diff --git a/charts/cluster/test/database-management/01-database-parameters-assert.yaml b/charts/cluster/test/database-management/01-database-parameters-assert.yaml
index e300a8bdce..b5987248af 100644
--- a/charts/cluster/test/database-management/01-database-parameters-assert.yaml
+++ b/charts/cluster/test/database-management/01-database-parameters-assert.yaml
@@ -42,7 +42,7 @@ spec:
   extensions:
     - name: pg_search
       ensure: absent
-      version: "0.15.21"
+      version: "0.19.11"
       schema: test-schema
 
 ---
@@ -75,5 +75,5 @@ spec:
   extensions:
     - name: pg_search
       ensure: absent
-      version: "0.15.21"
+      version: "0.19.11"
       schema: test-schema
diff --git a/charts/cluster/test/database-management/01-database-parameters.yaml b/charts/cluster/test/database-management/01-database-parameters.yaml
index 71de78b369..6b5e2730a0 100644
--- a/charts/cluster/test/database-management/01-database-parameters.yaml
+++ b/charts/cluster/test/database-management/01-database-parameters.yaml
@@ -1,6 +1,7 @@
 type: postgresql
 version:
   postgresql: "17"
+  paradedb: "0.19.11"
 
 cluster:
   instances: 1
@@ -33,7 +34,7 @@ databases:
     extensions:
       - name: pg_search
         ensure: absent
-        version: "0.15.21"
+        version: "0.19.11"
         schema: test-schema
 
   - name: test-db-builtin
@@ -58,5 +59,5 @@ databases:
     extensions:
       - name: pg_search
         ensure: absent
-        version: "0.15.21"
+        version: "0.19.11"
         schema: test-schema
diff --git a/charts/cluster/test/database-management/02-extension-upgrade-init-assert.yaml b/charts/cluster/test/database-management/02-extension-upgrade-init-assert.yaml
new file mode 100644
index 0000000000..8042b3c641
--- /dev/null
+++ b/charts/cluster/test/database-management/02-extension-upgrade-init-assert.yaml
@@ -0,0 +1,25 @@
+apiVersion: postgresql.cnpg.io/v1
+kind: Cluster
+metadata:
+  name: extension-upgrade-cluster
+status:
+  readyInstances: 2
+  phase: Cluster in healthy state
+---
+apiVersion: postgresql.cnpg.io/v1
+kind: Database
+metadata:
+  name: extension-upgrade-cluster-cluster
+spec:
+  name: test-db-icu
+  cluster:
+    name: extension-upgrade-cluster
+  ensure: present
+  owner: test-owner
+  template: template1
+  encoding: UTF8
+  databaseReclaimPolicy: retain
+  extensions:
+    - name: pg_search
+      ensure: present
+      version: "0.19.10"
diff --git a/charts/cluster/test/database-management/02-extension-upgrade-init.yaml b/charts/cluster/test/database-management/02-extension-upgrade-init.yaml
new file mode 100644
index 0000000000..1304e5c3d3
--- /dev/null
+++ b/charts/cluster/test/database-management/02-extension-upgrade-init.yaml
@@ -0,0 +1,16 @@
+type: postgresql
+version:
+  postgresql: "17"
+  paradedb: "0.19.10"
+
+cluster:
+  instances: 2
+
+databases:
+  - name: test-db-icu
+    ensure: present
+    owner: test-owner
+    encoding: UTF8
+    extensions:
+      - name: pg_search
+        ensure: present
diff --git a/charts/cluster/test/database-management/03-paradedb_extension_check-assert.yaml b/charts/cluster/test/database-management/03-paradedb_extension_check-assert.yaml
new file mode 100644
index 0000000000..f52779599c
--- /dev/null
+++ b/charts/cluster/test/database-management/03-paradedb_extension_check-assert.yaml
@@ -0,0 +1,6 @@
+apiVersion: batch/v1
+kind: Job
+metadata:
+  name: test-db-icu-version-check-before
+status:
+  succeeded: 1
diff --git a/charts/cluster/test/database-management/03-paradedb_extension_check.yaml b/charts/cluster/test/database-management/03-paradedb_extension_check.yaml
new file mode 100644
index 0000000000..4dec1d32fc
--- /dev/null
+++ b/charts/cluster/test/database-management/03-paradedb_extension_check.yaml
