diff --git a/hibernate-community-dialects/src/main/java/org/hibernate/community/dialect/MariaDBLegacyDialect.java b/hibernate-community-dialects/src/main/java/org/hibernate/community/dialect/MariaDBLegacyDialect.java
index 6f5d4e6e702e..f9ef9ec3ca50 100644
--- a/hibernate-community-dialects/src/main/java/org/hibernate/community/dialect/MariaDBLegacyDialect.java
+++ b/hibernate-community-dialects/src/main/java/org/hibernate/community/dialect/MariaDBLegacyDialect.java
@@ -216,6 +216,11 @@ public boolean supportsColumnCheck() {
 		return getVersion().isSameOrAfter( 10, 2 );
 	}
 
+	@Override
+	public boolean supportsNamedColumnCheck() {
+		return false;
+	}
+
 	@Override
 	public boolean doesRoundTemporalOnOverflow() {
 		// See https://jira.mariadb.org/browse/MDEV-16991
diff --git a/hibernate-core/src/main/java/org/hibernate/boot/model/internal/AnnotatedColumn.java b/hibernate-core/src/main/java/org/hibernate/boot/model/internal/AnnotatedColumn.java
index f0385ea2ab6f..6bf98fddaf22 100644
--- a/hibernate-core/src/main/java/org/hibernate/boot/model/internal/AnnotatedColumn.java
+++ b/hibernate-core/src/main/java/org/hibernate/boot/model/internal/AnnotatedColumn.java
@@ -967,7 +967,7 @@ void applyCheckConstraints(jakarta.persistence.CheckConstraint[] checkConstraint
 		if ( isNotEmpty( checkConstraintAnnotationUsages ) ) {
 			for ( jakarta.persistence.CheckConstraint checkConstraintAnnotationUsage : checkConstraintAnnotationUsages ) {
 				addCheckConstraint(
-						checkConstraintAnnotationUsage.name(),
+						nullIfEmpty( checkConstraintAnnotationUsage.name() ),
 						checkConstraintAnnotationUsage.constraint(),
 						checkConstraintAnnotationUsage.options()
 				);
@@ -983,7 +983,7 @@ void applyCheckConstraint(PropertyData inferredData, int length) {
 			if ( checksAnn != null ) {
 				final Check[] checkAnns = checksAnn.value();
 				for ( Check checkAnn : checkAnns ) {
-					addCheckConstraint( checkAnn.name(), checkAnn.constraints() );
+					addCheckConstraint( nullIfEmpty( checkAnn.name() ), checkAnn.constraints() );
 				}
 			}
 			else {
diff --git a/hibernate-core/src/main/java/org/hibernate/boot/model/internal/TableBinder.java b/hibernate-core/src/main/java/org/hibernate/boot/model/internal/TableBinder.java
index ed807176d6b2..8392cf29716a 100644
--- a/hibernate-core/src/main/java/org/hibernate/boot/model/internal/TableBinder.java
+++ b/hibernate-core/src/main/java/org/hibernate/boot/model/internal/TableBinder.java
@@ -44,6 +44,7 @@
 import static org.hibernate.internal.util.StringHelper.isNotEmpty;
 import static org.hibernate.internal.util.StringHelper.isQuoted;
 import static org.hibernate.internal.util.StringHelper.nullIfBlank;
+import static org.hibernate.internal.util.StringHelper.nullIfEmpty;
 import static org.hibernate.internal.util.StringHelper.unquote;
 import static org.hibernate.internal.util.collections.CollectionHelper.isNotEmpty;
 
