diff --git a/x-pack/plugins/fleet/server/services/agents/actions.ts b/x-pack/plugins/fleet/server/services/agents/actions.ts
index c4f3530892543a..acd9ecb8b11d37 100644
--- a/x-pack/plugins/fleet/server/services/agents/actions.ts
+++ b/x-pack/plugins/fleet/server/services/agents/actions.ts
@@ -123,16 +123,6 @@ export async function cancelAgentAction(esClient: ElasticsearchClient, actionId:
     if (!hit._source || !hit._source.agents || !hit._source.action_id) {
       continue;
     }
-    await createAgentAction(esClient, {
-      id: cancelActionId,
-      type: 'CANCEL',
-      agents: hit._source.agents,
-      data: {
-        target_id: hit._source.action_id,
-      },
-      created_at: now,
-      expiration: hit._source.expiration,
-    });
     if (hit._source.type === 'UPGRADE') {
       await bulkUpdateAgents(
         esClient,
@@ -145,6 +135,16 @@ export async function cancelAgentAction(esClient: ElasticsearchClient, actionId:
         }))
       );
     }
+    await createAgentAction(esClient, {
+      id: cancelActionId,
+      type: 'CANCEL',
+      agents: hit._source.agents,
+      data: {
+        target_id: hit._source.action_id,
+      },
+      created_at: now,
+      expiration: hit._source.expiration,
+    });
   }
 
   return {
diff --git a/x-pack/plugins/fleet/server/services/agents/unenroll.ts b/x-pack/plugins/fleet/server/services/agents/unenroll.ts
index d8a5b4b32a101b..990ce903e08aa0 100644
--- a/x-pack/plugins/fleet/server/services/agents/unenroll.ts
+++ b/x-pack/plugins/fleet/server/services/agents/unenroll.ts
@@ -55,14 +55,14 @@ export async function unenrollAgent(
     return forceUnenrollAgent(soClient, esClient, agentId);
   }
   const now = new Date().toISOString();
+  await updateAgent(esClient, agentId, {
+    unenrollment_started_at: now,
+  });
   await createAgentAction(esClient, {
     agents: [agentId],
     created_at: now,
     type: 'UNENROLL',
   });
-  await updateAgent(esClient, agentId, {
-    unenrollment_started_at: now,
-  });
 }
 
 export async function unenrollAgents(
@@ -128,6 +128,17 @@ async function unenrollBatch(
       }, []);
 
   const now = new Date().toISOString();
+
+  // Update the necessary agents
+  const updateData = options.revoke
+    ? { unenrolled_at: now, active: false }
+    : { unenrollment_started_at: now };
+
+  await bulkUpdateAgents(
+    esClient,
+    agentsToUpdate.map(({ id }) => ({ agentId: id, data: updateData }))
+  );
+
   if (options.revoke) {
     // Get all API keys that need to be invalidated
     await invalidateAPIKeysForAgents(agentsToUpdate);
@@ -140,16 +151,6 @@ async function unenrollBatch(
     });
   }
 
-  // Update the necessary agents
-  const updateData = options.revoke
-    ? { unenrolled_at: now, active: false }
-    : { unenrollment_started_at: now };
-
-  await bulkUpdateAgents(
-    esClient,
-    agentsToUpdate.map(({ id }) => ({ agentId: id, data: updateData }))
-  );
-
   return {
     items: errorsToResults(givenAgents, outgoingErrors, undefined, skipSuccess),
   };
diff --git a/x-pack/plugins/fleet/server/services/agents/upgrade.ts b/x-pack/plugins/fleet/server/services/agents/upgrade.ts
index efe363b2b46b85..a2e46211efff29 100644
--- a/x-pack/plugins/fleet/server/services/agents/upgrade.ts
+++ b/x-pack/plugins/fleet/server/services/agents/upgrade.ts
@@ -58,6 +58,10 @@ export async function sendUpgradeAgentAction({
       `Cannot upgrade agent ${agentId} in hosted agent policy ${agentPolicy.id}`
     );
   }
+  await updateAgent(esClient, agentId, {
+    upgraded_at: null,
+    upgrade_started_at: now,
+  });
 
   await createAgentAction(esClient, {
     agents: [agentId],
@@ -66,10 +70,6 @@ export async function sendUpgradeAgentAction({
     ack_data: data,
     type: 'UPGRADE',
   });
-  await updateAgent(esClient, agentId, {
-    upgraded_at: null,
-    upgrade_started_at: now,
-  });
 }
 
 export async function sendUpgradeAgentsActions(
@@ -192,16 +192,6 @@ async function upgradeBatch(
     options.upgradeDurationSeconds
   );
 
-  await createAgentAction(esClient, {
-    id: options.actionId,
-    created_at: now,
-    data,
-    ack_data: data,
-    type: 'UPGRADE',
-    agents: agentsToUpdate.map((agent) => agent.id),
-    ...rollingUpgradeOptions,
-  });
-
   await bulkUpdateAgents(
     esClient,
     agentsToUpdate.map((agent) => ({
@@ -213,6 +203,16 @@ async function upgradeBatch(
     }))
   );
 
+  await createAgentAction(esClient, {
+    id: options.actionId,
+    created_at: now,
+    data,
+    ack_data: data,
+    type: 'UPGRADE',
+    agents: agentsToUpdate.map((agent) => agent.id),
+    ...rollingUpgradeOptions,
+  });
+
   return {
     items: errorsToResults(
       givenAgents,