diff --git a/x-pack/plugins/fleet/cypress/plugins/index.ts b/x-pack/plugins/fleet/cypress/plugins/index.ts
index d11dbb1e38ada..9fce88b6cd689 100644
--- a/x-pack/plugins/fleet/cypress/plugins/index.ts
+++ b/x-pack/plugins/fleet/cypress/plugins/index.ts
@@ -35,6 +35,7 @@ const plugin: Cypress.PluginConfig = (on, config) => {
         query,
         ignore_unavailable: ignoreUnavailable,
         refresh: true,
+        conflicts: 'proceed',
       });
     },
   });
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/tags_add_remove.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/tags_add_remove.tsx
index 70b4da44dad68..8307bc3467cc2 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/tags_add_remove.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/agent_list_page/components/tags_add_remove.tsx
@@ -123,12 +123,22 @@ export const TagsAddRemove: React.FC<Props> = ({
       // sending updated tags to add/remove, in case multiple actions are done quickly and the first one is not yet propagated
       const updatedTagsToAdd = tagsToAdd.concat(
         labels
-          .filter((tag) => tag.checked === 'on' && !selectedTags.includes(tag.label))
+          .filter(
+            (tag) =>
+              tag.checked === 'on' &&
+              !selectedTags.includes(tag.label) &&
+              !tagsToRemove.includes(tag.label)
+          )
           .map((tag) => tag.label)
       );
       const updatedTagsToRemove = tagsToRemove.concat(
         labels
-          .filter((tag) => tag.checked !== 'on' && selectedTags.includes(tag.label))
+          .filter(
+            (tag) =>
+              tag.checked !== 'on' &&
+              selectedTags.includes(tag.label) &&
+              !tagsToAdd.includes(tag.label)
+          )
           .map((tag) => tag.label)
       );
 
diff --git a/x-pack/plugins/fleet/server/services/agents/action_status.ts b/x-pack/plugins/fleet/server/services/agents/action_status.ts
index 8489c25e3fd8d..a057af185a066 100644
--- a/x-pack/plugins/fleet/server/services/agents/action_status.ts
+++ b/x-pack/plugins/fleet/server/services/agents/action_status.ts
@@ -64,7 +64,10 @@ export async function getActionStatuses(
     const matchingBucket = (acks?.aggregations?.ack_counts as any)?.buckets?.find(
       (bucket: any) => bucket.key === action.actionId
     );
-    const nbAgentsAck = (matchingBucket?.agent_count as any)?.value ?? 0;
+    const nbAgentsAck = Math.min(
+      matchingBucket?.doc_count ?? 0,
+      (matchingBucket?.agent_count as any)?.value ?? 0
+    );
     const completionTime = (matchingBucket?.max_timestamp as any)?.value_as_string;
     const nbAgentsActioned = action.nbAgentsActioned || action.nbAgentsActionCreated;
     const complete = nbAgentsAck >= nbAgentsActioned;
diff --git a/x-pack/plugins/fleet/server/services/agents/actions.test.ts b/x-pack/plugins/fleet/server/services/agents/actions.test.ts
index 97d7c73035e6d..7c88b4885b843 100644
--- a/x-pack/plugins/fleet/server/services/agents/actions.test.ts
+++ b/x-pack/plugins/fleet/server/services/agents/actions.test.ts
@@ -92,10 +92,14 @@ describe('Agent actions', () => {
       await cancelAgentAction(esClient, 'action1');
 
       expect(mockedBulkUpdateAgents).toBeCalled();
-      expect(mockedBulkUpdateAgents).toBeCalledWith(expect.anything(), [
-        expect.objectContaining({ agentId: 'agent1' }),
-        expect.objectContaining({ agentId: 'agent2' }),
-      ]);
+      expect(mockedBulkUpdateAgents).toBeCalledWith(
+        expect.anything(),
+        [
+          expect.objectContaining({ agentId: 'agent1' }),
+          expect.objectContaining({ agentId: 'agent2' }),
+        ],
+        {}
+      );
     });
   });
 });
diff --git a/x-pack/plugins/fleet/server/services/agents/actions.ts b/x-pack/plugins/fleet/server/services/agents/actions.ts
index 17c745bfd285f..8f9302bd31acd 100644
--- a/x-pack/plugins/fleet/server/services/agents/actions.ts
+++ b/x-pack/plugins/fleet/server/services/agents/actions.ts
@@ -8,6 +8,7 @@
 import uuid from 'uuid';
 import type { ElasticsearchClient } from '@kbn/core/server';
 