@@ -0,0 +1,32 @@
+apiVersion: batch/v1
+kind: Job
+metadata:
+  name: test-db-icu-version-check-before
+spec:
+  template:
+    spec:
+      restartPolicy: OnFailure
+      containers:
+      - name: data-test
+        env:
+          - name: DB_URI
+            valueFrom:
+              secretKeyRef:
+                name: extension-upgrade-cluster-app
+                key: uri
+        image: alpine:3.19
+        command: ['sh', '-c']
+        args:
+          - |
+            apk --no-cache add postgresql-client
+            PG_SEARCH_VERSION=$(psql "$DB_URI" -t) <<-EOSQL
+              SELECT version FROM paradedb.version_info();
+            EOSQL
+            echo $PG_SEARCH_VERSION
+            test "$PG_SEARCH_VERSION" = " 0.19.10"
+
+            EXTVERSION=$(psql "$DB_URI" -t) <<-EOSQL
+              SELECT extversion FROM pg_extension WHERE extname = 'pg_search';
+            EOSQL
+            echo $EXTVERSION
+            test "$EXTVERSION" = " 0.19.10"
diff --git a/charts/cluster/test/database-management/04-extension-upgrade-post-assert.yaml b/charts/cluster/test/database-management/04-extension-upgrade-post-assert.yaml
new file mode 100644
index 0000000000..25d84b7c01
--- /dev/null
+++ b/charts/cluster/test/database-management/04-extension-upgrade-post-assert.yaml
@@ -0,0 +1,25 @@
+apiVersion: postgresql.cnpg.io/v1
+kind: Cluster
+metadata:
+  name: extension-upgrade-cluster
+status:
+  readyInstances: 2
+  phase: Cluster in healthy state
+---
+apiVersion: postgresql.cnpg.io/v1
+kind: Database
+metadata:
+  name: extension-upgrade-cluster-cluster
+spec:
+  name: test-db-icu
+  cluster:
+    name: extension-upgrade-cluster
+  ensure: present
+  owner: test-owner
+  template: template1
+  encoding: UTF8
+  databaseReclaimPolicy: retain
+  extensions:
+    - name: pg_search
+      ensure: present
+      version: "0.19.11"
diff --git a/charts/cluster/test/database-management/04-extension-upgrade-post.yaml b/charts/cluster/test/database-management/04-extension-upgrade-post.yaml
new file mode 100644
index 0000000000..8516037b16
--- /dev/null
+++ b/charts/cluster/test/database-management/04-extension-upgrade-post.yaml
@@ -0,0 +1,16 @@
+type: postgresql
+version:
+  postgresql: "17"
+  paradedb: "0.19.11"
+
+cluster:
+  instances: 2
+
+databases:
+  - name: test-db-icu
+    ensure: present
+    owner: test-owner
+    encoding: UTF8
+    extensions:
+      - name: pg_search
+        ensure: present
diff --git a/charts/cluster/test/database-management/05-paradedb_extension_check-assert.yaml b/charts/cluster/test/database-management/05-paradedb_extension_check-assert.yaml
new file mode 100644
index 0000000000..b75df162f3
--- /dev/null
+++ b/charts/cluster/test/database-management/05-paradedb_extension_check-assert.yaml
@@ -0,0 +1,6 @@
+apiVersion: batch/v1
+kind: Job
+metadata:
+  name: test-db-icu-version-check-after
+status:
+  succeeded: 1
diff --git a/charts/cluster/test/database-management/05-paradedb_extension_check.yaml b/charts/cluster/test/database-management/05-paradedb_extension_check.yaml
new file mode 100644
index 0000000000..62e8095d09
--- /dev/null
+++ b/charts/cluster/test/database-management/05-paradedb_extension_check.yaml
@@ -0,0 +1,32 @@
+apiVersion: batch/v1
+kind: Job
+metadata:
+  name: test-db-icu-version-check-after
+spec:
+  template:
+    spec:
+      restartPolicy: OnFailure
+      containers:
+      - name: data-test
+        env:
+          - name: DB_URI
+            valueFrom:
+              secretKeyRef:
+                name: extension-upgrade-cluster-app
+                key: uri
+        image: alpine:3.19
+        command: ['sh', '-c']
+        args:
+          - |
+            apk --no-cache add postgresql-client
