diff --git a/src/main/java/org/openrewrite/java/spring/DeleteSpringProperty.java b/src/main/java/org/openrewrite/java/spring/DeleteSpringProperty.java
index 1b9cd9198..b54d42df7 100644
--- a/src/main/java/org/openrewrite/java/spring/DeleteSpringProperty.java
+++ b/src/main/java/org/openrewrite/java/spring/DeleteSpringProperty.java
@@ -42,6 +42,17 @@ public class DeleteSpringProperty extends Recipe {
 
     @Override
     public TreeVisitor<?, ExecutionContext> getVisitor() {
+        org.openrewrite.yaml.DeleteProperty yamlDeleteProperty =
+                new org.openrewrite.yaml.DeleteProperty(propertyKey, false, true, null);
+        DeleteProperty propertiesDeleteProperty =
+                new DeleteProperty(propertyKey, true);
+
+        String descendantPropertyKey = containsGlob(propertyKey) ? null : propertyKey + ".*";
+        org.openrewrite.yaml.DeleteProperty yamlDeleteDescendants =
+                descendantPropertyKey == null ? null : new org.openrewrite.yaml.DeleteProperty(descendantPropertyKey, false, true, null);
+        DeleteProperty propertiesDeleteDescendants =
+                descendantPropertyKey == null ? null : new DeleteProperty(descendantPropertyKey, true);
+
         return Preconditions.check(new IsPossibleSpringConfigFile(), new TreeVisitor<Tree, ExecutionContext>() {
             @Override
             public boolean isAcceptable(SourceFile sourceFile, ExecutionContext ctx) {
@@ -51,14 +62,24 @@ public boolean isAcceptable(SourceFile sourceFile, ExecutionContext ctx) {
             @Override
             public @Nullable Tree visit(@Nullable Tree t, ExecutionContext ctx) {
                 if (t instanceof Yaml.Documents) {
-                    t = new org.openrewrite.yaml.DeleteProperty(propertyKey, false, true, null)
-                            .getVisitor().visitNonNull(t, ctx);
+                    Tree deleted = yamlDeleteProperty.getVisitor().visitNonNull(t, ctx);
+                    if (yamlDeleteDescendants != null) {
+                        deleted = yamlDeleteDescendants.getVisitor().visitNonNull(deleted, ctx);
+                    }
+                    t = deleted;
                 } else if (t instanceof Properties.File) {
-                    t = new DeleteProperty(propertyKey, true)
-                            .getVisitor().visitNonNull(t, ctx);
+                    Tree deleted = propertiesDeleteProperty.getVisitor().visitNonNull(t, ctx);
+                    if (propertiesDeleteDescendants != null) {
+                        deleted = propertiesDeleteDescendants.getVisitor().visitNonNull(deleted, ctx);
+                    }
+                    t = deleted;
                 }
                 return t;
             }
         });
     }
+
+    private static boolean containsGlob(String propertyKey) {
+        return propertyKey.indexOf('*') >= 0 || propertyKey.indexOf('?') >= 0 || propertyKey.indexOf('[') >= 0;
+    }
 }
diff --git a/src/test/java/org/openrewrite/java/spring/DeleteSpringPropertyKeyTest.java b/src/test/java/org/openrewrite/java/spring/DeleteSpringPropertyKeyTest.java
index a611cbf02..0141b4ae1 100644
--- a/src/test/java/org/openrewrite/java/spring/DeleteSpringPropertyKeyTest.java
+++ b/src/test/java/org/openrewrite/java/spring/DeleteSpringPropertyKeyTest.java
@@ -134,6 +134,130 @@ void deleteLastKey() {
         );
     }
 
+    @Test
+    void deleteParentPropertyInProperties() {
+        rewriteRun(
+          spec -> spec.recipe(new DeleteSpringProperty("server.servlet.session.cookie")),
+          mavenProject("project",
+            srcMainResources(
+              properties(
+                """
+                  some=value
+                  server.servlet.session.cookie.name=fred
+                  server.servlet.session.cookie.path=/cookie-monster
+                  other=value
+                  """,
+                """
+                  some=value
+                  other=value
+                  """
+              )
+            )
+          )
+        );
+    }
+
+    @Test
+    void deleteParentPropertyInYaml() {
+        rewriteRun(
+          spec -> spec.recipe(new DeleteSpringProperty("server.servlet.session.cookie")),
+          mavenProject("project",
+            srcMainResources(
+              yaml(
+                """
+                  some: value
+                  server:
+                    servlet:
+                      session:
+                        cookie:
+                          name: fred
+                          path: /cookie-monster
+                  other: value
+                  """,
+                """
+                  some: value
+                  other: value
+                  """
+              )
+            )
+          )
+        );
+    }
+
+    @Test
+    void deleteParentPropertyInCoalescedYaml() {
+        rewriteRun(
+          spec -> spec.recipe(new DeleteSpringProperty("server.servlet.session.cookie")),
+          mavenProject("project",
+            srcMainResources(
+              yaml(
+                """
+                  some: value
+                  server.servlet.session.cookie.name: fred
+                  server.servlet.session.cookie.path: /cookie-monster
+                  other: value
+                  """,
+                """
+                  some: value
+                  other: value
+                  """
+              )
+            )
+          )
+        );
+    }
+
+    @Test
+    void deleteParentPropertyViaGlobAcrossFormats() {
+        rewriteRun(
+          spec -> spec.recipe(new DeleteSpringProperty("server.servlet.session.cookie.*")),
+          mavenProject("project",
+            srcMainResources(
+              properties(
+                """
+                  some=value
+                  server.servlet.session.cookie.name=fred
+                  server.servlet.session.cookie.path=/cookie-monster
+                  other=value
+                  """,
+                """
+                  some=value
+                  other=value
+                  """
+              ),
+              yaml(
+                """
+                  some: value
+                  server:
+                    servlet:
+                      session:
+                        cookie:
+                          name: fred
+                          path: /cookie-monster
+                  other: value
+                  """,
+                """
+                  some: value
+                  other: value
+                  """
+              ),
+              yaml(
+                """
+                  some: value
+                  server.servlet.session.cookie.name: fred
+                  server.servlet.session.cookie.path: /cookie-monster
+                  other: value
+                  """,
+                """
+                  some: value
+                  other: value
+                  """
+              )
+            )
+          )
+        );
+    }
+
     @Test
     void doesNotModifyNonSpringYamlFiles() {
         rewriteRun(