+import { appContextService } from '../app_context';
 import type {
   Agent,
   AgentAction,
@@ -101,6 +102,32 @@ export async function bulkCreateAgentActions(
   return actions;
 }
 
+export async function createErrorActionResults(
+  esClient: ElasticsearchClient,
+  actionId: string,
+  errors: Record<Agent['id'], Error>,
+  errorMessage: string
+) {
+  const errorCount = Object.keys(errors).length;
+  if (errorCount > 0) {
+    appContextService
+      .getLogger()
+      .info(
+        `Writing error action results of ${errorCount} agents. Possibly failed validation: ${errorMessage}.`
+      );
+
+    // writing out error result for those agents that have errors, so the action is not going to stay in progress forever
+    await bulkCreateAgentActionResults(
+      esClient,
+      Object.keys(errors).map((agentId) => ({
+        agentId,
+        actionId,
+        error: errors[agentId].message,
+      }))
+    );
+  }
+}
+
 export async function bulkCreateAgentActionResults(
   esClient: ElasticsearchClient,
   results: Array<{
@@ -227,16 +254,6 @@ 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,
@@ -246,9 +263,20 @@ export async function cancelAgentAction(esClient: ElasticsearchClient, actionId:
             upgraded_at: null,
             upgrade_started_at: null,
           },
-        }))
+        })),
+        {}
       );
     }
+    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/crud.ts b/x-pack/plugins/fleet/server/services/agents/crud.ts
index 55a244664238b..d62bbf4c414bb 100644
--- a/x-pack/plugins/fleet/server/services/agents/crud.ts
+++ b/x-pack/plugins/fleet/server/services/agents/crud.ts
@@ -11,7 +11,7 @@ import type { SavedObjectsClientContract, ElasticsearchClient } from '@kbn/core/
 import type { KueryNode } from '@kbn/es-query';
 import { fromKueryExpression, toElasticsearchQuery } from '@kbn/es-query';
 
-import type { AgentSOAttributes, Agent, BulkActionResult, ListWithKuery } from '../../types';
+import type { AgentSOAttributes, Agent, ListWithKuery } from '../../types';
 import { appContextService, agentPolicyService } from '..';
 import type { FleetServerAgent } from '../../../common/types';
 import { SO_SEARCH_LIMIT } from '../../../common/constants';
@@ -395,10 +395,11 @@ export async function bulkUpdateAgents(
   updateData: Array<{
     agentId: string;
     data: Partial<AgentSOAttributes>;
-  }>
-): Promise<{ items: BulkActionResult[] }> {
+  }>,
+  errors: { [key: string]: Error }
+): Promise<void> {
   if (updateData.length === 0) {
-    return { items: [] };
+    return;
   }
 
   const body = updateData.flatMap(({ agentId, data }) => [
@@ -419,14 +420,12 @@ export async function bulkUpdateAgents(
     refresh: 'wait_for',
   });
 
