diff --git a/helix-term/src/handlers/auto_save.rs b/helix-term/src/handlers/auto_save.rs
index d3f7f6fc124a..4e154df808a7 100644
--- a/helix-term/src/handlers/auto_save.rs
+++ b/helix-term/src/handlers/auto_save.rs
@@ -1,39 +1,82 @@
-use std::time::Duration;
+use std::{
+    sync::{
+        atomic::{self, AtomicBool},
+        Arc,
+    },
+    time::Duration,
+};
 
 use anyhow::Ok;
 use arc_swap::access::Access;
 
 use helix_event::{register_hook, send_blocking};
-use helix_view::{events::DocumentDidChange, handlers::Handlers, Editor};
+use helix_view::{
+    document::Mode,
+    events::DocumentDidChange,
+    handlers::{AutoSaveEvent, Handlers},
+    Editor,
+};
 use tokio::time::Instant;
 
 use crate::{
     commands, compositor,
+    events::OnModeSwitch,
     job::{self, Jobs},
 };
 
 #[derive(Debug)]
-pub(super) struct AutoSaveHandler;
+pub(super) struct AutoSaveHandler {
+    save_pending: Arc<AtomicBool>,
+}
 
 impl AutoSaveHandler {
     pub fn new() -> AutoSaveHandler {
-        AutoSaveHandler
+        AutoSaveHandler {
+            save_pending: Default::default(),
+        }
     }
 }
 
 impl helix_event::AsyncHook for AutoSaveHandler {
-    type Event = u64;
+    type Event = AutoSaveEvent;
 
     fn handle_event(
         &mut self,
-        timeout: Self::Event,
-        _: Option<tokio::time::Instant>,
+        event: Self::Event,
+        existing_debounce: Option<tokio::time::Instant>,
     ) -> Option<Instant> {
-        Some(Instant::now() + Duration::from_millis(timeout))
+        match event {
+            Self::Event::DocumentChanged { save_after } => {
+                Some(Instant::now() + Duration::from_millis(save_after))
+            }
+            Self::Event::LeftInsertMode => {
+                if existing_debounce.is_some() {
+                    // If the change happened more recently than the debounce, let the
+                    // debounce run down before saving.
+                    existing_debounce
+                } else {
+                    // Otherwise if there is a save pending, save immediately.
+                    if self.save_pending.load(atomic::Ordering::Relaxed) {
+                        self.finish_debounce();
+                    }
+                    None
+                }
+            }
+        }
     }
 
     fn finish_debounce(&mut self) {
-        job::dispatch_blocking(move |editor, _| request_auto_save(editor))
+        let save_pending = self.save_pending.clone();
+        job::dispatch_blocking(move |editor, _| {
+            if editor.mode() == Mode::Insert {
+                // Avoid saving while in insert mode since this mixes up
+                // the modification indicator and prevents future saves.
+                save_pending.store(true, atomic::Ordering::Relaxed);
+            } else {
+                request_auto_save(editor);
+                save_pending.store(false, atomic::Ordering::Relaxed);
+            }
+        })
     }
 }
 
@@ -54,7 +97,20 @@ pub(super) fn register_hooks(handlers: &Handlers) {
     register_hook!(move |event: &mut DocumentDidChange<'_>| {
         let config = event.doc.config.load();
         if config.auto_save.after_delay.enable {
-            send_blocking(&tx, config.auto_save.after_delay.timeout);
+            send_blocking(
+                &tx,
+                AutoSaveEvent::DocumentChanged {
+                    save_after: config.auto_save.after_delay.timeout,
+                },
+            );
+        }
+        Ok(())
+    });
+
+    let tx = handlers.auto_save.clone();
+    register_hook!(move |event: &mut OnModeSwitch<'_, '_>| {
+        if event.old_mode == Mode::Insert {
+            send_blocking(&tx, AutoSaveEvent::LeftInsertMode)
         }
         Ok(())
     });
diff --git a/helix-view/src/handlers.rs b/helix-view/src/handlers.rs
index 352abb881306..e2848f26487d 100644
--- a/helix-view/src/handlers.rs
+++ b/helix-view/src/handlers.rs
@@ -7,11 +7,17 @@ use crate::{DocumentId, Editor, ViewId};
 pub mod dap;
 pub mod lsp;
 
+#[derive(Debug)]
+pub enum AutoSaveEvent {
+    DocumentChanged { save_after: u64 },
+    LeftInsertMode,
+}
+
 pub struct Handlers {
     // only public because most of the actual implementation is in helix-term right now :/
     pub completions: Sender<lsp::CompletionEvent>,
     pub signature_hints: Sender<lsp::SignatureHelpEvent>,
-    pub auto_save: Sender<u64>,
+    pub auto_save: Sender<AutoSaveEvent>,
 }
 
 impl Handlers {