diff --git a/src/cli/auth.rs b/src/cli/auth.rs
index 018ac3d..d1364d7 100644
--- a/src/cli/auth.rs
+++ b/src/cli/auth.rs
@@ -1,4 +1,4 @@
-use anyhow::Result;
+use anyhow::{Context, Result};
 use dialoguer::{Input, Password};
 
 use crate::api::auth;
@@ -9,11 +9,13 @@ use crate::output;
 pub async fn login_token() -> Result<()> {
     let email: String = dialoguer::Input::new()
         .with_prompt("Jira email")
-        .interact_text()?;
+        .interact_text()
+        .context("failed to read Jira email")?;
 
     let token: String = dialoguer::Password::new()
         .with_prompt("API token")
-        .interact()?;
+        .interact()
+        .context("failed to read API token")?;
 
     auth::store_api_token(&email, &token)?;
     println!("Credentials stored in keychain.");
@@ -28,11 +30,13 @@ pub async fn login_oauth() -> Result<()> {
 
     let client_id: String = Input::new()
         .with_prompt("OAuth Client ID")
-        .interact_text()?;
+        .interact_text()
+        .context("failed to read OAuth client ID")?;
 
     let client_secret: String = Password::new()
         .with_prompt("OAuth Client Secret")
-        .interact()?;
+        .interact()
+        .context("failed to read OAuth client secret")?;
 
     // Store OAuth app credentials in keychain
     crate::api::auth::store_oauth_app_credentials(&client_id, &client_secret)?;
diff --git a/src/cli/init.rs b/src/cli/init.rs
index 04560fc..8ba9e6b 100644
--- a/src/cli/init.rs
+++ b/src/cli/init.rs
@@ -1,4 +1,4 @@
-use anyhow::Result;
+use anyhow::{Context, Result};
 use dialoguer::{Confirm, Input, Select};
 
 use crate::config::{
@@ -12,7 +12,8 @@ pub async fn handle() -> Result<()> {
     // Step 1: Instance URL
     let url: String = Input::new()
         .with_prompt("Jira instance URL (e.g., https://yourorg.atlassian.net)")
-        .interact_text()?;
+        .interact_text()
+        .context("failed to read Jira instance URL")?;
     let url = url.trim_end_matches('/').to_string();
 
     // Step 2: Auth method
@@ -21,7 +22,8 @@ pub async fn handle() -> Result<()> {
         .with_prompt("Authentication method")
         .items(&auth_methods)
         .default(0)
-        .interact()?;
+        .interact()
+        .context("failed to prompt for authentication method")?;
 
     let global = GlobalConfig {
         instance: InstanceConfig {
@@ -58,7 +60,8 @@ pub async fn handle() -> Result<()> {
     let setup_project = Confirm::new()
         .with_prompt("Configure this directory as a Jira project?")
         .default(true)
-        .interact()?;
+        .interact()
+        .context("failed to prompt for project setup")?;
 
     if setup_project {
         let boards = client.list_boards(None, None).await?;
@@ -72,10 +75,14 @@ pub async fn handle() -> Result<()> {
             let board_choice = Select::new()
                 .with_prompt("Select board")
                 .items(&board_names)
-                .interact()?;
+                .interact()
+                .context("failed to prompt for board selection")?;
             let selected_board = &boards[board_choice];
 
-            let project_key: String = Input::new().with_prompt("Project key").interact_text()?;
+            let project_key: String = Input::new()
+                .with_prompt("Project key")
+                .interact_text()
+                .context("failed to read project key")?;
 
             let project_config = format!(
                 "project = \"{}\"\nboard_id = {}\n",
@@ -118,7 +125,8 @@ pub async fn handle() -> Result<()> {
                     let selection = Select::new()
                         .with_prompt("Multiple story points fields found. Select one")
                         .items(&names)
-                        .interact()?;
+                        .interact()
+                        .context("failed to prompt for story points field selection")?;
                     Some(matches[selection].0.clone())
                 }
             };
diff --git a/src/cli/issue/helpers.rs b/src/cli/issue/helpers.rs
index 7ca06eb..f574930 100644
--- a/src/cli/issue/helpers.rs
+++ b/src/cli/issue/helpers.rs
@@ -1,4 +1,4 @@
-use anyhow::Result;
+use anyhow::{Context, Result};
 