-  return {
-    items: res.items.map((item) => ({
-      id: item.update!._id as string,
-      success: !item.update!.error,
+  res.items
+    .filter((item) => item.update!.error)
+    .forEach((item) => {
       // @ts-expect-error it not assignable to ErrorCause
-      error: item.update!.error as Error,
-    })),
-  };
+      errors[item.update!._id as string] = item.update!.error as Error;
+    });
 }
 
 export async function deleteAgent(esClient: ElasticsearchClient, agentId: string) {
diff --git a/x-pack/plugins/fleet/server/services/agents/reassign_action_runner.ts b/x-pack/plugins/fleet/server/services/agents/reassign_action_runner.ts
index 96405e464b358..c15857bb4ae32 100644
--- a/x-pack/plugins/fleet/server/services/agents/reassign_action_runner.ts
+++ b/x-pack/plugins/fleet/server/services/agents/reassign_action_runner.ts
@@ -16,7 +16,7 @@ import { appContextService } from '../app_context';
 import { ActionRunner } from './action_runner';
 
 import { bulkUpdateAgents } from './crud';
-import { bulkCreateAgentActionResults, createAgentAction } from './actions';
+import { createErrorActionResults, createAgentAction } from './actions';
 import { getHostedPolicies, isHostedAgent } from './hosted_agent';
 import { BulkActionTaskType } from './bulk_actions_resolver';
 
@@ -72,7 +72,7 @@ export async function reassignBatch(
     throw new AgentReassignmentError('No agents to reassign, already assigned or hosted agents');
   }
 
-  const res = await bulkUpdateAgents(
+  await bulkUpdateAgents(
     esClient,
     agentsToUpdate.map((agent) => ({
       agentId: agent.id,
@@ -80,18 +80,12 @@ export async function reassignBatch(
         policy_id: options.newAgentPolicyId,
         policy_revision: null,
       },
-    }))
+    })),
+    errors
   );
 
-  res.items
-    .filter((item) => !item.success)
-    .forEach((item) => {
-      errors[item.id] = item.error!;
-    });
-
   const actionId = options.actionId ?? uuid();
-  const errorCount = Object.keys(errors).length;
-  const total = options.total ?? agentsToUpdate.length + errorCount;
+  const total = options.total ?? givenAgents.length;
 
   const now = new Date().toISOString();
   await createAgentAction(esClient, {
@@ -105,23 +99,12 @@ export async function reassignBatch(
     },
   });
 
-  if (errorCount > 0) {
-    appContextService
-      .getLogger()
-      .info(
-        `Skipping ${errorCount} agents, as failed validation (already assigned or assigned to hosted policy)`
-      );
-
-    // writing out error result for those agents that failed validation, so the action is not going to stay in progress forever
-    await bulkCreateAgentActionResults(
-      esClient,
-      Object.keys(errors).map((agentId) => ({
-        agentId,
-        actionId,
-        error: errors[agentId].message,
-      }))
-    );
-  }
+  await createErrorActionResults(
+    esClient,
+    actionId,
+    errors,
+    'already assigned or assigned to hosted policy'
+  );
 
   return { actionId };
 }
diff --git a/x-pack/plugins/fleet/server/services/agents/unenroll.test.ts b/x-pack/plugins/fleet/server/services/agents/unenroll.test.ts
index 79612b0bcbf06..5beb5c0a9ac00 100644
--- a/x-pack/plugins/fleet/server/services/agents/unenroll.test.ts
+++ b/x-pack/plugins/fleet/server/services/agents/unenroll.test.ts
@@ -115,7 +115,7 @@ describe('unenrollAgents (plural)', () => {
 
     // calls ES update with correct values
     const onlyRegular = [agentInRegularDoc._id, agentInRegularDoc2._id];
-    const calledWith = esClient.bulk.mock.calls[1][0];
+    const calledWith = esClient.bulk.mock.calls[0][0];
     const ids = (calledWith as estypes.BulkRequest)?.body
       ?.filter((i: any) => i.update !== undefined)
       .map((i: any) => i.update._id);
@@ -128,7 +128,7 @@ describe('unenrollAgents (plural)', () => {
     }
 