+            PG_SEARCH_VERSION=$(psql "$DB_URI" -t) <<-EOSQL
+              SELECT version FROM paradedb.version_info();
+            EOSQL
+            echo $PG_SEARCH_VERSION
+            test "$PG_SEARCH_VERSION" = " 0.19.11"
+
+            EXTVERSION=$(psql "$DB_URI" -t) <<-EOSQL
+              SELECT extversion FROM pg_extension WHERE extname = 'pg_search';
+            EOSQL
+            echo $EXTVERSION
+            test "$EXTVERSION" = " 0.19.11"
diff --git a/charts/cluster/test/database-management/chainsaw-test.yaml b/charts/cluster/test/database-management/chainsaw-test.yaml
index fde0372a3e..c0426d45fc 100644
--- a/charts/cluster/test/database-management/chainsaw-test.yaml
+++ b/charts/cluster/test/database-management/chainsaw-test.yaml
@@ -24,8 +24,65 @@ spec:
                 database-parameters ../../
         - assert:
             file: ./01-database-parameters-assert.yaml
+
+    - name: Provision a cluster with a database with the ParadeDB extension
+      try:
+        - script:
+            content: |
+              helm upgrade \
+                --install \
+                --namespace $NAMESPACE \
+                --values ./02-extension-upgrade-init.yaml \
+                --wait \
+                extension-upgrade ../../
+        - assert:
+            file: ./02-extension-upgrade-init-assert.yaml
+      catch:
+        - describe:
+            apiVersion: postgresql.cnpg.io/v1
+            kind: Cluster
+            name: extension-upgrade-paradedb
+        - podLogs:
+            selector: cnpg.io/cluster=extension-upgrade-paradedb
+        - script:
+            content: |
+              echo "=== Cluster Status ==="
+              kubectl get cluster extension-upgrade-paradedb -n $NAMESPACE -o yaml | grep -A 50 "status:"
+              echo "=== Pod Status ==="
+              kubectl get pods -n $NAMESPACE -l cnpg.io/cluster=extension-upgrade-paradedb -o wide
+              echo "=== Pod Events ==="
+              kubectl get events -n $NAMESPACE --sort-by='.lastTimestamp' | tail -30
+
+    - name: Verify the ParadeDB extension version before upgrade
+      try:
+        - apply:
+            file: ./03-paradedb_extension_check.yaml
+        - assert:
+            file: ./03-paradedb_extension_check-assert.yaml
+
+    - name: Upgrade the ParadeDB cluster and the extension
+      try:
+        - script:
+            content: |
+              helm upgrade \
+                --install \
+                --namespace $NAMESPACE \
+                --values ./04-extension-upgrade-post.yaml \
+                --wait \
+                extension-upgrade ../../
+        - assert:
+            file: ./04-extension-upgrade-post-assert.yaml
+
+    - name: Verify the ParadeDB extension version after upgrade
+      try:
+        - apply:
+            file: ./05-paradedb_extension_check.yaml
+        - assert:
+            file: ./05-paradedb_extension_check-assert.yaml
+
     - name: cleanup
       try:
         - script:
             content: |
               helm uninstall --namespace $NAMESPACE database-parameters
+              helm uninstall --namespace $NAMESPACE extension-upgrade 
diff --git a/charts/cluster/values.yaml b/charts/cluster/values.yaml
index 964ef2934e..95ff3292ff 100644
--- a/charts/cluster/values.yaml
+++ b/charts/cluster/values.yaml
@@ -577,7 +577,7 @@ databases: []
  #   extensions: []                 # -- List of extensions to be created in the database.
  #    # - name: pg_search
  #    #   ensure: present           # -- Ensure the PostgreSQL extension is present or absent - defaults to "present".
- #    #   version: "0.15.21"        # -- Version of the extension to be installed, if not specified the latest version will be used.
