diff --git a/util/csaupgrade/upgrade_test.go b/util/csaupgrade/upgrade_test.go
index 8f9a2e74..26bd0318 100644
--- a/util/csaupgrade/upgrade_test.go
+++ b/util/csaupgrade/upgrade_test.go
@@ -13,12 +13,17 @@ import (
 func TestUpgradeCSA(t *testing.T) {
 
 	cases := []struct {
+		Name           string
 		CSAManager     string
 		SSAManager     string
 		OriginalObject []byte
 		ExpectedObject []byte
 	}{
 		{
+			// Case where there is a CSA entry with the given name, but no SSA entry
+			// is found. Expect that the CSA entry is converted to an SSA entry
+			// and renamed.
+			Name:       "csa-basic-direct-conversion",
 			CSAManager: "kubectl-client-side-apply",
 			SSAManager: "kubectl",
 			OriginalObject: []byte(`
@@ -74,35 +79,406 @@ metadata:
     time: "2022-08-22T23:08:23Z"
   name: test
   namespace: default  
+`),
+		},
+		{
+			// This is the case when kubectl --server-side is used for the first time
+			// Server creates duplicate managed fields entry - one for Update and another
+			// for Apply. Expect entries to be merged into one entry, which is unchanged
+			// from initial SSA.
+			Name:       "csa-combine-with-ssa-duplicate-keys",
+			CSAManager: "kubectl-client-side-apply",
+			SSAManager: "kubectl",
+			OriginalObject: []byte(`
+apiVersion: v1
+data: {}
+kind: ConfigMap
+metadata:
+  annotations:
+    kubectl.kubernetes.io/last-applied-configuration: |
+      {"apiVersion":"v1","data":{"key":"value","legacy":"unused"},"kind":"ConfigMap","metadata":{"annotations":{},"name":"test","namespace":"default"}}
+  creationTimestamp: "2022-08-22T23:08:23Z"
+  managedFields:
+  - apiVersion: v1
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+        f:legacy: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl
+    operation: Apply
+    time: "2022-08-23T23:08:23Z"
+  - apiVersion: v1
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+        f:legacy: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  name: test
+  namespace: default
+`),
+			ExpectedObject: []byte(`
+apiVersion: v1
+data: {}
+kind: ConfigMap
+metadata:
+  annotations:
+    kubectl.kubernetes.io/last-applied-configuration: |
+      {"apiVersion":"v1","data":{"key":"value","legacy":"unused"},"kind":"ConfigMap","metadata":{"annotations":{},"name":"test","namespace":"default"}}
+  creationTimestamp: "2022-08-22T23:08:23Z"
+  managedFields:
+  - apiVersion: v1
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+        f:legacy: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl
+    operation: Apply
+    time: "2022-08-23T23:08:23Z"
+  name: test
+  namespace: default  
+`),
+		},
+		{
+			// This is the case when kubectl --server-side is used for the first time,
+			// but then a key is removed. A bug would take place where key is left in
+			// CSA entry but no longer present in SSA entry, so it would not be pruned.
+			// This shows that upgrading such an object results in correct behavior next
+			// time SSA applier
+			// Expect final object to have all keys from both entries
+			Name:       "csa-combine-with-ssa-additional-keys",
+			CSAManager: "kubectl-client-side-apply",
+			SSAManager: "kubectl",
+			OriginalObject: []byte(`
+apiVersion: v1
+data: {}
+kind: ConfigMap
+metadata:
+  annotations:
+    kubectl.kubernetes.io/last-applied-configuration: |
+      {"apiVersion":"v1","data":{"key":"value","legacy":"unused"},"kind":"ConfigMap","metadata":{"annotations":{},"name":"test","namespace":"default"}}
+  creationTimestamp: "2022-08-22T23:08:23Z"
+  managedFields:
+  - apiVersion: v1
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl
+    operation: Apply
+    time: "2022-08-23T23:08:23Z"
+  - apiVersion: v1
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+        f:legacy: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  name: test
+  namespace: default
+`),
+			ExpectedObject: []byte(`
+apiVersion: v1
+data: {}
+kind: ConfigMap
+metadata:
+  annotations:
+    kubectl.kubernetes.io/last-applied-configuration: |
+      {"apiVersion":"v1","data":{"key":"value","legacy":"unused"},"kind":"ConfigMap","metadata":{"annotations":{},"name":"test","namespace":"default"}}
+  creationTimestamp: "2022-08-22T23:08:23Z"
+  managedFields:
+  - apiVersion: v1
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+        f:legacy: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl
+    operation: Apply
+    time: "2022-08-23T23:08:23Z"
+  name: test
+  namespace: default  
+`),
+		},
+		{
+			// Case when there are multiple CSA versions on the object which do not
+			// match the version from the apply entry. Shows they are tossed away
+			// without being merged.
+			Name:       "csa-no-applicable-version",
+			CSAManager: "kubectl-client-side-apply",
+			SSAManager: "kubectl",
+			OriginalObject: []byte(`
+apiVersion: v1
+data: {}
+kind: ConfigMap
+metadata:
+  annotations:
+    kubectl.kubernetes.io/last-applied-configuration: |
+      {"apiVersion":"v1","data":{"key":"value","legacy":"unused"},"kind":"ConfigMap","metadata":{"annotations":{},"name":"test","namespace":"default"}}
+  creationTimestamp: "2022-08-22T23:08:23Z"
+  managedFields:
+  - apiVersion: v5
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+        f:legacy: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl
+    operation: Apply
+    time: "2022-08-23T23:08:23Z"
+  - apiVersion: v1
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        f:key2: {}
+      f:metadata:
+        f:annotations:
+          f:hello2: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  - apiVersion: v2
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        f:key3: {}
+      f:metadata:
+        f:annotations:
+          f:hello3: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  - apiVersion: v3
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        f:key4: {}
+      f:metadata:
+        f:annotations:
+          f:hello3: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  - apiVersion: v4
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        f:key5: {}
+      f:metadata:
+        f:annotations:
+          f:hello4: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  name: test
+  namespace: default
+`),
+			ExpectedObject: []byte(`
+apiVersion: v1
+data: {}
+kind: ConfigMap
+metadata:
+  annotations:
+    kubectl.kubernetes.io/last-applied-configuration: |
+      {"apiVersion":"v1","data":{"key":"value","legacy":"unused"},"kind":"ConfigMap","metadata":{"annotations":{},"name":"test","namespace":"default"}}
+  creationTimestamp: "2022-08-22T23:08:23Z"
+  managedFields:
+  - apiVersion: v5
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+        f:legacy: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl
+    operation: Apply
+    time: "2022-08-23T23:08:23Z"
+  name: test
+  namespace: default  
+`),
+		},
+		{
+			// Case when there are multiple CSA versions on the object which do not
+			// match the version from the apply entry, and one which does.
+			// Shows that CSA entry with matching version is unioned into the SSA entry.
+			Name:       "csa-single-applicable-version",
+			CSAManager: "kubectl-client-side-apply",
+			SSAManager: "kubectl",
+			OriginalObject: []byte(`
+apiVersion: v1
+data: {}
+kind: ConfigMap
+metadata:
+  annotations:
+    kubectl.kubernetes.io/last-applied-configuration: |
+      {"apiVersion":"v1","data":{"key":"value","legacy":"unused"},"kind":"ConfigMap","metadata":{"annotations":{},"name":"test","namespace":"default"}}
+  creationTimestamp: "2022-08-22T23:08:23Z"
+  managedFields:
+  - apiVersion: v5
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+        f:legacy: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl
+    operation: Apply
+    time: "2022-08-23T23:08:23Z"
+  - apiVersion: v5
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        f:key2: {}
+      f:metadata:
+        f:annotations:
+          f:hello2: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  - apiVersion: v2
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        f:key3: {}
+      f:metadata:
+        f:annotations:
+          f:hello3: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  - apiVersion: v3
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        f:key4: {}
+      f:metadata:
+        f:annotations:
+          f:hello4: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  - apiVersion: v4
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        f:key5: {}
+      f:metadata:
+        f:annotations:
+          f:hello5: {}
+    manager: kubectl-client-side-apply
+    operation: Update
+    time: "2022-08-22T23:08:23Z"
+  name: test
+  namespace: default
+`),
+			ExpectedObject: []byte(`
+apiVersion: v1
+data: {}
+kind: ConfigMap
+metadata:
+  annotations:
+    kubectl.kubernetes.io/last-applied-configuration: |
+      {"apiVersion":"v1","data":{"key":"value","legacy":"unused"},"kind":"ConfigMap","metadata":{"annotations":{},"name":"test","namespace":"default"}}
+  creationTimestamp: "2022-08-22T23:08:23Z"
+  managedFields:
+  - apiVersion: v5
+    fieldsType: FieldsV1
+    fieldsV1:
+      f:data:
+        .: {}
+        f:key: {}
+        f:key2: {}
+        f:legacy: {}
+      f:metadata:
+        f:annotations:
+          .: {}
+          f:hello2: {}
+          f:kubectl.kubernetes.io/last-applied-configuration: {}
+    manager: kubectl
+    operation: Apply
+    time: "2022-08-23T23:08:23Z"
+  name: test
+  namespace: default  
 `),
 		},
 	}
 
