diff --git a/rewrite-properties/src/main/java/org/openrewrite/properties/AddPropertyComment.java b/rewrite-properties/src/main/java/org/openrewrite/properties/AddPropertyComment.java
new file mode 100755
index 00000000000..73048521f1d
--- /dev/null
+++ b/rewrite-properties/src/main/java/org/openrewrite/properties/AddPropertyComment.java
@@ -0,0 +1,112 @@
+/*
+ * Copyright 2024 the original author or authors.
+ * <p>
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ * <p>
+ * https://www.apache.org/licenses/LICENSE-2.0
+ * <p>
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.openrewrite.properties;
+
+import lombok.EqualsAndHashCode;
+import lombok.Value;
+import org.jspecify.annotations.Nullable;
+import org.openrewrite.*;
+import org.openrewrite.internal.ListUtils;
+import org.openrewrite.marker.Markers;
+import org.openrewrite.properties.search.FindProperties;
+import org.openrewrite.properties.tree.Properties;
+
+import java.util.Arrays;
+import java.util.function.Function;
+
+import static org.openrewrite.Tree.randomId;
+
+@Value
+@EqualsAndHashCode(callSuper = false)
+public class AddPropertyComment extends Recipe {
+
+    @Option(displayName = "Property key",
+            description = "The name of the property to add comment.",
+            example = "management.metrics.binders")
+    String propertyKey;
+
+    @Option(example = "comment", displayName = "Comment",
+            description = "The comment to be added.")
+    String comment;
+
+    @Option(example = "true", displayName = "Comment out property",
+            description = "If true, property will be commented out.",
+            required = false)
+    @Nullable
+    Boolean commentOutProperty;
+
+    @Override
+    public String getDisplayName() {
+        return "Add comment before property key";
+    }
+
+    @Override
+    public String getDescription() {
+        return "Add a new comment before a property key if not already present, optionally commenting out the property.";
+    }
+
+    @Override
+    public TreeVisitor<?, ExecutionContext> getVisitor() {
+        PropertiesVisitor<ExecutionContext> propertiesVisitor = new PropertiesVisitor<ExecutionContext>() {
+            @Override
+            public Properties visitFile(Properties.File file, ExecutionContext ctx) {
+                Properties.File p = file.withContent(ListUtils.flatMap(file.getContent(), new Function<Properties.Content, Object>() {
+                            Properties.@Nullable Content previousContent = null;
+
+                            @Override
+                            public Object apply(Properties.Content c) {
+                                if (c instanceof Properties.Entry &&
+                                    ((Properties.Entry) c).getKey().equals(propertyKey) &&
+                                    !isCommentAlreadyPresent(previousContent, comment)) {
+                                    Properties.Comment commentContent = new Properties.Comment(
+                                            randomId(),
+                                            previousContent == null ? "" : "\n",
+                                            Markers.EMPTY,
+                                            Properties.Comment.Delimiter.HASH_TAG,
+                                            " " + comment.trim());
+                                    previousContent = c;
+                                    return Arrays.asList(commentContent, c.getPrefix().contains("\n") ?
+                                            c : c.withPrefix("\n" + c.getPrefix()));
+                                }
+                                previousContent = c;
+                                return c;
+                            }
+                        }
+                ));
+                return super.visitFile(p, ctx);
+            }
+
+            @Override
+            public Properties visitEntry(Properties.Entry entry, ExecutionContext ctx) {
+                if (Boolean.TRUE.equals(commentOutProperty) && entry.getKey().equals(propertyKey)) {
+                    return new Properties.Comment(
+                            randomId(),
+                            entry.getPrefix(),
+                            entry.getMarkers(),
+                            Properties.Comment.Delimiter.HASH_TAG,
+                            " " + entry.printTrimmed(getCursor()));
+                }
+                return super.visitEntry(entry, ctx);
+            }
+        };
+        return Preconditions.check(new FindProperties(propertyKey, false).getVisitor(), propertiesVisitor);
+    }
+
+    private boolean isCommentAlreadyPresent(Properties.@Nullable Content previousContent, String comment) {
+        return previousContent instanceof Properties.Comment &&
+               ((Properties.Comment) previousContent).getMessage().contains(comment.trim());
+    }
+}
diff --git a/rewrite-properties/src/test/java/org/openrewrite/properties/AddPropertyCommentTest.java b/rewrite-properties/src/test/java/org/openrewrite/properties/AddPropertyCommentTest.java
new file mode 100755
index 00000000000..05f643df5ce
--- /dev/null
+++ b/rewrite-properties/src/test/java/org/openrewrite/properties/AddPropertyCommentTest.java
@@ -0,0 +1,189 @@
+/*
+ * Copyright 2024 the original author or authors.
