diff --git a/packages/tree-view/lib/tree-view.js b/packages/tree-view/lib/tree-view.js
index c9d128f1b4..b93825a36e 100644
--- a/packages/tree-view/lib/tree-view.js
+++ b/packages/tree-view/lib/tree-view.js
@@ -929,7 +929,7 @@ class TreeView {
 
           this.emitter.emit('will-delete-entry', meta);
 
-          let promise = shell.trashItem(selectedPath).then(() => {
+          let promise = atom.trashItem(selectedPath).then(() => {
             this.emitter.emit('entry-deleted', meta);
           }).catch(() => {
             this.emitter.emit('delete-entry-failed', meta);
diff --git a/src/application-delegate.js b/src/application-delegate.js
index 0c68c688f8..bf90d552f6 100644
--- a/src/application-delegate.js
+++ b/src/application-delegate.js
@@ -34,7 +34,7 @@ module.exports = class ApplicationDelegate {
 
   pickFolder(callback) {
     const responseChannel = 'atom-pick-folder-response';
-    ipcRenderer.on(responseChannel, function(event, path) {
+    ipcRenderer.on(responseChannel, function (event, path) {
       ipcRenderer.removeAllListeners(responseChannel);
       return callback(path);
     });
@@ -132,6 +132,20 @@ module.exports = class ApplicationDelegate {
     return ipcHelpers.on(ipcRenderer, 'did-leave-full-screen', callback);
   }
 
+  trashItem(filePath) {
+    // A simple wrapper around `shell.trashItem`, which currently can only be
+    // called from the main process on Windows.
+    return ipcRenderer.invoke('trashItem', filePath).then(({ outcome, error, result }) => {
+      if (outcome === 'success') {
+        // `result` is undefined, but we might as well guard against an
+        // Electron API change in the future.
+        return result;
+      } else if (outcome === 'failure') {
+        return Promise.reject(error);
+      }
+    });
+  }
+
   async openWindowDevTools() {
     // Defer DevTools interaction to the next tick, because using them during
     // event handling causes some wrong input events to be triggered on
diff --git a/src/atom-environment.js b/src/atom-environment.js
index a507739133..a8829868fe 100644
--- a/src/atom-environment.js
+++ b/src/atom-environment.js
@@ -776,6 +776,16 @@ class AtomEnvironment {
     return this.setFullScreen(!this.isFullScreen());
   }
 
+  // A proxy to `shell.trashItem` — which ought to work in the renderer, but
+  // suffers from a bug on Windows. We work around it by delegating to the main
+  // process.
+  //
+  // Undocumented for now, but may eventually be an official part of the API
+  // for when community packages need to delete files.
+  trashItem(filePath) {
+    return this.applicationDelegate.trashItem(filePath);
+  }
+
   // Restore the window to its previous dimensions and show it.
   //
   // Restores the full screen and maximized state after the window has resized to
diff --git a/src/main-process/atom-application.js b/src/main-process/atom-application.js
index fd6ae5006b..0946ac8a41 100644
--- a/src/main-process/atom-application.js
+++ b/src/main-process/atom-application.js
@@ -135,6 +135,30 @@ ipcMain.handle('isDefaultProtocolClient', (_, { protocol, path, args }) => {
 ipcMain.handle('setAsDefaultProtocolClient', (_, { protocol, path, args }) => {
   return app.setAsDefaultProtocolClient(protocol, path, args);
 });
+
+// Handle file deletion requests.
+//
+// Works around https://github.com/electron/electron/issues/29598, which seems
+// to be the cause of failed deletion attempts on Windows.
+ipcMain.handle('trashItem', async (_, filePath) => {
+  // We can't toss a promise over the wall, so we'll `await` it on our side and
+  // report the progress back to the renderer.
+  //
+  // If we return an `Error` object from this handler in the case of error,
+  // `ipcRenderer.invoke` will detect it and wrap it with its own explanation.
+  // We want to preserve the original error and hide the implementation
+  // details, so we instead return an object with an explicit `outcome`
+  // property to avoid this behavior.
+  try {
+    // `shell.trashItem` resolves with an empty value on success…
+    let result = await shell.trashItem(filePath);
+    return { outcome: 'success', result };
+  } catch (error) {
+    // …and rejects on failure.
+    return { outcome: 'failure', error }
+  }
+});
+
 // The application's singleton class.
 //
 // It's the entry point into the Pulsar application and maintains the global state