                    case ANALYZER_MATCHES:
+                        isMultiExpression = true;
+                        break;
+                    case NEQ:
+                        // NEQ operator will always be a multiple expression if it is the only operator
+                        // (e.g. multiple NEQ expressions)
+                        isMultiExpression = isMultiExpression || perColumn.isEmpty();
+                        break;
+                }
                 columnIsMultiExpression.put(e.column(), isMultiExpression);
 
                 if (isMultiExpression)