diff --git a/x-pack/plugins/ingest_manager/server/services/agents/enroll.test.ts b/x-pack/plugins/ingest_manager/server/services/agents/enroll.test.ts
index 764564cfa49f5..44473bf2d8d79 100644
--- a/x-pack/plugins/ingest_manager/server/services/agents/enroll.test.ts
+++ b/x-pack/plugins/ingest_manager/server/services/agents/enroll.test.ts
@@ -5,62 +5,52 @@
  */
 
 import { validateAgentVersion } from './enroll';
-import { appContextService } from '../app_context';
-import { IngestManagerAppContext } from '../../plugin';
 
 describe('validateAgentVersion', () => {
   it('should throw with agent > kibana version', () => {
-    appContextService.start(({
-      kibanaVersion: '8.0.0',
-    } as unknown) as IngestManagerAppContext);
-    expect(() =>
-      validateAgentVersion({
-        local: { elastic: { agent: { version: '8.8.0' } } },
-        userProvided: {},
-      })
-    ).toThrowError(/Agent version is not compatible with kibana version/);
+    expect(() => validateAgentVersion('8.8.0', '8.0.0')).toThrowError('not compatible');
   });
   it('should work with agent < kibana version', () => {
-    appContextService.start(({
-      kibanaVersion: '8.0.0',
-    } as unknown) as IngestManagerAppContext);
-    validateAgentVersion({ local: { elastic: { agent: { version: '7.8.0' } } }, userProvided: {} });
+    validateAgentVersion('7.8.0', '8.0.0');
   });
 
   it('should work with agent = kibana version', () => {
-    appContextService.start(({
-      kibanaVersion: '8.0.0',
-    } as unknown) as IngestManagerAppContext);
-    validateAgentVersion({ local: { elastic: { agent: { version: '8.0.0' } } }, userProvided: {} });
+    validateAgentVersion('8.0.0', '8.0.0');
   });
 
   it('should work with SNAPSHOT version', () => {
-    appContextService.start(({
-      kibanaVersion: '8.0.0-SNAPSHOT',
-    } as unknown) as IngestManagerAppContext);
-    validateAgentVersion({
-      local: { elastic: { agent: { version: '8.0.0-SNAPSHOT' } } },
-      userProvided: {},
-    });
+    validateAgentVersion('8.0.0-SNAPSHOT', '8.0.0-SNAPSHOT');
   });
 
   it('should work with a agent using SNAPSHOT version', () => {
-    appContextService.start(({
-      kibanaVersion: '7.8.0',
-    } as unknown) as IngestManagerAppContext);
-    validateAgentVersion({
-      local: { elastic: { agent: { version: '7.8.0-SNAPSHOT' } } },
-      userProvided: {},
-    });
+    validateAgentVersion('7.8.0-SNAPSHOT', '7.8.0');
   });
 
   it('should work with a kibana using SNAPSHOT version', () => {
-    appContextService.start(({
-      kibanaVersion: '7.8.0-SNAPSHOT',
-    } as unknown) as IngestManagerAppContext);
-    validateAgentVersion({
-      local: { elastic: { agent: { version: '7.8.0' } } },
-      userProvided: {},
-    });
+    validateAgentVersion('7.8.0', '7.8.0-SNAPSHOT');
+  });
+
+  it('very close versions, e.g. patch/prerelease - all combos should work', () => {
+    validateAgentVersion('7.9.1', '7.9.2');
+    validateAgentVersion('7.8.1', '7.8.2');
+    validateAgentVersion('7.6.99', '7.6.2');
+    validateAgentVersion('7.6.2', '7.6.99');
+    validateAgentVersion('5.94.3', '5.94.1234-SNAPSHOT');
+    validateAgentVersion('5.94.3-SNAPSHOT', '5.94.1');
+  });
+
+  it('somewhat close versions, minor release is 1 or 2 versions back and is older than the stack', () => {
+    validateAgentVersion('7.9.1', '7.10.2');
+    validateAgentVersion('7.9.9', '7.11.1');
+    validateAgentVersion('7.6.99', '7.6.2');
+    validateAgentVersion('7.6.2', '7.6.99');
+    expect(() => validateAgentVersion('5.94.3-SNAPSHOT', '5.93.1')).toThrowError('not compatible');
+    expect(() => validateAgentVersion('5.94.3', '5.92.99-SNAPSHOT')).toThrowError('not compatible');
+  });
+
+  it('versions where Agent is a minor version or major version greater (newer) than the stack should not work', () => {
+    expect(() => validateAgentVersion('7.10.1', '7.9.99')).toThrowError('not compatible');
+    expect(() => validateAgentVersion('7.9.9', '6.11.1')).toThrowError('not compatible');
+    expect(() => validateAgentVersion('5.94.3', '5.92.99-SNAPSHOT')).toThrowError('not compatible');
   });
 });
diff --git a/x-pack/plugins/ingest_manager/server/services/agents/enroll.ts b/x-pack/plugins/ingest_manager/server/services/agents/enroll.ts
index b63b1c13e4df9..121cf50186caa 100644
--- a/x-pack/plugins/ingest_manager/server/services/agents/enroll.ts
+++ b/x-pack/plugins/ingest_manager/server/services/agents/enroll.ts
@@ -20,7 +20,8 @@ export async function enroll(
   metadata?: { local: any; userProvided: any },
   sharedId?: string
 ): Promise<Agent> {
-  validateAgentVersion(metadata);
+  const agentVersion = metadata?.local?.elastic?.agent?.version;
+  validateAgentVersion(agentVersion);
 
