diff --git a/hibernate-core/src/main/java/org/hibernate/persister/entity/AbstractEntityPersister.java b/hibernate-core/src/main/java/org/hibernate/persister/entity/AbstractEntityPersister.java
index 27b9f5fa2f..6f5c38d615 100644
--- a/hibernate-core/src/main/java/org/hibernate/persister/entity/AbstractEntityPersister.java
+++ b/hibernate-core/src/main/java/org/hibernate/persister/entity/AbstractEntityPersister.java
@@ -3255,7 +3255,7 @@ public abstract class AbstractEntityPersister
 			Map<String, EntityNameUse> entityNameUses,
 			MappingMetamodelImplementor mappingMetamodel,
 			String alias) {
-		final InFragment frag = new InFragment();
+		final InFragment frag = new InFragment( false );
 		if ( isDiscriminatorFormula() ) {
 			frag.setFormula( alias, getDiscriminatorFormulaTemplate() );
 		}
diff --git a/hibernate-core/src/main/java/org/hibernate/sql/InFragment.java b/hibernate-core/src/main/java/org/hibernate/sql/InFragment.java
index d41a3cfd7d..6516705164 100644
--- a/hibernate-core/src/main/java/org/hibernate/sql/InFragment.java
+++ b/hibernate-core/src/main/java/org/hibernate/sql/InFragment.java
@@ -21,10 +21,15 @@ import org.hibernate.internal.util.StringHelper;
 @Internal
 public class InFragment {
 
+	public InFragment(boolean columnCanBeNull) {
+		this.columnCanBeNull = columnCanBeNull;
+	}
+
 	public static final String NULL = "null";
 	public static final String NOT_NULL = "not null";
 
 	protected String columnName;
+	protected boolean columnCanBeNull;
 	protected List<Object> values = new ArrayList<>();
 
 	/**
@@ -62,67 +67,80 @@ public class InFragment {
 	}
 
 	public String toFragmentString() {
-		if ( values.size() == 0 ) {
-			return "1=2";
-		}
+		final StringBuilder buf = new StringBuilder( values.size() * 5 );
 
-		StringBuilder buf = new StringBuilder( values.size() * 5 );
-
-		if ( values.size() == 1 ) {
-			Object value = values.get( 0 );
-			buf.append( columnName );
-
-			if ( NULL.equals( value ) ) {
-				buf.append( " is null" );
-			}
-			else {
-				if ( NOT_NULL.equals( value ) ) {
-					buf.append( " is not null" );
+		switch ( values.size() ) {
+			case 0: {
+				if ( columnCanBeNull ) {
+					return buf.append( "(1 = case when " )
+							.append( columnName )
+							.append(" is not null then 0 end)")
+							.toString();
 				}
 				else {
-					buf.append( '=' ).append( value );
+					return "0=1";
 				}
 			}
-			return buf.toString();
-		}
+			case 1: {
+				Object value = values.get( 0 );
+				buf.append( columnName );
 
-		boolean allowNull = false;
-
-		for ( Object value : values ) {
-			if ( NULL.equals( value ) ) {
-				allowNull = true;
-			}
-			else {
-				if ( NOT_NULL.equals( value ) ) {
-					throw new IllegalArgumentException( "not null makes no sense for in expression" );
+				if ( NULL.equals( value ) ) {
+					buf.append( " is null" );
 				}
+				else {
+					if ( NOT_NULL.equals( value ) ) {
+						buf.append( " is not null" );
+					}
+					else {
+						buf.append( '=' ).append( value );
+					}
+				}
+				return buf.toString();
+			}
+			default: {
+				boolean allowNull = false;
+
+				for ( Object value : values ) {
+					if ( NULL.equals( value ) ) {
+						allowNull = true;
+					}
+					else {
+						if ( NOT_NULL.equals( value ) ) {
+							throw new IllegalArgumentException( "not null makes no sense for in expression" );
+						}
+					}
+				}
+
+				if ( allowNull ) {
+					buf.append( '(' )
+							.append( columnName )
+							.append( " is null or " )
+							.append( columnName )
+							.append( " in (" );
+				}
+				else {
+					buf.append( columnName ).append( " in (" );
+				}
+
+				for ( Object value : values ) {
+					if ( !NULL.equals( value ) ) {
+						buf.append( value );
+						buf.append( ", " );
+					}
+				}
+
+				buf.setLength( buf.length() - 2 );
+
+				if ( allowNull ) {
+					buf.append( "))" );
+				}
+				else {
+					buf.append( ')' );
+				}
+
+				return buf.toString();
 			}
 		}
-
-		if ( allowNull ) {
-			buf.append( '(' ).append( columnName ).append( " is null or " ).append( columnName ).append( " in (" );
-		}
-		else {
-			buf.append( columnName ).append( " in (" );
-		}
-
-		for ( Object value : values ) {
-			if ( !NULL.equals( value ) ) {
-				buf.append( value );
-				buf.append( ", " );
-			}
-		}
-
-		buf.setLength( buf.length() - 2 );
-
-		if ( allowNull ) {
-			buf.append( "))" );
-		}
-		else {
-			buf.append( ')' );
-		}
-
-		return buf.toString();
-
 	}
 }
diff --git a/hibernate-core/src/main/java/org/hibernate/sql/ast/spi/AbstractSqlAstTranslator.java b/hibernate-core/src/main/java/org/hibernate/sql/ast/spi/AbstractSqlAstTranslator.java
index f881b27873..b870e64313 100644
--- a/hibernate-core/src/main/java/org/hibernate/sql/ast/spi/AbstractSqlAstTranslator.java
+++ b/hibernate-core/src/main/java/org/hibernate/sql/ast/spi/AbstractSqlAstTranslator.java
@@ -7603,7 +7603,7 @@ public abstract class AbstractSqlAstTranslator<T extends JdbcOperation> implemen
 	public void visitInListPredicate(InListPredicate inListPredicate) {
 		final List<Expression> listExpressions = inListPredicate.getListExpressions();
 		if ( listExpressions.isEmpty() ) {
-			appendSql( "1=" + ( inListPredicate.isNegated() ? "1" : "0" ) );
+			emptyInList( inListPredicate );
 			return;
 		}
 		Function<Expression, Expression> itemAccessor = Function.identity();
@@ -7710,6 +7710,16 @@ public abstract class AbstractSqlAstTranslator<T extends JdbcOperation> implemen
 		}
 	}
 
+	protected void emptyInList(InListPredicate inListPredicate) {
+		appendSql("(");
+		appendSql( inListPredicate.isNegated() ? "0" : "1" );
+		appendSql(" = case when ");
+		inListPredicate.getTestExpression().accept( this );
+		appendSql( " is not null then 0");
+//		dialect.appendBooleanValueString( this, inListPredicate.isNegated() );
+		appendSql(" end)");
+	}
+
 	private void appendInClauseSeparator(InListPredicate inListPredicate) {
 		appendSql( CLOSE_PARENTHESIS );
 		appendSql( inListPredicate.isNegated() ? " and " : " or " );