diff --git a/crates/agent_ui/src/agent_panel.rs b/crates/agent_ui/src/agent_panel.rs
index 085e0d893d95fb441e919d4fb1f3683901c3c422..fe10a8a2373abcd05c650f0dc8d5378e68d1c50d 100644
--- a/crates/agent_ui/src/agent_panel.rs
+++ b/crates/agent_ui/src/agent_panel.rs
@@ -2256,6 +2256,16 @@ impl AgentPanel {
             }
         };
         self.start_thread_in = new_target;
+        let target = match &self.start_thread_in {
+            StartThreadIn::LocalProject => "current_worktree",
+            StartThreadIn::NewWorktree { .. } => "new_worktree",
+            StartThreadIn::LinkedWorktree { .. } => "linked_worktree",
+        };
+        telemetry::event!(
+            "Start Thread In Changed",
+            target = target,
+            side = agent_panel_side_str(cx)
+        );
         if let Some(thread) = self.active_thread_view(cx) {
             thread.update(cx, |thread, cx| thread.focus_handle(cx).focus(window, cx));
         }
@@ -3334,6 +3344,13 @@ fn agent_panel_dock_position(cx: &App) -> DockPosition {
     AgentSettings::get_global(cx).dock.into()
 }
 
+fn agent_panel_side_str(cx: &App) -> &'static str {
+    match agent_panel_dock_position(cx) {
+        DockPosition::Left => "left",
+        DockPosition::Right | DockPosition::Bottom => "right",
+    }
+}
+
 fn thread_location_str(cx: &App) -> &'static str {
     use settings::{NewThreadLocation, Settings};
     match AgentSettings::get_global(cx).new_thread_location {
diff --git a/crates/agent_ui/src/conversation_view.rs b/crates/agent_ui/src/conversation_view.rs
index 8d3d325f402e8568b31fd4cb4e3774be863643d1..bdd999746c5c752fedc484adb0b46a3fa68ae07f 100644
--- a/crates/agent_ui/src/conversation_view.rs
+++ b/crates/agent_ui/src/conversation_view.rs
@@ -669,6 +669,10 @@ impl ConversationView {
         let connect_result = connection_entry.read(cx).wait_for_connection();
 
         let load_session_id = resume_session_id.clone();
+        let side = match AgentSettings::get_global(cx).dock {
+            settings::DockPosition::Left => "left",
+            settings::DockPosition::Right | settings::DockPosition::Bottom => "right",
+        };
         let load_task = cx.spawn_in(window, async move |this, cx| {
             let (connection, history) = match connect_result.await {
                 Ok(AgentConnectedState {
@@ -685,7 +689,11 @@ impl ConversationView {
                 }
             };
 
-            telemetry::event!("Agent Thread Started", agent = connection.telemetry_id());
+            telemetry::event!(
+                "Agent Thread Started",
+                agent = connection.telemetry_id(),
+                side = side
+            );
 
             let mut resumed_without_history = false;
             let result = if let Some(session_id) = load_session_id.clone() {
diff --git a/crates/agent_ui/src/conversation_view/thread_view.rs b/crates/agent_ui/src/conversation_view/thread_view.rs
index ae9bf17c76bde99cdacea9d5bb205074a1a4ee39..22b1a6dab0cac92cbd0c79db5fcb0c5bd56a336b 100644
--- a/crates/agent_ui/src/conversation_view/thread_view.rs
+++ b/crates/agent_ui/src/conversation_view/thread_view.rs
@@ -13,7 +13,7 @@ use crate::message_editor::SharedSessionCapabilities;
 use gpui::{Corner, List};
 use heapless::Vec as ArrayVec;
 use language_model::{LanguageModelEffortLevel, Speed};
-use settings::update_settings_file;
+use settings::{DockPosition, update_settings_file};
 use ui::{ButtonLike, SpinnerLabel, SpinnerVariant, SplitButton, SplitButtonStyle, Tab};
 use workspace::SERIALIZATION_THROTTLE_TIME;
 