   const existingAgent = sharedId ? await getAgentBySharedId(soClient, sharedId) : null;
 
@@ -89,24 +90,50 @@ async function getAgentBySharedId(soClient: SavedObjectsClientContract, sharedId
   return null;
 }
 
-export function validateAgentVersion(metadata?: { local: any; userProvided: any }) {
-  const kibanaVersion = semver.parse(appContextService.getKibanaVersion());
-  if (!kibanaVersion) {
-    throw Boom.badRequest('Kibana version is not set');
-  }
-  const version = semver.parse(metadata?.local?.elastic?.agent?.version);
-  if (!version) {
-    throw Boom.badRequest('Agent version not provided in metadata.');
+export function validateAgentVersion(
+  agentVersion: string,
+  kibanaVersion = appContextService.getKibanaVersion()
+) {
+  const agentVersionParsed = semver.parse(agentVersion);
+  if (!agentVersionParsed) {
+    throw Boom.badRequest('Agent version not provided');
   }
 
-  if (!version || !semver.lte(formatVersion(version), formatVersion(kibanaVersion))) {
-    throw Boom.badRequest('Agent version is not compatible with kibana version');
+  const kibanaVersionParsed = semver.parse(kibanaVersion);
+  if (!kibanaVersionParsed) {
+    throw Boom.badRequest('Kibana version is not set or provided');
   }
-}
 
-/**
- * used to remove prelease from version as includePrerelease in not working as expected
- */
-function formatVersion(version: semver.SemVer) {
-  return `${version.major}.${version.minor}.${version.patch}`;
+  const diff = semver.diff(agentVersion, kibanaVersion);
+  switch (diff) {
+    // section 1) very close versions, only patch release differences - all combos should work
+    // Agent a.b.1 < Kibana a.b.2
+    // Agent a.b.2 > Kibana a.b.1
+    case null:
+    case 'prerelease':
+    case 'prepatch':
+    case 'patch':
+      return; // OK
+
+    // section 2) somewhat close versions, Agent minor release is 1 or 2 versions back and is older than the stack:
+    // Agent a.9.x < Kibana a.10.x
+    // Agent a.9.x < Kibana a.11.x
+    case 'preminor':
+    case 'minor':
+      if (
+        agentVersionParsed.minor < kibanaVersionParsed.minor &&
+        kibanaVersionParsed.minor - agentVersionParsed.minor <= 2
+      )
+        return;
+
+    // section 3) versions where Agent is a minor version or major version greater (newer) than the stack should not work:
+    // Agent 7.10.x > Kibana 7.9.x
+    // Agent 8.0.x > Kibana 7.9.x
+    default:
+      if (semver.lte(agentVersionParsed, kibanaVersionParsed)) return;
+      else
+        throw Boom.badRequest(
+          `Agent version ${agentVersion} is not compatible with Kibana version ${kibanaVersion}`
+        );
+  }
 }
diff --git a/x-pack/test/ingest_manager_api_integration/apis/fleet/agents/enroll.ts b/x-pack/test/ingest_manager_api_integration/apis/fleet/agents/enroll.ts
index 4689ca805d8de..fa6b455eb8f9e 100644
--- a/x-pack/test/ingest_manager_api_integration/apis/fleet/agents/enroll.ts
+++ b/x-pack/test/ingest_manager_api_integration/apis/fleet/agents/enroll.ts
@@ -115,7 +115,7 @@ export default function (providerContext: FtrProviderContext) {
           },
         })
         .expect(400);
-      expect(apiResponse.message).to.match(/Agent version is not compatible with kibana/);
+      expect(apiResponse.message).to.match(/is not compatible/);
     });
 
     it('should allow to enroll an agent with a valid enrollment token', async () => {