diff --git a/crates/goose-cli/src/session/mod.rs b/crates/goose-cli/src/session/mod.rs
index 9eab36b1..d980ba7c 100644
--- a/crates/goose-cli/src/session/mod.rs
+++ b/crates/goose-cli/src/session/mod.rs
@@ -16,8 +16,7 @@ pub use goose::session::Identifier;
 
 use anyhow::{Context, Result};
 use completion::GooseCompleter;
-use etcetera::choose_app_strategy;
-use etcetera::AppStrategy;
+use etcetera::{choose_app_strategy, AppStrategy};
 use goose::agents::extension::{Envs, ExtensionConfig};
 use goose::agents::{Agent, SessionConfig};
 use goose::config::Config;
@@ -26,9 +25,9 @@ use goose::session;
 use input::InputResult;
 use mcp_core::handler::ToolError;
 use mcp_core::prompt::PromptMessage;
-
 use mcp_core::protocol::JsonRpcMessage;
 use mcp_core::protocol::JsonRpcNotification;
+
 use rand::{distributions::Alphanumeric, Rng};
 use serde_json::Value;
 use std::collections::HashMap;
@@ -354,9 +353,10 @@ impl Session {
         // Create and use a global history file in ~/.config/goose directory
         // This allows command history to persist across different chat sessions
         // instead of being tied to each individual session's messages
-        let history_file = choose_app_strategy(crate::APP_STRATEGY.clone())
-            .expect("goose requires a home dir")
-            .in_config_dir("history.txt");
+        let strategy =
+            choose_app_strategy(crate::APP_STRATEGY.clone()).expect("goose requires a home dir");
+        let config_dir = strategy.config_dir();
+        let history_file = config_dir.join("history.txt");
 
         // Ensure config directory exists
         if let Some(parent) = history_file.parent() {
@@ -382,6 +382,9 @@ impl Session {
 
         output::display_greeting();
         loop {
+            // Display context usage before each prompt
+            self.display_context_usage().await?;
+
             match input::get_input(&mut editor)? {
                 input::InputResult::Message(content) => {
                     match self.run_mode {
@@ -1118,6 +1121,26 @@ impl Session {
         Ok(metadata.total_tokens)
     }
 
+    /// Display enhanced context usage with session totals
+    pub async fn display_context_usage(&self) -> Result<()> {
+        let provider = self.agent.provider().await?;
+        let model_config = provider.get_model_config();
+        let context_limit = model_config.context_limit.unwrap_or(32000);
+
+        match self.get_metadata() {
+            Ok(metadata) => {
+                let total_tokens = metadata.total_tokens.unwrap_or(0) as usize;
+
+                output::display_context_usage(total_tokens, context_limit);
+            }
+            Err(_) => {
+                output::display_context_usage(0, context_limit);
+            }
+        }
+
+        Ok(())
+    }
+
     /// Handle prompt command execution
     async fn handle_prompt_command(&mut self, opts: input::PromptCommandOptions) -> Result<()> {
         // name is required
diff --git a/crates/goose-cli/src/session/output.rs b/crates/goose-cli/src/session/output.rs
index 78b4eb76..3bda532b 100644
--- a/crates/goose-cli/src/session/output.rs
+++ b/crates/goose-cli/src/session/output.rs
@@ -574,6 +574,38 @@ pub fn display_greeting() {
     println!("\nGoose is running! Enter your instructions, or try asking what goose can do.\n");
 }
 
+/// Display context window usage with both current and session totals
+pub fn display_context_usage(total_tokens: usize, context_limit: usize) {
+    use console::style;
+
+    // Calculate percentage used
+    let percentage = (total_tokens as f64 / context_limit as f64 * 100.0).round() as usize;
+
+    // Create dot visualization
+    let dot_count = 10;
+    let filled_dots = ((percentage as f64 / 100.0) * dot_count as f64).round() as usize;
+    let empty_dots = dot_count - filled_dots;
+
+    let filled = "●".repeat(filled_dots);
+    let empty = "○".repeat(empty_dots);
+
+    // Combine dots and apply color
+    let dots = format!("{}{}", filled, empty);
+    let colored_dots = if percentage < 50 {
+        style(dots).green()
+    } else if percentage < 85 {
+        style(dots).yellow()
+    } else {
+        style(dots).red()
+    };
+
+    // Print the status line
+    println!(
+        "Context: {} {}% ({}/{} tokens)",
+        colored_dots, percentage, total_tokens, context_limit
+    );
+}
+
 pub struct McpSpinners {
     bars: HashMap<String, ProgressBar>,
     log_spinner: Option<ProgressBar>,