diff --git a/x-pack/plugins/fleet/public/applications/fleet/components/fleet_server_instructions/hooks/use_wait_for_fleet_server.ts b/x-pack/plugins/fleet/public/applications/fleet/components/fleet_server_instructions/hooks/use_wait_for_fleet_server.ts
index 4da59560e408e..7721025a75067 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/components/fleet_server_instructions/hooks/use_wait_for_fleet_server.ts
+++ b/x-pack/plugins/fleet/public/applications/fleet/components/fleet_server_instructions/hooks/use_wait_for_fleet_server.ts
@@ -6,9 +6,9 @@
  */
 
 import { i18n } from '@kbn/i18n';
-import { useEffect, useState } from 'react';
+import { useEffect } from 'react';
 
-import { sendGetFleetStatus, useStartServices } from '../../../hooks';
+import { useFleetStatus, useStartServices } from '../../../hooks';
 
 const REFRESH_INTERVAL = 10000;
 
@@ -17,26 +17,25 @@ const REFRESH_INTERVAL = 10000;
  * in the `missing_requirements` list.
  */
 export const useWaitForFleetServer = () => {
-  const [isFleetServerReady, setIsFleetServerReady] = useState(false);
+  const fleetStatus = useFleetStatus();
   const { notifications } = useStartServices();
 
+  const isFleetServerReady =
+    fleetStatus.isReady && !fleetStatus.missingRequirements?.includes('fleet_server');
+
   useEffect(() => {
     let interval: ReturnType<typeof setInterval> | null = null;
 
     if (!isFleetServerReady) {
       interval = setInterval(async () => {
         try {
-          const res = await sendGetFleetStatus();
-
-          if (res.error) {
-            throw res.error;
-          }
-          if (res.data?.isReady && !res.data?.missing_requirements?.includes('fleet_server')) {
-            setIsFleetServerReady(true);
-
+          if (isFleetServerReady) {
             if (interval) {
               clearInterval(interval);
             }
+          } else {
+            fleetStatus.setForceDisplayInstructions(true);
+            fleetStatus.refresh();
           }
         } catch (err) {
           notifications.toasts.addError(err, {
@@ -55,7 +54,7 @@ export const useWaitForFleetServer = () => {
     };
 
     return cleanup;
-  }, [notifications.toasts, isFleetServerReady]);
+  }, [notifications.toasts, isFleetServerReady, fleetStatus]);
 
   return { isFleetServerReady };
 };
diff --git a/x-pack/plugins/fleet/public/applications/fleet/components/fleet_server_instructions/steps/confirm_fleet_server_connection.tsx b/x-pack/plugins/fleet/public/applications/fleet/components/fleet_server_instructions/steps/confirm_fleet_server_connection.tsx
index 15e8609191019..8111fd3f09ac6 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/components/fleet_server_instructions/steps/confirm_fleet_server_connection.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/components/fleet_server_instructions/steps/confirm_fleet_server_connection.tsx
@@ -13,7 +13,7 @@ import { EuiText } from '@elastic/eui';
 import { i18n } from '@kbn/i18n';
 import { FormattedMessage } from '@kbn/i18n-react';
 
-import { useFlyoutContext } from '../../../hooks';
+import { useFleetStatus, useFlyoutContext } from '../../../hooks';
 
 export function getConfirmFleetServerConnectionStep({
   disabled,
@@ -41,6 +41,12 @@ const ConfirmFleetServerConnectionStepContent: React.FunctionComponent<{
   isFleetServerReady: boolean;
 }> = ({ isFleetServerReady }) => {
   const flyoutContext = useFlyoutContext();
+  const fleetStatus = useFleetStatus();
+
+  const handleContinueClick = () => {
+    fleetStatus.forceDisplayInstructions = false;
+    flyoutContext.openEnrollmentFlyout();
+  };
 
   return isFleetServerReady ? (
     <>
@@ -53,7 +59,7 @@ const ConfirmFleetServerConnectionStepContent: React.FunctionComponent<{
 
       <EuiSpacer size="m" />
 
-      <EuiButton color="primary" onClick={flyoutContext.openEnrollmentFlyout}>
+      <EuiButton color="primary" onClick={handleContinueClick}>
         <FormattedMessage
           id="xpack.fleet.fleetServerFlyout.continueEnrollingButton"
           defaultMessage="Continue enrolling Elastic Agent"
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/index.test.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/index.test.tsx
index 35353b9aaae3d..7139cabed4f6f 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/index.test.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/index.test.tsx
@@ -69,6 +69,8 @@ describe('AgentApp', () => {
       enabled: true,
       isReady: false,
       refresh: async () => {},
+      forceDisplayInstructions: false,
+      setForceDisplayInstructions: () => {},
     });
     const { utils } = renderAgentsApp();
 