@@ -1066,6 +1066,10 @@ impl ThreadView {
         })
         .detach();
 
+        let side = match AgentSettings::get_global(cx).dock {
+            DockPosition::Left => "left",
+            DockPosition::Right | DockPosition::Bottom => "right",
+        };
         let task = cx.spawn_in(window, async move |this, cx| {
             let Some((contents, tracked_buffers)) = contents_task.await? else {
                 return Ok(());
@@ -1134,7 +1138,8 @@ impl ThreadView {
                     session = session_id,
                     parent_session_id = parent_session_id.as_ref().map(|id| id.to_string()),
                     model = model_id,
-                    mode = mode_id
+                    mode = mode_id,
+                    side = side
                 );
 
                 thread.send(contents, cx)
@@ -1163,6 +1168,7 @@ impl ThreadView {
                 mode = mode_id,
                 status,
                 turn_time_ms,
+                side = side
             );
             res.map(|_| ())
         });
diff --git a/crates/agent_ui/src/threads_archive_view.rs b/crates/agent_ui/src/threads_archive_view.rs
index 7cb8410e5017438b0e8adde673887c13397d9abf..e0a427f152912779b39ace42b8d04106a965a7fc 100644
--- a/crates/agent_ui/src/threads_archive_view.rs
+++ b/crates/agent_ui/src/threads_archive_view.rs
@@ -557,6 +557,11 @@ impl ThreadsArchiveView {
                     .on_click({
                         let thread = thread.clone();
                         cx.listener(move |this, _, window, cx| {
+                            let side = match AgentSettings::get_global(cx).sidebar_side() {
+                                settings::SidebarSide::Left => "left",
+                                settings::SidebarSide::Right => "right",
+                            };
+                            telemetry::event!("Archived Thread Opened", side = side);
                             this.unarchive_thread(thread.clone(), window, cx);
                         })
                     })
diff --git a/crates/sidebar/src/sidebar.rs b/crates/sidebar/src/sidebar.rs
index 32f084a80f329fa01bd79620b26a8a0fca7c8fa6..a658d4dd59c0b2e54c629664c1ae09ab711d3dbd 100644
--- a/crates/sidebar/src/sidebar.rs
+++ b/crates/sidebar/src/sidebar.rs
@@ -3841,7 +3841,14 @@ impl Sidebar {
 
     fn toggle_archive(&mut self, _: &ToggleArchive, window: &mut Window, cx: &mut Context<Self>) {
         match &self.view {
-            SidebarView::ThreadList => self.show_archive(window, cx),
+            SidebarView::ThreadList => {
+                let side = match AgentSettings::get_global(cx).sidebar_side() {
+                    SidebarSide::Left => "left",
+                    SidebarSide::Right => "right",
+                };
+                telemetry::event!("Sidebar Archive Viewed", side = side);
+                self.show_archive(window, cx);
+            }
             SidebarView::Archive(_) => self.show_thread_list(window, cx),
         }
     }
diff --git a/crates/workspace/src/multi_workspace.rs b/crates/workspace/src/multi_workspace.rs
index 5f1f47a4042bae4d8fbd72f04934777bee9c509c..12063d701ac429a31891a82d86044e8531423f66 100644
--- a/crates/workspace/src/multi_workspace.rs
+++ b/crates/workspace/src/multi_workspace.rs
@@ -80,6 +80,11 @@ pub fn sidebar_side_context_menu(
                     IconPosition::Start,
                     None,
                     move |_window, cx| {
+                        let side = match position {
+                            SidebarDockPosition::Left => "left",
+                            SidebarDockPosition::Right => "right",
+                        };
+                        telemetry::event!("Sidebar Side Changed", side = side);
                         settings::update_settings_file(fs.clone(), cx, move |settings, _cx| {
                             settings
                                 .agent