diff --git a/boms/geode-all-bom/src/test/resources/expected-pom.xml b/boms/geode-all-bom/src/test/resources/expected-pom.xml
index 5604883c767..bfb65e2d017 100644
--- a/boms/geode-all-bom/src/test/resources/expected-pom.xml
+++ b/boms/geode-all-bom/src/test/resources/expected-pom.xml
@@ -470,27 +470,27 @@
       <dependency>
         <groupId>com.fasterxml.jackson.core</groupId>
         <artifactId>jackson-annotations</artifactId>
-        <version>2.18.6</version>
+        <version>2.21</version>
       </dependency>
       <dependency>
         <groupId>com.fasterxml.jackson.core</groupId>
         <artifactId>jackson-core</artifactId>
-        <version>2.18.6</version>
+        <version>2.21.2</version>
       </dependency>
       <dependency>
         <groupId>com.fasterxml.jackson.core</groupId>
         <artifactId>jackson-databind</artifactId>
-        <version>2.18.6</version>
+        <version>2.21.2</version>
       </dependency>
       <dependency>
         <groupId>com.fasterxml.jackson.datatype</groupId>
         <artifactId>jackson-datatype-joda</artifactId>
-        <version>2.18.6</version>
+        <version>2.21.2</version>
       </dependency>
       <dependency>
         <groupId>com.fasterxml.jackson.datatype</groupId>
         <artifactId>jackson-datatype-jsr310</artifactId>
-        <version>2.18.6</version>
+        <version>2.21.2</version>
       </dependency>
       <dependency>
         <groupId>com.jayway.jsonpath</groupId>
diff --git a/build-tools/geode-dependency-management/src/main/groovy/org/apache/geode/gradle/plugins/DependencyConstraints.groovy b/build-tools/geode-dependency-management/src/main/groovy/org/apache/geode/gradle/plugins/DependencyConstraints.groovy
index b72d06e3b59..e16a6fedd6d 100644
--- a/build-tools/geode-dependency-management/src/main/groovy/org/apache/geode/gradle/plugins/DependencyConstraints.groovy
+++ b/build-tools/geode-dependency-management/src/main/groovy/org/apache/geode/gradle/plugins/DependencyConstraints.groovy
@@ -53,8 +53,9 @@ class DependencyConstraints {
     deps.put("slf4j-api.version", "2.0.17")
     deps.put("jakarta.transaction-api.version", "2.0.1")
     deps.put("jboss-modules.version", "1.11.0.Final")
-    deps.put("jackson.version", "2.18.6")
-    deps.put("jackson.databind.version", "2.18.6")
+    deps.put("jackson.version", "2.21.2")
+    deps.put("jackson.annotations.version", "2.21")
+    deps.put("jackson.databind.version", "2.21.2")
     // Spring Framework 6.x Migration
     deps.put("springshell.version", "3.3.3")
     deps.put("springframework.version", "6.1.21")
@@ -218,8 +219,11 @@ class DependencyConstraints {
       entry('mockito-junit-jupiter')
     }
 
-    dependencySet(group: 'com.fasterxml.jackson.core', version: get('jackson.version')) {
+    dependencySet(group: 'com.fasterxml.jackson.core', version: get('jackson.annotations.version')) {
       entry('jackson-annotations')
+    }
+
+    dependencySet(group: 'com.fasterxml.jackson.core', version: get('jackson.version')) {
       entry('jackson-core')
     }
 
diff --git a/geode-assembly/src/integrationTest/resources/assembly_content.txt b/geode-assembly/src/integrationTest/resources/assembly_content.txt
index 6489852bb96..bf18c802121 100644
--- a/geode-assembly/src/integrationTest/resources/assembly_content.txt
+++ b/geode-assembly/src/integrationTest/resources/assembly_content.txt
@@ -964,12 +964,12 @@ lib/httpclient5-5.4.4.jar
 lib/httpcore5-5.3.4.jar
 lib/httpcore5-h2-5.3.4.jar
 lib/istack-commons-runtime-4.1.1.jar
-lib/jackson-annotations-2.18.6.jar
-lib/jackson-core-2.18.6.jar
-lib/jackson-databind-2.18.6.jar
-lib/jackson-dataformat-yaml-2.18.6.jar
-lib/jackson-datatype-joda-2.18.6.jar
-lib/jackson-datatype-jsr310-2.18.6.jar
+lib/jackson-annotations-2.21.jar
+lib/jackson-core-2.21.2.jar
+lib/jackson-databind-2.21.2.jar
+lib/jackson-dataformat-yaml-2.21.2.jar
+lib/jackson-datatype-joda-2.21.2.jar
+lib/jackson-datatype-jsr310-2.21.2.jar
 lib/jakarta.activation-api-2.1.3.jar
 lib/jakarta.annotation-api-2.1.1.jar
 lib/jakarta.el-api-5.0.0.jar
diff --git a/geode-assembly/src/integrationTest/resources/gfsh_dependency_classpath.txt b/geode-assembly/src/integrationTest/resources/gfsh_dependency_classpath.txt
index 98275ee76de..e5fa80c5641 100644
--- a/geode-assembly/src/integrationTest/resources/gfsh_dependency_classpath.txt
+++ b/geode-assembly/src/integrationTest/resources/gfsh_dependency_classpath.txt
@@ -21,12 +21,12 @@ spring-shell-starter-3.3.3.jar
 spring-web-6.1.21.jar
 commons-lang3-3.18.0.jar
 rmiio-2.1.2.jar
-jackson-datatype-joda-2.18.6.jar
-jackson-annotations-2.18.6.jar
-jackson-dataformat-yaml-2.18.6.jar
-jackson-core-2.18.6.jar
-jackson-datatype-jsr310-2.18.6.jar
-jackson-databind-2.18.6.jar
+jackson-datatype-joda-2.21.2.jar
+jackson-annotations-2.21.jar
+jackson-dataformat-yaml-2.21.2.jar
+jackson-core-2.21.2.jar
+jackson-datatype-jsr310-2.21.2.jar
+jackson-databind-2.21.2.jar
 swagger-annotations-2.2.22.jar
 jaxb-runtime-4.0.2.jar
 jaxb-core-4.0.2.jar
diff --git a/geode-server-all/src/integrationTest/resources/dependency_classpath.txt b/geode-server-all/src/integrationTest/resources/dependency_classpath.txt
index 6f428eb90b7..661341dbb35 100644
--- a/geode-server-all/src/integrationTest/resources/dependency_classpath.txt
+++ b/geode-server-all/src/integrationTest/resources/dependency_classpath.txt
@@ -19,12 +19,12 @@ geode-unsafe-0.0.0.jar
 geode-deployment-legacy-0.0.0.jar
 snappy-0.5.jar
 swagger-annotations-2.2.22.jar
-jackson-datatype-jsr310-2.18.6.jar
-jackson-annotations-2.18.6.jar
-jackson-dataformat-yaml-2.18.6.jar
-jackson-core-2.18.6.jar
-jackson-datatype-joda-2.18.6.jar
-jackson-databind-2.18.6.jar
+jackson-datatype-jsr310-2.21.2.jar
+jackson-annotations-2.21.jar
+jackson-dataformat-yaml-2.21.2.jar
+jackson-core-2.21.2.jar
+jackson-datatype-joda-2.21.2.jar
+jackson-databind-2.21.2.jar
 httpclient5-5.4.4.jar
 httpcore5-h2-5.3.4.jar
 httpcore5-5.3.4.jar