diff --git a/headless-services/commons/commons-util/src/main/java/org/springframework/ide/vscode/commons/util/EnumValueParser.java b/headless-services/commons/commons-util/src/main/java/org/springframework/ide/vscode/commons/util/EnumValueParser.java
index d8ba8c984c..d7f08dedf0 100644
--- a/headless-services/commons/commons-util/src/main/java/org/springframework/ide/vscode/commons/util/EnumValueParser.java
+++ b/headless-services/commons/commons-util/src/main/java/org/springframework/ide/vscode/commons/util/EnumValueParser.java
@@ -11,6 +11,7 @@
 package org.springframework.ide.vscode.commons.util;
 
 import java.util.Collection;
+import java.util.Collections;
 import java.util.TreeSet;
 import java.util.concurrent.Callable;
 import java.util.function.Supplier;
@@ -78,6 +79,11 @@ public Object parse(String str) throws Exception {
 			throw errorOnParse(createErrorMessage(str, values.getElements()));
 		}
 	}
+	
+	protected final Collection<String> getAllKnownValues() {
+		PartialCollection<String> partialCollection = this.values.get();
+		return partialCollection == null ? Collections.emptyList() : this.values.get().getElements();
+	}
 
 	protected boolean hasMatchingValue(String str, Collection<String> values) {
 		return values.contains(str);
diff --git a/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/metadata/types/TypeUtil.java b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/metadata/types/TypeUtil.java
index 354a13888e..fe9d3a87b4 100644
--- a/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/metadata/types/TypeUtil.java
+++ b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/metadata/types/TypeUtil.java
@@ -44,6 +44,7 @@
 import org.springframework.ide.vscode.boot.metadata.hints.StsValueHint;
 import org.springframework.ide.vscode.boot.metadata.util.DeprecationUtil;
 import org.springframework.ide.vscode.boot.metadata.util.PropertyDocUtils;
+import org.springframework.ide.vscode.boot.properties.reconcile.BootEnumValueParser;
 import org.springframework.ide.vscode.commons.java.Flags;
 import org.springframework.ide.vscode.commons.java.IField;
 import org.springframework.ide.vscode.commons.java.IJavaElement;
@@ -55,7 +56,6 @@
 import org.springframework.ide.vscode.commons.util.ArrayUtils;
 import org.springframework.ide.vscode.commons.util.Assert;
 import org.springframework.ide.vscode.commons.util.CollectionUtil;
-import org.springframework.ide.vscode.commons.util.EnumValueParser;
 import org.springframework.ide.vscode.commons.util.LazyProvider;
 import org.springframework.ide.vscode.commons.util.MimeTypes;
 import org.springframework.ide.vscode.commons.util.Renderables;
@@ -272,7 +272,7 @@ public ValueParser getValueParser(Type type) {
 				//Note, technically if 'enumValues is empty array' this means something different
 				// from when it is null. An empty array means a type that has no values, so
 				// assigning anything to it is an error.
-				return new EnumValueParser(niceTypeName(type), getBareValues(enumValues));
+				return new BootEnumValueParser(niceTypeName(type), getBareValues(enumValues));
 			}
 			if (isMap(type)) {
 				//Trying to parse map types from scalars is not possible. Thus we
diff --git a/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/properties/reconcile/BootEnumValueParser.java b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/properties/reconcile/BootEnumValueParser.java
new file mode 100644
index 0000000000..bc9c901a2e
--- /dev/null
+++ b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/properties/reconcile/BootEnumValueParser.java
@@ -0,0 +1,59 @@
+/*******************************************************************************
+ * Copyright (c) 2025 Broadcom, Inc.
+ * All rights reserved. This program and the accompanying materials
+ * are made available under the terms of the Eclipse Public License v1.0
+ * which accompanies this distribution, and is available at
+ * https://www.eclipse.org/legal/epl-v10.html
+ *
+ * Contributors:
+ *     Broadcom, Inc. - initial API and implementation
+ *******************************************************************************/
+package org.springframework.ide.vscode.boot.properties.reconcile;
+
+import java.util.Arrays;
+import java.util.Set;
+import java.util.stream.Collectors;
+
+import org.springframework.ide.vscode.commons.util.EnumValueParser;
+import org.springframework.ide.vscode.commons.util.StringUtil;
+
+/**
+ * Boot property values allow relaxed parsing via canonical names. 
+ * 
+ * @author Alex Boyko
+ */
+public class BootEnumValueParser extends EnumValueParser {
+	
+	private Set<String> canonicalValues;
+	
+	private static String getCanonicalName(String name) {
+		StringBuilder canonicalName = new StringBuilder(name.length());
+		name.chars()
+			.filter(Character::isLetterOrDigit)
+			.map(Character::toLowerCase)
+			.forEach((c) -> canonicalName.append((char) c));
+		return canonicalName.toString();
+	}
+
+	public BootEnumValueParser(String typeName, String[] values) {
+		super(typeName, values);
+		this.canonicalValues = Arrays.stream(values).map(BootEnumValueParser::getCanonicalName).collect(Collectors.toSet());
+	}
+
+	@Override
+	public Object parse(String str) throws Exception {
+		// IMPORTANT: check the text FIRST before fetching values
+		// from the hints provider, as the hints provider may be expensive when
+		// resolving values
+		if (!StringUtil.hasText(str)) {
+			throw errorOnBlank(createBlankTextErrorMessage());
+		}
+
+		if (canonicalValues.contains(getCanonicalName(str))) {
+			return str;
+		} else {
+			throw errorOnParse(createErrorMessage(str, getAllKnownValues()));
+		}
+	}
+
+}
diff --git a/headless-services/spring-boot-language-server/src/test/java/org/springframework/ide/vscode/boot/test/ApplicationYamlEditorTest.java b/headless-services/spring-boot-language-server/src/test/java/org/springframework/ide/vscode/boot/test/ApplicationYamlEditorTest.java
index 69aa34d43d..414b7068b5 100644
--- a/headless-services/spring-boot-language-server/src/test/java/org/springframework/ide/vscode/boot/test/ApplicationYamlEditorTest.java
+++ b/headless-services/spring-boot-language-server/src/test/java/org/springframework/ide/vscode/boot/test/ApplicationYamlEditorTest.java
@@ -5014,6 +5014,7 @@ private void doCollectionOfEnumReconcileTest(String collectionType) throws Excep
 				"my:\n" +
 				"  colors:\n" +
 				"  - red\n" +
+				"  - r-e-d\n" + // Canonical name is "red" from "r-e-d" hence it is okay in Boot as well 
 				"  - green\n" +
 				"  - BLUE\n" +
 				"  - not-a-color\n"