diff --git a/hibernate-core/src/main/java/org/hibernate/sql/Template.java b/hibernate-core/src/main/java/org/hibernate/sql/Template.java
index 05c5a78d028c..dc193c5d4e43 100644
--- a/hibernate-core/src/main/java/org/hibernate/sql/Template.java
+++ b/hibernate-core/src/main/java/org/hibernate/sql/Template.java
@@ -194,6 +194,8 @@ else if ( LITERAL_PREFIXES.contains( lcToken ) ) {
 						continue;
 					}
 					else if ( nextToken != null && Character.isWhitespace( nextToken.charAt( 0 ) ) ) {
+						final StringTokenizer lookahead = lookahead( sqlWhereString, symbols, tokens);
+						String lookaheadToken = lookahead.hasMoreTokens() ? lookahead.nextToken() : null;
 						final StringBuilder additionalTokens = new StringBuilder();
 						TimeZoneTokens possibleNextToken = null;
 						do {
@@ -201,15 +203,18 @@ else if ( nextToken != null && Character.isWhitespace( nextToken.charAt( 0 ) ) )
 									? TimeZoneTokens.getPossibleNextTokens( lcToken )
 									: possibleNextToken.nextToken();
 							do {
-								additionalTokens.append( nextToken );
-								hasMore = tokens.hasMoreTokens();
-								nextToken = tokens.nextToken();
-							} while ( nextToken != null && Character.isWhitespace( nextToken.charAt( 0 ) ) );
-						} while ( nextToken != null && possibleNextToken.isToken( nextToken ) );
-						if ( "'".equals( nextToken ) ) {
+								additionalTokens.append( lookaheadToken );
+								lookaheadToken = lookahead.hasMoreTokens() ? lookahead.nextToken() : null;
+							} while ( lookaheadToken != null && Character.isWhitespace( lookaheadToken.charAt( 0 ) ) );
+						} while ( lookaheadToken != null && possibleNextToken.isToken( lookaheadToken ) );
+						if ( "'".equals( lookaheadToken ) ) {
 							// Don't prefix a literal
 							result.append( token );
 							result.append( additionalTokens );
+							while (tokens.countTokens() > lookahead.countTokens()) {
+								hasMore = tokens.hasMoreTokens();
+								nextToken = hasMore ? tokens.nextToken() : null;
+							}
 							continue;
 						}
 						else {
@@ -401,6 +406,24 @@ else if ( inFromClause && ",".equals(lcToken) ) {
 		return result.toString();
 	}
 
+	/**
+	 * Clone the given token stream, returning a token stream which begins
+	 * from the next token.
+	 *
+	 * @param sql     the full SQL we are scanning
+	 * @param symbols the delimiter symbols
+	 * @param tokens  the current token stream
+	 * @return a cloned token stream
+	 */
+	private static StringTokenizer lookahead(String sql, String symbols, StringTokenizer tokens) {
+		final StringTokenizer lookahead =
+				new StringTokenizer( sql, symbols, true );
+		while ( lookahead.countTokens() > tokens.countTokens() + 1) {
+			lookahead.nextToken();
+		}
+		return lookahead;
+	}
+
 	private enum TimeZoneTokens {
 		NONE,
 		WITH,
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/joinsubquery/JoinSubqueryTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/joinsubquery/JoinSubqueryTest.java
new file mode 100644
index 000000000000..d54a7421cbd7
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/joinsubquery/JoinSubqueryTest.java
@@ -0,0 +1,129 @@
+/*
+ * Hibernate, Relational Persistence for Idiomatic Java
+ *
+ * License: GNU Lesser General Public License (LGPL), version 2.1 or later.
+ * See the lgpl.txt file in the root directory or <http://www.gnu.org/licenses/lgpl-2.1.html>.
+ */
+package org.hibernate.orm.test.joinsubquery;
+
+import jakarta.persistence.*;
+import org.hibernate.annotations.JoinColumnOrFormula;
+import org.hibernate.annotations.JoinFormula;
+import org.hibernate.testing.orm.junit.DomainModel;
+import org.hibernate.testing.orm.junit.JiraKey;
+import org.hibernate.testing.orm.junit.SessionFactory;
+import org.hibernate.testing.orm.junit.SessionFactoryScope;
+import org.junit.jupiter.api.BeforeAll;
+import org.junit.jupiter.api.Test;
+
+import java.io.Serializable;
+
+import static org.junit.jupiter.api.Assertions.assertNotNull;
+
+@DomainModel(annotatedClasses = {
+		JoinSubqueryTest.RecordItem.class,
+		JoinSubqueryTest.RecordType.class
+})
+@SessionFactory
+@JiraKey("HHH-19052")
+class JoinSubqueryTest {
+
+	@BeforeAll
+	static void setUp(SessionFactoryScope scope) throws Exception {
+		scope.inTransaction(session -> {
+			final var id = 1L;
+			final var typeId = 42L;
+			final var recordType = new RecordType(id, typeId);
+			session.persist(recordType);
+			final var item = new RecordItem(id, typeId, recordType);
+			session.persist(item);
+		});
+	}
+
+	@Test
+	void test(SessionFactoryScope scope) throws Exception {
+		scope.inSession(session -> {
+			final var item = session.get(RecordItem.class, 1L);
+			assertNotNull(item);
+		});
+	}
+
+	@Entity
+	@Table(name = "record_items")
+	public static class RecordItem implements Serializable {
+
+		@Id
+		protected Long id;
+
+		@Column(name = "type_id", insertable = false, updatable = false)
+		private Long typeId;
+
+		@ManyToOne(fetch = FetchType.EAGER)
+		@JoinColumnOrFormula(column = @JoinColumn(name = "type_id", referencedColumnName = "entity_id"))
+		@JoinColumnOrFormula(formula = @JoinFormula(value = "(SELECT x.id FROM record_types x WHERE x.entity_id = type_id)", referencedColumnName = "id"))
+		private RecordType type;
+
+		RecordItem() {
+		}
+
+		public RecordItem(Long id, Long typeId, RecordType type) {
+			this.id = id;
+			this.typeId = typeId;
+			this.type = type;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public Long getId() {
+			return this.id;
+		}
+
+		public Long getTypeId() {
+			return typeId;
+		}
+
+		public RecordType getType() {
+			return type;
+		}
+
+
+	}
+
+	@Entity
+	@Table(name = "record_types")
+	public static class RecordType implements Serializable {
+
+		@Id
+		protected Long id;
+
+		@Column(name = "entity_id")
+		private Long entityId;
+
+		RecordType() {
+		}
+
+		public RecordType(Long id, Long entityId) {
+			this.id = id;
+			this.entityId = entityId;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public Long getId() {
+			return this.id;
+		}
+
+		public Long getEntityId() {
+			return entityId;
+		}
+
+		public void setEntityId(Long entityId) {
+			this.entityId = entityId;
+		}
+
+	}
+}