     // hosted policy is updated in action results with error
-    const calledWithActionResults = esClient.bulk.mock.calls[0][0] as estypes.BulkRequest;
+    const calledWithActionResults = esClient.bulk.mock.calls[1][0] as estypes.BulkRequest;
     // bulk write two line per create
     expect(calledWithActionResults.body?.length).toBe(2);
     const expectedObject = expect.objectContaining({
@@ -170,7 +170,7 @@ describe('unenrollAgents (plural)', () => {
     });
 
     expect(esClient.bulk.mock.calls.length).toEqual(3);
-    const bulkBody = (esClient.bulk.mock.calls[1][0] as estypes.BulkRequest)?.body?.[1] as any;
+    const bulkBody = (esClient.bulk.mock.calls[2][0] as estypes.BulkRequest)?.body?.[1] as any;
     expect(bulkBody.agent_id).toEqual(agentInRegularDoc._id);
     expect(bulkBody.action_id).toEqual('other-action');
   });
@@ -227,7 +227,7 @@ describe('unenrollAgents (plural)', () => {
 
     // calls ES update with correct values
     const onlyRegular = [agentInRegularDoc._id, agentInRegularDoc2._id];
-    const calledWith = esClient.bulk.mock.calls[2][0];
+    const calledWith = esClient.bulk.mock.calls[0][0];
     const ids = (calledWith as estypes.BulkRequest)?.body
       ?.filter((i: any) => i.update !== undefined)
       .map((i: any) => i.update._id);
@@ -239,13 +239,13 @@ describe('unenrollAgents (plural)', () => {
       expect(doc).toHaveProperty('unenrolled_at');
     }
 
-    const errorResults = esClient.bulk.mock.calls[1][0];
+    const errorResults = esClient.bulk.mock.calls[2][0];
     const errorIds = (errorResults as estypes.BulkRequest)?.body
       ?.filter((i: any) => i.agent_id)
       .map((i: any) => i.agent_id);
     expect(errorIds).toEqual([agentInHostedDoc._id]);
 
-    const actionResults = esClient.bulk.mock.calls[0][0];
+    const actionResults = esClient.bulk.mock.calls[1][0];
     const resultIds = (actionResults as estypes.BulkRequest)?.body
       ?.filter((i: any) => i.agent_id)
       .map((i: any) => i.agent_id);
@@ -290,7 +290,7 @@ describe('unenrollAgents (plural)', () => {
     expect(unenrolledResponse.actionId).toBeDefined();
 
     // calls ES update with correct values
-    const calledWith = esClient.bulk.mock.calls[1][0];
+    const calledWith = esClient.bulk.mock.calls[0][0];
     const ids = (calledWith as estypes.BulkRequest)?.body
       ?.filter((i: any) => i.update !== undefined)
       .map((i: any) => i.update._id);
@@ -302,7 +302,7 @@ describe('unenrollAgents (plural)', () => {
       expect(doc).toHaveProperty('unenrolled_at');
     }
 
-    const actionResults = esClient.bulk.mock.calls[0][0];
+    const actionResults = esClient.bulk.mock.calls[1][0];
     const resultIds = (actionResults as estypes.BulkRequest)?.body
       ?.filter((i: any) => i.agent_id)
       .map((i: any) => i.agent_id);
diff --git a/x-pack/plugins/fleet/server/services/agents/unenroll_action_runner.ts b/x-pack/plugins/fleet/server/services/agents/unenroll_action_runner.ts
index dd5b4e023c2a3..c735254f18256 100644
--- a/x-pack/plugins/fleet/server/services/agents/unenroll_action_runner.ts
+++ b/x-pack/plugins/fleet/server/services/agents/unenroll_action_runner.ts
@@ -25,6 +25,7 @@ import { bulkUpdateAgents } from './crud';
 import {
   bulkCreateAgentActionResults,
   createAgentAction,
+  createErrorActionResults,
   getUnenrollAgentActions,
 } from './actions';
 import { getHostedPolicies, isHostedAgent } from './hosted_agent';
@@ -81,13 +82,24 @@ export async function unenrollBatch(
         return agents;
       }, []);
 
