diff --git a/src-tauri/src/config.rs b/src-tauri/src/config.rs
index 29fc620..00cd3bd 100644
--- a/src-tauri/src/config.rs
+++ b/src-tauri/src/config.rs
@@ -40,6 +40,16 @@ pub struct HikariConfig {
 
     #[serde(default)]
     pub theme: Theme,
+
+    #[serde(default = "default_greeting_enabled")]
+    pub greeting_enabled: bool,
+
+    #[serde(default)]
+    pub greeting_custom_prompt: Option<String>,
+}
+
+fn default_greeting_enabled() -> bool {
+    true
 }
 
 #[derive(Debug, Clone, Serialize, Deserialize, Default, PartialEq)]
@@ -63,6 +73,8 @@ mod tests {
         assert!(config.mcp_servers_json.is_none());
         assert!(config.auto_granted_tools.is_empty());
         assert_eq!(config.theme, Theme::Dark);
+        assert!(!config.greeting_enabled);
+        assert!(config.greeting_custom_prompt.is_none());
     }
 
     #[test]
@@ -74,6 +86,8 @@ mod tests {
             mcp_servers_json: None,
             auto_granted_tools: vec!["Read".to_string(), "Glob".to_string()],
             theme: Theme::Light,
+            greeting_enabled: true,
+            greeting_custom_prompt: Some("Hello!".to_string()),
         };
 
         let json = serde_json::to_string(&config).unwrap();
@@ -83,6 +97,8 @@ mod tests {
         assert_eq!(deserialized.custom_instructions, config.custom_instructions);
         assert_eq!(deserialized.auto_granted_tools, config.auto_granted_tools);
         assert_eq!(deserialized.theme, Theme::Light);
+        assert!(deserialized.greeting_enabled);
+        assert_eq!(deserialized.greeting_custom_prompt, Some("Hello!".to_string()));
     }
 
     #[test]
diff --git a/src/lib/components/ConfigSidebar.svelte b/src/lib/components/ConfigSidebar.svelte
index bb09d8c..fe53587 100644
--- a/src/lib/components/ConfigSidebar.svelte
+++ b/src/lib/components/ConfigSidebar.svelte
@@ -9,6 +9,8 @@
     mcp_servers_json: null,
     auto_granted_tools: [],
     theme: "dark",
+    greeting_enabled: true,
+    greeting_custom_prompt: null,
   });
 
   let isOpen = $state(false);
@@ -220,6 +222,44 @@
       </div>
     </section>
 
+    <!-- Greeting Section -->
+    <section class="mb-6">
+      <h3 class="text-sm font-medium text-[var(--accent-primary)] uppercase tracking-wider mb-3">
+        Greeting
+      </h3>
+
+      <!-- Enable/Disable Toggle -->
+      <div class="mb-4">
+        <label class="flex items-center gap-3 cursor-pointer">
+          <input
+            type="checkbox"
+            bind:checked={config.greeting_enabled}
+            class="w-4 h-4 rounded border-[var(--border-color)] bg-[var(--bg-primary)] text-[var(--accent-primary)] focus:ring-[var(--accent-primary)]"
+          />
+          <span class="text-sm text-gray-300">Send greeting on connect</span>
+        </label>
+        <p class="text-xs text-gray-500 mt-1 ml-7">
+          Automatically greet you when a session starts with time-based messages
+        </p>
+      </div>
+
+      <!-- Custom Greeting Prompt -->
+      {#if config.greeting_enabled}
+        <div class="mb-4">
+          <label for="greeting-prompt" class="block text-sm text-gray-400 mb-1">
+            Custom Greeting Prompt <span class="text-gray-600">(optional)</span>
+          </label>
+          <textarea
+            id="greeting-prompt"
+            bind:value={config.greeting_custom_prompt}
+            rows="3"
+            placeholder="Leave empty for time-based greetings, or customize how you'd like to be greeted..."
+            class="w-full px-3 py-2 bg-[var(--bg-primary)] border border-[var(--border-color)] rounded-lg text-[var(--text-primary)] focus:outline-none focus:border-[var(--accent-primary)] resize-none"
+          ></textarea>
+        </div>
+      {/if}
+    </section>
+
     <!-- MCP Servers Section -->
     <section class="mb-6">
       <h3 class="text-sm font-medium text-[var(--accent-primary)] uppercase tracking-wider mb-3">
diff --git a/src/lib/stores/config.ts b/src/lib/stores/config.ts
index 2a2d63a..7d5aa45 100644
--- a/src/lib/stores/config.ts
+++ b/src/lib/stores/config.ts
@@ -10,6 +10,8 @@ export interface HikariConfig {
   mcp_servers_json: string | null;
   auto_granted_tools: string[];
   theme: Theme;
+  greeting_enabled: boolean;
+  greeting_custom_prompt: string | null;
 }
 
 const defaultConfig: HikariConfig = {
@@ -19,6 +21,8 @@ const defaultConfig: HikariConfig = {
   mcp_servers_json: null,
   auto_granted_tools: [],
   theme: "dark",
+  greeting_enabled: true,
+  greeting_custom_prompt: null,
 };
 
 function createConfigStore() {
diff --git a/src/lib/tauri.ts b/src/lib/tauri.ts
index bc0cd4f..5688590 100644
--- a/src/lib/tauri.ts
+++ b/src/lib/tauri.ts
@@ -1,6 +1,8 @@
 import { listen } from "@tauri-apps/api/event";
+import { invoke } from "@tauri-apps/api/core";
 import { claudeStore } from "$lib/stores/claude";
 import { characterState } from "$lib/stores/character";
+import { configStore } from "$lib/stores/config";
 import type { ConnectionStatus, PermissionPromptEvent } from "$lib/types/messages";
 import type { CharacterState } from "$lib/types/states";
 
@@ -9,6 +11,36 @@ interface StateChangePayload {
   tool_name: string | null;
 }
 
+function generateTimeBasedGreeting(): string {
+  const hour = new Date().getHours();
+
+  if (hour >= 5 && hour < 12) {
+    return "Good morning! How can I help you today?";
+  } else if (hour >= 12 && hour < 17) {
+    return "Good afternoon! What are we working on?";
+  } else if (hour >= 17 && hour < 21) {
+    return "Good evening! Ready to get some work done?";
+  } else {
+    return "Working late? I'm here to help!";
+  }
+}
+
+async function sendGreeting() {
+  const config = configStore.getConfig();
+
+  if (!config.greeting_enabled) {
+    return;
+  }
+
+  const greetingPrompt = config.greeting_custom_prompt?.trim() || generateTimeBasedGreeting();
+
+  try {
+    await invoke("send_prompt", { message: greetingPrompt });
+  } catch (error) {
+    console.error("Failed to send greeting:", error);
+  }
+}
+
 interface OutputPayload {
   line_type: string;
   content: string;
@@ -69,9 +101,11 @@ export async function initializeTauriListeners() {
     // no-op
   });
 
-  await listen<string>("claude:session", (event) => {
+  await listen<string>("claude:session", async (event) => {
     claudeStore.setSessionId(event.payload);
     claudeStore.addLine("system", `Session: ${event.payload.substring(0, 8)}...`);
+
+    await sendGreeting();
   });
 
   await listen<string>("claude:cwd", (event) => {