+ * <p>
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ * <p>
+ * https://www.apache.org/licenses/LICENSE-2.0
+ * <p>
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.openrewrite.properties;
+
+import org.junit.jupiter.api.Test;
+import org.openrewrite.DocumentExample;
+import org.openrewrite.test.RewriteTest;
+
+import static org.openrewrite.properties.Assertions.properties;
+
+class AddPropertyCommentTest implements RewriteTest {
+
+    @DocumentExample
+    @Test
+    void shouldAddCommentToFirstProperty() {
+        rewriteRun(
+          spec -> spec.recipe(new AddPropertyComment(
+            "management.metrics.enable.process.files",
+            "myComment",
+            false
+          )),
+          properties(
+            """
+              management.metrics.enable.process.files=true
+              yyy=true
+              """,
+            """
+              # myComment
+              management.metrics.enable.process.files=true
+              yyy=true
+              """
+          )
+        );
+    }
+
+    @Test
+    void shouldAddCommentToMiddleProperty() {
+        rewriteRun(
+          spec -> spec.recipe(new AddPropertyComment(
+            "management.metrics.enable.process.files",
+            "myComment",
+            false
+          )),
+          properties(
+            """
+              xxx=true
+              management.metrics.enable.process.files=true
+              yyy=true
+              """,
+            """
+              xxx=true
+              # myComment
+              management.metrics.enable.process.files=true
+              yyy=true
+              """
+          )
+        );
+    }
+
+    @Test
+    void shouldAcceptExistingComment() {
+        rewriteRun(
+          spec -> spec.recipe(new AddPropertyComment(
+            "management.metrics.enable.process.files",
+            "myComment",
+            false
+          )),
+          properties(
+            """
+              # myComment
+              management.metrics.enable.process.files=true
+              """
+          )
+        );
+    }
+
+    @Test
+    void shouldSkipNotExistingProperty() {
+        rewriteRun(
+          spec -> spec.recipe(new AddPropertyComment(
+            "xxx",
+            "myComment",
+            false
+          )),
+          properties(
+            """
+              yyy=true
+              """
+          )
+        );
+    }
+
+    @Test
+    void shouldCommentOutFirstProperty() {
+        rewriteRun(
+          spec -> spec.recipe(new AddPropertyComment(
+            "management.metrics.enable.process.files",
+            "myComment",
+            true
+          )),
+          properties(
+            """
+              management.metrics.enable.process.files=true
+              yyy=true
+              """,
+            """
+              # myComment
+              # management.metrics.enable.process.files=true
+              yyy=true
+              """
+          )
+        );
+    }
+
+    @Test
+    void shouldCommentOutMiddleProperty() {
+        rewriteRun(
+          spec -> spec.recipe(new AddPropertyComment(
+            "management.metrics.enable.process.files",
+            "myComment",
+            true
+          )),
+          properties(
+            """
+              xxx=true
+              management.metrics.enable.process.files=true
+              yyy=true
+              """,
+            """
+              xxx=true
+              # myComment
+              # management.metrics.enable.process.files=true
+              yyy=true
+              """
+          )
+        );
+    }
+
+    @Test
+    void shouldAcceptExistingCommentAndCommentOutProperty() {
+        rewriteRun(
+          spec -> spec.recipe(new AddPropertyComment(
+            "management.metrics.enable.process.files",
+            "myComment",
+            true
+          )),
+          properties(
+            """
+              # myComment
+              management.metrics.enable.process.files=true
+              """,
+            """
+              # myComment
+              # management.metrics.enable.process.files=true
+              """
+          )
+        );
+    }
+
+    @Test
+    void shouldASkipCommentOutProperty() {
+        rewriteRun(
+          spec -> spec.recipe(new AddPropertyComment(
+            "management.metrics.enable.process.files",
+            "myComment",
+            true
+          )),
+          properties(
+            """
+              # myComment
+              # management.metrics.enable.process.files=true
+              """
+          )
+        );
+    }
+}