@@ -82,6 +84,8 @@ describe('AgentApp', () => {
       isReady: false,
       missingRequirements: ['api_keys'],
       refresh: async () => {},
+      forceDisplayInstructions: false,
+      setForceDisplayInstructions: () => {},
     });
     const { utils } = renderAgentsApp();
     expect(utils.queryByText('MissingESRequirementsPage')).not.toBeNull();
@@ -95,6 +99,8 @@ describe('AgentApp', () => {
       isReady: false,
       missingRequirements: ['fleet_server'],
       refresh: async () => {},
+      forceDisplayInstructions: false,
+      setForceDisplayInstructions: () => {},
     });
     const { utils } = renderAgentsApp();
     expect(utils.queryByText('FleetServerRequirementPage')).not.toBeNull();
@@ -109,6 +115,8 @@ describe('AgentApp', () => {
       missingRequirements: [],
       missingOptionalFeatures: ['encrypted_saved_object_encryption_key_required'],
       refresh: async () => {},
+      forceDisplayInstructions: false,
+      setForceDisplayInstructions: () => {},
     });
     const { utils } = renderAgentsApp();
 
diff --git a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/index.tsx b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/index.tsx
index 78ceb6293d3ce..ed770311ad9e9 100644
--- a/x-pack/plugins/fleet/public/applications/fleet/sections/agents/index.tsx
+++ b/x-pack/plugins/fleet/public/applications/fleet/sections/agents/index.tsx
@@ -75,6 +75,9 @@ export const AgentsApp: React.FunctionComponent = () => {
     fleetStatus?.missingRequirements?.length === 1 &&
     fleetStatus.missingRequirements[0] === 'fleet_server';
 
+  const displayInstructions =
+    fleetStatus.forceDisplayInstructions || hasOnlyFleetServerMissingRequirement;
+
   if (
     !hasOnlyFleetServerMissingRequirement &&
     fleetStatus.missingRequirements &&
@@ -86,7 +89,7 @@ export const AgentsApp: React.FunctionComponent = () => {
     return <NoAccessPage />;
   }
 
-  const rightColumn = hasOnlyFleetServerMissingRequirement ? (
+  const rightColumn = displayInstructions ? (
     <>
       <EuiFlexGroup justifyContent="flexEnd">
         <EuiFlexItem grow={false}>
@@ -114,7 +117,7 @@ export const AgentsApp: React.FunctionComponent = () => {
             {fleetServerModalVisible && (
               <FleetServerUpgradeModal onClose={onCloseFleetServerModal} />
             )}
-            {hasOnlyFleetServerMissingRequirement ? (
+            {displayInstructions ? (
               <FleetServerRequirementPage showEnrollmentRecommendation={false} />
             ) : (
               <AgentListPage />
diff --git a/x-pack/plugins/fleet/public/hooks/use_fleet_status.tsx b/x-pack/plugins/fleet/public/hooks/use_fleet_status.tsx
index b05df0c619e0a..7319cd9f07be7 100644
--- a/x-pack/plugins/fleet/public/hooks/use_fleet_status.tsx
+++ b/x-pack/plugins/fleet/public/hooks/use_fleet_status.tsx
@@ -23,17 +23,26 @@ interface FleetStatusState {
 
 interface FleetStatus extends FleetStatusState {
   refresh: () => Promise<void>;
+
+  // This flag allows us to opt into displaying the Fleet Server enrollment instructions even if
+  // a healthy Fleet Server has been detected, so we can delay removing the enrollment UI until
+  // some user action like clicking a "continue" button
+  forceDisplayInstructions: boolean;
+  setForceDisplayInstructions: React.Dispatch<boolean>;
 }
 
 const FleetStatusContext = React.createContext<FleetStatus | undefined>(undefined);
 
 export const FleetStatusProvider: React.FC = ({ children }) => {
   const config = useConfig();
+  const [forceDisplayInstructions, setForceDisplayInstructions] = useState(false);
+
   const [state, setState] = useState<FleetStatusState>({
     enabled: config.agents.enabled,
     isLoading: false,
     isReady: false,
   });
+
   const sendGetStatus = useCallback(
     async function sendGetStatus() {
       try {
@@ -64,7 +73,9 @@ export const FleetStatusProvider: React.FC = ({ children }) => {
   const refresh = useCallback(() => sendGetStatus(), [sendGetStatus]);
 
   return (
-    <FleetStatusContext.Provider value={{ ...state, refresh }}>
+    <FleetStatusContext.Provider
+      value={{ ...state, refresh, forceDisplayInstructions, setForceDisplayInstructions }}
+    >
       {children}
     </FleetStatusContext.Provider>
   );