+ #    #   version: "0.19.11"        # -- Version of the extension to be installed, if not specified the latest version will be used.
  #    #   schema: ""                # -- Schema where the extension will be installed, if not specified the extensions or current default object creation schema will be used.
  #   isTemplate: false              # -- Maps to the IS_TEMPLATE parameter. If true, the database is considered a template for new databases.
  #   locale: ""                     # -- Maps to the LC_COLLATE and LC_CTYPE parameters
diff --git a/charts/paradedb/test/database-management/chainsaw-test.yaml b/charts/paradedb/test/database-management/chainsaw-test.yaml
new file mode 100644
index 0000000000..d194d289b3
--- /dev/null
+++ b/charts/paradedb/test/database-management/chainsaw-test.yaml
@@ -0,0 +1,88 @@
+apiVersion: chainsaw.kyverno.io/v1alpha1
+kind: Test
+metadata:
+  name: database-management
+spec:
+  timeouts:
+    apply: 1s
+    assert: 300s
+    cleanup: 60s
+  steps:
+    - name: database-parameters
+      timeouts:
+        apply: 1s
+        assert: 5s
+        cleanup: 30s
+      try:
+        - script:
+            content: |
+              helm upgrade \
+                --install \
+                --namespace $NAMESPACE \
+                --values ./01-database-parameters.yaml \
+                --wait \
+                database-parameters ../../
+        - assert:
+            file: ./01-database-parameters-assert.yaml
+
+    - name: Provision a cluster with a database with the pg_search extension
+      try:
+        - script:
+            content: |
+              helm upgrade \
+                --install \
+                --namespace $NAMESPACE \
+                --values ./02-extension-upgrade-init.yaml \
+                --wait \
+                extension-upgrade ../../
+        - assert:
+            file: ./02-extension-upgrade-init-assert.yaml
+      catch:
+        - describe:
+            apiVersion: postgresql.cnpg.io/v1
+            kind: Cluster
+            name: extension-upgrade-cluster
+        - podLogs:
+            selector: cnpg.io/cluster=extension-upgrade-cluster
+        - script:
+            content: |
+              echo "=== Cluster Status ==="
+              kubectl get cluster extension-upgrade-cluster -n $NAMESPACE -o yaml | grep -A 50 "status:"
+              echo "=== Pod Status ==="
+              kubectl get pods -n $NAMESPACE -l cnpg.io/cluster=extension-upgrade-cluster -o wide
+              echo "=== Pod Events ==="
+              kubectl get events -n $NAMESPACE --sort-by='.lastTimestamp' | tail -30
+
+    - name: Verify the ParadeDB extension version before upgrade
+      try:
+        - apply:
+            file: ./03-cluster_extension_check.yaml
+        - assert:
+            file: ./03-cluster_extension_check-assert.yaml
+
+    - name: Upgrade the ParadeDB cluster and the extension
+      try:
+        - script:
+            content: |
+              helm upgrade \
+                --install \
+                --namespace $NAMESPACE \
+                --values ./04-extension-upgrade-post.yaml \
+                --wait \
+                extension-upgrade ../../
+        - assert:
+            file: ./04-extension-upgrade-post-assert.yaml
+
+    - name: Verify the ParadeDB extension version after upgrade
+      try:
+        - apply:
+            file: ./05-cluster_extension_check.yaml
+        - assert:
+            file: ./05-cluster_extension_check-assert.yaml
+
+    - name: cleanup
+      try:
+        - script:
+            content: |
+              helm uninstall --namespace $NAMESPACE database-parameters
+              helm uninstall --namespace $NAMESPACE extension-upgrade