 use crate::api::client::JiraClient;
 use crate::config::Config;
@@ -67,7 +67,8 @@ pub(super) async fn resolve_team_field(
             let selection = dialoguer::Select::new()
                 .with_prompt(format!("Multiple teams named \"{}\"", team_name))
                 .items(&labels)
-                .interact()?;
+                .interact()
+                .context("failed to prompt for team selection")?;
             Ok((field_id, duplicates[selection].id.clone()))
         }
         crate::partial_match::MatchResult::Ambiguous(matches) => {
@@ -82,7 +83,8 @@ pub(super) async fn resolve_team_field(
             let selection = dialoguer::Select::new()
                 .with_prompt(format!("Multiple teams match \"{team_name}\""))
                 .items(&matches)
-                .interact()?;
+                .interact()
+                .context("failed to prompt for team selection")?;
             let selected_name = &matches[selection];
             let idx = teams
                 .iter()
@@ -115,7 +117,8 @@ pub(super) fn resolve_story_points_field_id(config: &Config) -> Result<String> {
 pub(super) fn prompt_input(prompt: &str) -> Result<String> {
     let input: String = dialoguer::Input::new()
         .with_prompt(prompt)
-        .interact_text()?;
+        .interact_text()
+        .with_context(|| format!("failed to read {}", prompt))?;
     Ok(input)
 }
 
@@ -197,7 +200,8 @@ fn disambiguate_user(
             let selection = dialoguer::Select::new()
                 .with_prompt(format!("Multiple users named \"{}\"", name))
                 .items(&labels)
-                .interact()?;
+                .interact()
+                .context("failed to prompt for user selection")?;
             Ok((
                 duplicates[selection].account_id.clone(),
                 duplicates[selection].display_name.clone(),
@@ -214,7 +218,8 @@ fn disambiguate_user(
             let selection = dialoguer::Select::new()
                 .with_prompt(format!("Multiple users match \"{name}\""))
                 .items(&matches)
-                .interact()?;
+                .interact()
+                .context("failed to prompt for user selection")?;
             let selected_name = &matches[selection];
             let idx = users
                 .iter()
@@ -428,7 +433,8 @@ pub(super) async fn resolve_asset(
             let selection = dialoguer::Select::new()
                 .with_prompt(format!("Multiple assets match \"{}\"", input))
                 .items(&items)
-                .interact()?;
+                .interact()
+                .context("failed to prompt for asset selection")?;
             Ok(duplicates[selection].object_key.clone())
         }
         crate::partial_match::MatchResult::Ambiguous(matches) => {
@@ -456,7 +462,8 @@ pub(super) async fn resolve_asset(
             let selection = dialoguer::Select::new()
                 .with_prompt(format!("Multiple assets match \"{}\"", input))
                 .items(&items)
-                .interact()?;
+                .interact()
+                .context("failed to prompt for asset selection")?;
             Ok(filtered[selection].object_key.clone())
         }
         crate::partial_match::MatchResult::None(_) => {
diff --git a/src/cli/issue/links.rs b/src/cli/issue/links.rs
index 02fd783..4830fb3 100644
--- a/src/cli/issue/links.rs
+++ b/src/cli/issue/links.rs
@@ -1,5 +1,5 @@
 use super::json_output;
-use anyhow::{Result, bail};
+use anyhow::{Context, Result, bail};
 
 use crate::api::client::JiraClient;
 use crate::cli::{IssueCommand, OutputFormat};
@@ -74,7 +74,8 @@ pub(super) async fn handle_link(
             let selection = dialoguer::Select::new()
                 .with_prompt(format!("Multiple types match \"{link_type_name}\""))
                 .items(&matches)
-                .interact()?;
+                .interact()
+                .context("failed to prompt for link type selection")?;
             matches[selection].clone()
         }
         MatchResult::None(_) => {
@@ -143,7 +144,8 @@ pub(super) async fn handle_unlink(
                 let selection = dialoguer::Select::new()
                     .with_prompt(format!("Multiple types match \"{type_name}\""))
                     .items(&matches)
-                    .interact()?;
+                    .interact()
+                    .context("failed to prompt for link type selection")?;
                 matches[selection].clone()
             }
             MatchResult::None(_) => {