 	for _, testCase := range cases {
-		initialObject := unstructured.Unstructured{}
-		err := yaml.Unmarshal(testCase.OriginalObject, &initialObject)
-		if err != nil {
-			t.Fatal(err)
-		}
+		t.Run(testCase.Name, func(t *testing.T) {
+			initialObject := unstructured.Unstructured{}
+			err := yaml.Unmarshal(testCase.OriginalObject, &initialObject)
+			if err != nil {
+				t.Fatal(err)
+			}
 
-		upgraded, err := csaupgrade.UpgradeManagedFields(
-			&initialObject,
-			testCase.CSAManager,
-			testCase.SSAManager,
-		)
+			upgraded, err := csaupgrade.UpgradeManagedFields(
+				&initialObject,
+				testCase.CSAManager,
+				testCase.SSAManager,
+			)
 
-		if err != nil {
-			t.Fatal(err)
-		}
+			if err != nil {
+				t.Fatal(err)
+			}
 
-		expectedObject := unstructured.Unstructured{}
-		err = yaml.Unmarshal(testCase.ExpectedObject, &expectedObject)
-		if err != nil {
-			t.Fatal(err)
-		}
+			expectedObject := unstructured.Unstructured{}
+			err = yaml.Unmarshal(testCase.ExpectedObject, &expectedObject)
+			if err != nil {
+				t.Fatal(err)
+			}
 
-		if !reflect.DeepEqual(&expectedObject, upgraded) {
-			t.Fatal(cmp.Diff(&expectedObject, upgraded))
-		}
+			if !reflect.DeepEqual(&expectedObject, upgraded) {
+				t.Fatal(cmp.Diff(&expectedObject, upgraded))
+			}
+		})
 	}
 }