@@ -896,7 +897,7 @@ static void addTableCheck(
 			for ( jakarta.persistence.CheckConstraint checkConstraintAnnotationUsage : checkConstraintAnnotationUsages ) {
 				table.addCheck(
 						new CheckConstraint(
-								checkConstraintAnnotationUsage.name(),
+								nullIfEmpty( checkConstraintAnnotationUsage.name() ),
 								checkConstraintAnnotationUsage.constraint(),
 								checkConstraintAnnotationUsage.options()
 						)
diff --git a/hibernate-core/src/main/java/org/hibernate/dialect/Dialect.java b/hibernate-core/src/main/java/org/hibernate/dialect/Dialect.java
index c6f14ad203d9..36a22063575a 100644
--- a/hibernate-core/src/main/java/org/hibernate/dialect/Dialect.java
+++ b/hibernate-core/src/main/java/org/hibernate/dialect/Dialect.java
@@ -4186,6 +4186,16 @@ public boolean supportsColumnCheck() {
 		return true;
 	}
 
+	/**
+	 * Does this dialect support named column-level check constraints?
+	 *
+	 * @return True if named column-level {@code check} constraints are supported;
+	 *         false otherwise.
+	 */
+	public boolean supportsNamedColumnCheck() {
+		return supportsColumnCheck();
+	}
+
 	/**
 	 * Does this dialect support table-level check constraints?
 	 *
diff --git a/hibernate-core/src/main/java/org/hibernate/dialect/MariaDBDialect.java b/hibernate-core/src/main/java/org/hibernate/dialect/MariaDBDialect.java
index e2527fa8193e..cbe31addc501 100644
--- a/hibernate-core/src/main/java/org/hibernate/dialect/MariaDBDialect.java
+++ b/hibernate-core/src/main/java/org/hibernate/dialect/MariaDBDialect.java
@@ -245,6 +245,11 @@ public boolean supportsColumnCheck() {
 		return true;
 	}
 
+	@Override
+	public boolean supportsNamedColumnCheck() {
+		return false;
+	}
+
 	@Override
 	public boolean doesRoundTemporalOnOverflow() {
 		// See https://jira.mariadb.org/browse/MDEV-16991
diff --git a/hibernate-core/src/main/java/org/hibernate/tool/schema/internal/ColumnDefinitions.java b/hibernate-core/src/main/java/org/hibernate/tool/schema/internal/ColumnDefinitions.java
index 3130e3ed894f..c68bb8b359d7 100644
--- a/hibernate-core/src/main/java/org/hibernate/tool/schema/internal/ColumnDefinitions.java
+++ b/hibernate-core/src/main/java/org/hibernate/tool/schema/internal/ColumnDefinitions.java
@@ -144,34 +144,41 @@ private static void appendConstraints(
 		}
 
 		if ( dialect.supportsColumnCheck() ) {
-			// some databases (Maria, SQL Server) don't like multiple 'check' clauses
 			final List<CheckConstraint> checkConstraints = column.getCheckConstraints();
-			long anonConstraints = checkConstraints.stream().filter(CheckConstraint::isAnonymous).count();
-			if ( anonConstraints == 1 ) {
-				for ( CheckConstraint constraint : checkConstraints ) {
-					definition.append( constraint.constraintString( dialect ) );
+			boolean hasAnonymousConstraints = false;
+			for ( CheckConstraint constraint : checkConstraints ) {
+				if ( constraint.isAnonymous() ) {
+					if ( !hasAnonymousConstraints ) {
+						definition.append(" check (");
+						hasAnonymousConstraints = true;
+					}
+					else {
+						definition.append(" and ");
+					}
+					definition.append( constraint.getConstraintInParens() );
 				}
 			}
-			else {
-				boolean first = true;
+			if ( hasAnonymousConstraints ) {
+				definition.append( ')' );
+			}
+
+			if ( !dialect.supportsTableCheck() ) {
+				// When table check constraints are not supported, try to render all named constraints
 				for ( CheckConstraint constraint : checkConstraints ) {
-					if ( constraint.isAnonymous() ) {
-						if ( first ) {
-							definition.append(" check (");
-							first = false;
-						}
-						else {
-							definition.append(" and ");
-						}
-						definition.append( constraint.getConstraintInParens() );
+					if ( constraint.isNamed() ) {
+						definition.append( constraint.constraintString( dialect ) );
 					}
 				}
-				if ( !first ) {
-					definition.append(")");
-				}
+			}
+			else if ( !hasAnonymousConstraints && dialect.supportsNamedColumnCheck() ) {
+				// Otherwise only render the first named constraint as column constraint if there are no anonymous
+				// constraints and named column check constraint are supported, because some database don't like
+				// multiple check clauses.
+				// Note that the TableExporter will take care of named constraints then
 				for ( CheckConstraint constraint : checkConstraints ) {
 					if ( constraint.isNamed() ) {
 						definition.append( constraint.constraintString( dialect ) );
+						break;
 					}
 				}
 			}
diff --git a/hibernate-core/src/main/java/org/hibernate/tool/schema/internal/StandardTableExporter.java b/hibernate-core/src/main/java/org/hibernate/tool/schema/internal/StandardTableExporter.java
index 98358f28aab0..f597d840371e 100644
--- a/hibernate-core/src/main/java/org/hibernate/tool/schema/internal/StandardTableExporter.java
+++ b/hibernate-core/src/main/java/org/hibernate/tool/schema/internal/StandardTableExporter.java
@@ -197,37 +197,43 @@ protected void applyTableTypeString(StringBuilder buf) {
 
