diff --git a/spring-data-mongodb/src/main/java/org/springframework/data/mongodb/core/query/MongoRegexCreator.java b/spring-data-mongodb/src/main/java/org/springframework/data/mongodb/core/query/MongoRegexCreator.java
index 9a97f1df3..898861cef 100644
--- a/spring-data-mongodb/src/main/java/org/springframework/data/mongodb/core/query/MongoRegexCreator.java
+++ b/spring-data-mongodb/src/main/java/org/springframework/data/mongodb/core/query/MongoRegexCreator.java
@@ -107,7 +107,9 @@ public enum MongoRegexCreator {
 	 * @param source
 	 * @return
 	 * @since 2.2.14
+	 * @deprecated since 3.4.13
 	 */
+	@Deprecated
 	public Object toCaseInsensitiveMatch(Object source) {
 		return source instanceof String ? new BsonRegularExpression(Pattern.quote((String) source), "i") : source;
 	}
diff --git a/spring-data-mongodb/src/main/java/org/springframework/data/mongodb/repository/query/MongoQueryCreator.java b/spring-data-mongodb/src/main/java/org/springframework/data/mongodb/repository/query/MongoQueryCreator.java
index 3838fdf68..d5747b801 100644
--- a/spring-data-mongodb/src/main/java/org/springframework/data/mongodb/repository/query/MongoQueryCreator.java
+++ b/spring-data-mongodb/src/main/java/org/springframework/data/mongodb/repository/query/MongoQueryCreator.java
@@ -25,7 +25,7 @@ import java.util.regex.Pattern;
 
 import org.apache.commons.logging.Log;
 import org.apache.commons.logging.LogFactory;
-
+import org.bson.BsonRegularExpression;
 import org.springframework.data.domain.Range;
 import org.springframework.data.domain.Range.Bound;
 import org.springframework.data.domain.Sort;
@@ -406,7 +406,18 @@ class MongoQueryCreator extends AbstractQueryCreator<Query, Criteria> {
 
 		Streamable<?> streamable = asStreamable(iterator.next());
 		if (!isSimpleComparisionPossible(part)) {
-			streamable = streamable.map(MongoRegexCreator.INSTANCE::toCaseInsensitiveMatch);
+
+			MatchMode matchMode = toMatchMode(part.getType());
+			String regexOptions = toRegexOptions(part);
+
+			streamable = streamable.map(it -> {
+				if (it instanceof String) {
+
+					return new BsonRegularExpression(MongoRegexCreator.INSTANCE.toRegularExpression((String) it, matchMode),
+							regexOptions);
+				}
+				return it;
+			});
 		}
 
 		return streamable.toList();
@@ -498,6 +509,7 @@ class MongoQueryCreator extends AbstractQueryCreator<Query, Criteria> {
 				return MatchMode.REGEX;
 			case NEGATING_SIMPLE_PROPERTY:
 			case SIMPLE_PROPERTY:
+			case IN:
 				return MatchMode.EXACT;
 			default:
 				return MatchMode.DEFAULT;
diff --git a/spring-data-mongodb/src/test/java/org/springframework/data/mongodb/repository/AbstractPersonRepositoryIntegrationTests.java b/spring-data-mongodb/src/test/java/org/springframework/data/mongodb/repository/AbstractPersonRepositoryIntegrationTests.java
index 97dec780d..f1d5d09f4 100644
--- a/spring-data-mongodb/src/test/java/org/springframework/data/mongodb/repository/AbstractPersonRepositoryIntegrationTests.java
+++ b/spring-data-mongodb/src/test/java/org/springframework/data/mongodb/repository/AbstractPersonRepositoryIntegrationTests.java
@@ -1451,9 +1451,16 @@ public abstract class AbstractPersonRepositoryIntegrationTests implements Dirtie
 		assertThat(result.get(0).getId().equals(bart.getId()));
 	}
 
-	@Test // GH-3395
+	@Test // GH-3395, GH-4404
 	void caseInSensitiveInClause() {
+
 		assertThat(repository.findByLastnameIgnoreCaseIn("bEAuFoRd", "maTTheWs")).hasSize(3);
+
+		repository.save(new Person("the-first", "The First"));
+		repository.save(new Person("the-first-one", "The First One"));
+		repository.save(new Person("the-second", "The Second"));
+
+		assertThat(repository.findByLastnameIgnoreCaseIn("tHE fIRsT")).hasSize(1);
 	}
 
 	@Test // GH-3395
diff --git a/spring-data-mongodb/src/test/java/org/springframework/data/mongodb/repository/query/MongoQueryCreatorUnitTests.java b/spring-data-mongodb/src/test/java/org/springframework/data/mongodb/repository/query/MongoQueryCreatorUnitTests.java
index efb20a86e..85484e01a 100644
--- a/spring-data-mongodb/src/test/java/org/springframework/data/mongodb/repository/query/MongoQueryCreatorUnitTests.java
+++ b/spring-data-mongodb/src/test/java/org/springframework/data/mongodb/repository/query/MongoQueryCreatorUnitTests.java
@@ -25,6 +25,7 @@ import java.lang.reflect.Method;
 import java.util.List;
 import java.util.regex.Pattern;
 
+import org.bson.BsonRegularExpression;
 import org.bson.Document;
 import org.bson.types.ObjectId;
 import org.junit.jupiter.api.BeforeEach;
@@ -277,6 +278,17 @@ class MongoQueryCreatorUnitTests {
 		assertThat(query).isEqualTo(query(where("firstName").regex("^dave$", "i")));
 	}
 
+	@Test // GH-4404
+	void createsQueryWithFindByInClauseHavingIgnoreCaseCorrectly() {
+
+		PartTree tree = new PartTree("findAllByFirstNameInIgnoreCase", Person.class);
+		MongoQueryCreator creator = new MongoQueryCreator(tree, getAccessor(converter, List.of("da've", "carter")), context);
+
+		Query query = creator.createQuery();
+		assertThat(query).isEqualTo(query(where("firstName")
+				.in(List.of(new BsonRegularExpression("^\\Qda've\\E$", "i"), new BsonRegularExpression("^carter$", "i")))));
+	}
+
 	@Test // DATAMONGO-770
 	void createsQueryWithFindByNotIgnoreCaseCorrectly() {