+  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 })),
+    outgoingErrors
+  );
+
   const actionId = options.actionId ?? uuid();
-  const errorCount = Object.keys(outgoingErrors).length;
   const total = options.total ?? givenAgents.length;
 
   const agentIds = agentsToUpdate.map((agent) => agent.id);
 
-  const now = new Date().toISOString();
   if (options.revoke) {
     // Get all API keys that need to be invalidated
     await invalidateAPIKeysForAgents(agentsToUpdate);
@@ -104,32 +116,11 @@ export async function unenrollBatch(
     });
   }
 
-  if (errorCount > 0) {
-    appContextService
-      .getLogger()
-      .info(
-        `Skipping ${errorCount} agents, as failed validation (cannot unenroll from a hosted policy or already unenrolled)`
-      );
-
-    // writing out error result for those agents that failed validation, so the action is not going to stay in progress forever
-    await bulkCreateAgentActionResults(
-      esClient,
-      Object.keys(outgoingErrors).map((agentId) => ({
-        agentId,
-        actionId,
-        error: outgoingErrors[agentId].message,
-      }))
-    );
-  }
-
-  // Update the necessary agents
-  const updateData = options.revoke
-    ? { unenrolled_at: now, active: false }
-    : { unenrollment_started_at: now };
-
-  await bulkUpdateAgents(
+  await createErrorActionResults(
     esClient,
-    agentsToUpdate.map(({ id }) => ({ agentId: id, data: updateData }))
+    actionId,
+    outgoingErrors,
+    'cannot unenroll from a hosted policy or already unenrolled'
   );
 
   return {
diff --git a/x-pack/plugins/fleet/server/services/agents/update_agent_tags_action_runner.ts b/x-pack/plugins/fleet/server/services/agents/update_agent_tags_action_runner.ts
index 48f7b455d36b7..11d42bc76e39a 100644
--- a/x-pack/plugins/fleet/server/services/agents/update_agent_tags_action_runner.ts
+++ b/x-pack/plugins/fleet/server/services/agents/update_agent_tags_action_runner.ts
@@ -11,14 +11,16 @@ import { difference, uniq } from 'lodash';
 
 import type { Agent } from '../../types';
 
-import { appContextService } from '../app_context';
-
 import { ActionRunner } from './action_runner';
 
 import { bulkUpdateAgents } from './crud';
 import { BulkActionTaskType } from './bulk_actions_resolver';
 import { filterHostedPolicies } from './filter_hosted_agents';
-import { bulkCreateAgentActionResults, createAgentAction } from './actions';
+import {
+  createErrorActionResults,
+  bulkCreateAgentActionResults,
+  createAgentAction,
+} from './actions';
 
 export class UpdateAgentTagsActionRunner extends ActionRunner {
   protected async processAgents(agents: Agent[]): Promise<{ actionId: string }> {
@@ -90,12 +92,12 @@ export async function updateTagsBatch(
       data: {
         tags: getNewTags(agent),
       },
-    }))
+    })),
+    errors
   );
 
   const actionId = options.actionId ?? uuid();
   const total = options.total ?? givenAgents.length;
-  const errorCount = Object.keys(errors).length;
 
   // creating an action doc so that update tags  shows up in activity
   await createAgentAction(esClient, {
@@ -113,23 +115,12 @@ export async function updateTagsBatch(
     }))
   );
 
-  if (errorCount > 0) {
-    appContextService
-      .getLogger()
-      .info(
-        `Skipping ${errorCount} agents, as failed validation (cannot modified tags on hosted agents)`
-      );
-
-    // writing out error result for those agents that failed validation, so the action is not going to stay in progress forever
-    await bulkCreateAgentActionResults(
-      esClient,
-      Object.keys(errors).map((agentId) => ({
-        agentId,
-        actionId,
-        error: errors[agentId].message,
-      }))
-    );
-  }
+  await createErrorActionResults(
+    esClient,
+    actionId,
+    errors,
+    'cannot modified tags on hosted agents'
+  );
 
   return { actionId };
 }
diff --git a/x-pack/plugins/fleet/server/services/agents/upgrade.test.ts b/x-pack/plugins/fleet/server/services/agents/upgrade.test.ts
index db880f56ef474..8b888126ce114 100644
--- a/x-pack/plugins/fleet/server/services/agents/upgrade.test.ts
+++ b/x-pack/plugins/fleet/server/services/agents/upgrade.test.ts
@@ -50,7 +50,7 @@ describe('sendUpgradeAgentsActions (plural)', () => {
 
