diff --git a/changelog.d/114.added.md b/changelog.d/114.added.md
new file mode 100644
index 00000000..cf1ef1c5
--- /dev/null
+++ b/changelog.d/114.added.md
@@ -0,0 +1 @@
+Users will be invited to join the Discord server after 10 usages
\ No newline at end of file
diff --git a/package.json b/package.json
index 864e4d5e..c59cda5f 100644
--- a/package.json
+++ b/package.json
@@ -115,7 +115,12 @@
 				"mirrord.promptReview": {
 					"type": "boolean",
 					"default": true,
-					"description": "Occasionally show a notification asking for plugin review"
+					"description": "Occasionally show a notification asking for plugin review."
+				},
+				"mirrord.promptDiscord": {
+					"type": "boolean",
+					"default": true,
+					"description": "Show a notification inviting the user to the Discord server."
 				},
 				"mirrord.promptAgentVersionMismatch": {
 					"type": "boolean",
@@ -131,9 +136,12 @@
 					"description": "Path to local mirrord installation."
 				},
 				"mirrord.autoUpdate": {
-					"type": ["string", "boolean"],
+					"type": [
+						"string",
+						"boolean"
+					],
 					"default": true,
-					"description": "Automatically update mirrord binary."					
+					"description": "Automatically update mirrord binary."
 				}
 			}
 		},
@@ -163,7 +171,10 @@
 		},
 		"jsonValidation": [
 			{
-				"fileMatch": ["*mirrord.json", "*.mirrord/*.json"],
+				"fileMatch": [
+					"*mirrord.json",
+					"*.mirrord/*.json"
+				],
 				"url": "https://raw.githubusercontent.com/metalbear-co/mirrord/latest/mirrord-schema.json"
 			}
 		],
@@ -246,4 +257,4 @@
 		"which": "^3.0.1",
 		"yaml": "^2.1.3"
 	}
-}
+}
\ No newline at end of file
diff --git a/src/api.ts b/src/api.ts
index e76a81ec..c8d1be8b 100644
--- a/src/api.ts
+++ b/src/api.ts
@@ -17,6 +17,16 @@ const FEEDBACK_COUNTER = 'mirrord-feedback-counter';
 */
 const FEEDBACK_COUNTER_REVIEW_AFTER = 100;
 
+/**
+* Key to access the feedback counter (see `tickDiscordCounter`) from the global user config.
+*/
+const DISCORD_COUNTER = 'mirrord-discord-counter';
+
+/**
+* Amount of times we run mirrord before inviting the user to join the Discord server.
+*/
+const DISCORD_COUNTER_PROMPT_AFTER = 10;
+
 const TARGET_TYPE_DISPLAY: Record<string, string> = {
   pod: 'Pod',
   deployment: 'Deployment',
@@ -378,6 +388,7 @@ export class MirrordAPI {
   async binaryExecute(target: string | null, configFile: string | null, executable: string | null, configEnv: EnvVars): Promise<MirrordExecution> {
     tickMirrordForTeamsCounter();
     tickFeedbackCounter();
+    tickDiscordCounter();
 
     /// Create a promise that resolves when the mirrord process exits
     return await vscode.window.withProgress({
@@ -543,3 +554,24 @@ function tickFeedbackCounter() {
       .info();
   }
 }
+
+/**
+* Updates the global Discord counter.
+* After `DISCORD_COUNTER_PROMPT_AFTER` mirrord runs, displays a message asking the user to join the discord.
+*/
+function tickDiscordCounter() {
+  const previousRuns = parseInt(globalContext.globalState.get(DISCORD_COUNTER) ?? '0');
+  const currentRuns = previousRuns + 1;
+
+  globalContext.globalState.update(DISCORD_COUNTER, currentRuns);
+
+  if ((currentRuns - DISCORD_COUNTER_PROMPT_AFTER) === 0) {
+    new NotificationBuilder()
+      .withMessage(`Need any help with mirrord? Come chat with our team on Discord!`)
+      .withGenericAction("Join us!", async () => {
+        vscode.commands.executeCommand(MirrordStatus.joinDiscordCommandId);
+      })
+      .withDisableAction('promptDiscord')
+      .info();
+  }
+}
\ No newline at end of file