 	protected void applyTableCheck(Table table, StringBuilder buf) {
 		if ( dialect.supportsTableCheck() ) {
-			if ( !dialect.supportsColumnCheck() ) {
-				for ( Column column : table.getColumns() ) {
-					// some databases (Maria, SQL Server) don't like multiple 'check' clauses
-					final List<CheckConstraint> checkConstraints = column.getCheckConstraints();
-					long anonConstraints = checkConstraints.stream().filter( CheckConstraint::isAnonymous ).count();
-					if ( anonConstraints == 1 ) {
-						for ( CheckConstraint constraint : checkConstraints ) {
-							buf.append( "," ).append( constraint.constraintString( dialect ) );
-						}
-					}
-					else {
-						boolean first = true;
-						for ( CheckConstraint constraint : checkConstraints ) {
-							if ( constraint.isAnonymous() ) {
-								if ( first ) {
-									buf.append( "," ).append( " check (" );
-									first = false;
-								}
-								else {
-									buf.append( " and " );
-								}
-								buf.append( constraint.getConstraintInParens() );
+			for ( Column column : table.getColumns() ) {
+				final List<CheckConstraint> checkConstraints = column.getCheckConstraints();
+				boolean hasAnonymousConstraints = false;
+				if ( !dialect.supportsColumnCheck() ) {
+					for ( CheckConstraint constraint : checkConstraints ) {
+						if ( constraint.isAnonymous() ) {
+							if ( !hasAnonymousConstraints ) {
+								buf.append( ", check (" );
+								hasAnonymousConstraints = true;
+							}
+							else {
+								buf.append( " and " );
 							}
+							buf.append( constraint.getConstraintInParens() );
 						}
-						if ( !first ) {
-							buf.append( ")" );
+					}
+					if ( hasAnonymousConstraints ) {
+						buf.append( ')' );
+					}
+				}
+				else {
+					hasAnonymousConstraints = checkConstraints.stream().anyMatch( CheckConstraint::isAnonymous );
+				}
+
+				// Since some databases don't like when multiple check clauses appear for a colum definition,
+				// named constraints need to be hoisted to the table definition.
+				// Skip the first named constraint if the column has no anonymous constraints and the dialect
+				// supports named column check constraints, because ColumnDefinitions will render the first check
+				// constraint already.
+				boolean skipNextNamedConstraint = !hasAnonymousConstraints && dialect.supportsNamedColumnCheck();
+				for ( CheckConstraint constraint : checkConstraints ) {
+					if ( constraint.isNamed() ) {
+						if ( skipNextNamedConstraint ) {
+							skipNextNamedConstraint = false;
 						}
-						for ( CheckConstraint constraint : checkConstraints ) {
-							if ( constraint.isNamed() ) {
-								buf.append( constraint.constraintString( dialect ) );
-							}
+						else {
+							buf.append( ',' ).append( constraint.constraintString( dialect ) );
 						}
 					}
 				}