     // calls ES update with correct values
     const onlyRegular = [agentInRegularDoc._id, agentInRegularDoc2._id];
-    const calledWith = esClient.bulk.mock.calls[1][0];
+    const calledWith = esClient.bulk.mock.calls[0][0];
     const ids = (calledWith as estypes.BulkRequest)?.body
       ?.filter((i: any) => i.update !== undefined)
       .map((i: any) => i.update._id);
@@ -64,7 +64,7 @@ describe('sendUpgradeAgentsActions (plural)', () => {
     }
 
     // hosted policy is updated in action results with error
-    const calledWithActionResults = esClient.bulk.mock.calls[0][0] as estypes.BulkRequest;
+    const calledWithActionResults = esClient.bulk.mock.calls[1][0] as estypes.BulkRequest;
     // bulk write two line per create
     expect(calledWithActionResults.body?.length).toBe(2);
     const expectedObject = expect.objectContaining({
diff --git a/x-pack/plugins/fleet/server/services/agents/upgrade_action_runner.ts b/x-pack/plugins/fleet/server/services/agents/upgrade_action_runner.ts
index a34f189871a39..c6794de6e2dcb 100644
--- a/x-pack/plugins/fleet/server/services/agents/upgrade_action_runner.ts
+++ b/x-pack/plugins/fleet/server/services/agents/upgrade_action_runner.ts
@@ -22,7 +22,7 @@ import { ActionRunner } from './action_runner';
 
 import type { GetAgentsOptions } from './crud';
 import { bulkUpdateAgents } from './crud';
-import { bulkCreateAgentActionResults, createAgentAction } from './actions';
+import { createErrorActionResults, createAgentAction } from './actions';
 import { getHostedPolicies, isHostedAgent } from './hosted_agent';
 import { BulkActionTaskType } from './bulk_actions_resolver';
 
@@ -108,9 +108,20 @@ export async function upgradeBatch(
     options.upgradeDurationSeconds
   );
 
+  await bulkUpdateAgents(
+    esClient,
+    agentsToUpdate.map((agent) => ({
+      agentId: agent.id,
+      data: {
+        upgraded_at: null,
+        upgrade_started_at: now,
+      },
+    })),
+    errors
+  );
+
   const actionId = options.actionId ?? uuid();
-  const errorCount = Object.keys(errors).length;
-  const total = options.total ?? agentsToUpdate.length + errorCount;
+  const total = options.total ?? givenAgents.length;
 
   await createAgentAction(esClient, {
     id: actionId,
@@ -123,33 +134,11 @@ export async function upgradeBatch(
     ...rollingUpgradeOptions,
   });
 
-  if (errorCount > 0) {
-    appContextService
-      .getLogger()
-      .info(
-        `Skipping ${errorCount} agents, as failed validation (cannot upgrade hosted agent or agent not upgradeable)`
-      );
-
-    // writing out error result for those agents that failed validation, so the action is not going to stay in progress forever
-    await bulkCreateAgentActionResults(
-      esClient,
-      Object.keys(errors).map((agentId) => ({
-        agentId,
-        actionId,
-        error: errors[agentId].message,
-      }))
-    );
-  }
-
-  await bulkUpdateAgents(
+  await createErrorActionResults(
     esClient,
-    agentsToUpdate.map((agent) => ({
-      agentId: agent.id,
-      data: {
-        upgraded_at: null,
-        upgrade_started_at: now,
-      },
-    }))
+    actionId,
+    errors,
+    'cannot upgrade hosted agent or agent not upgradeable'
   );
 
   return {