diff --git a/plug-api/types.ts b/plug-api/types.ts
index 6cf8d27..2b2d439 100644
--- a/plug-api/types.ts
+++ b/plug-api/types.ts
@@ -143,5 +143,6 @@ export type LintDiagnostic = {
 
 export type UploadFile = {
   name: string;
+  contentType: string;
   content: Uint8Array;
 }
\ No newline at end of file
diff --git a/plugs/editor/editor.plug.yaml b/plugs/editor/editor.plug.yaml
index 640d782..ddd713f 100644
--- a/plugs/editor/editor.plug.yaml
+++ b/plugs/editor/editor.plug.yaml
@@ -222,3 +222,7 @@ functions:
     command:
       name: "Account: Logout"
 
+  uploadFileCommand:
+    path: ./upload.ts:uploadFile
+    command:
+      name: "Upload: File"
diff --git a/plugs/editor/upload.ts b/plugs/editor/upload.ts
new file mode 100644
index 0000000..1fb4838
--- /dev/null
+++ b/plugs/editor/upload.ts
@@ -0,0 +1,49 @@
+import { editor, space } from "$sb/silverbullet-syscall/mod.ts";
+import { UploadFile } from "$sb/types.ts";
+
+const maximumAttachmentSize = 1024 * 1024 * 10; // 10MB
+
+function folderName(path: string) {
+  return path.split("/").slice(0, -1).join("/");
+}
+
+async function saveFile(file: UploadFile) {
+  if (file.content.length > maximumAttachmentSize) {
+    editor.flashNotification(
+      `Attachment is too large, maximum is ${
+        maximumAttachmentSize / 1024 / 1024
+      }MB`,
+      "error",
+    );
+    return;
+  }
+
+  let prefix = folderName(await editor.getCurrentPage()) + "/";
+  if (prefix === "/") {
+    // root folder case
+    prefix = "";
+  }
+  const suggestedName = prefix + file.name;
+
+  const finalFileName = await editor.prompt(
+    "File name for pasted attachment",
+    suggestedName,
+  );
+  if (!finalFileName) {
+    return;
+  }
+  await space.writeAttachment(
+    finalFileName,
+    file.content,
+  );
+  let attachmentMarkdown = `[${finalFileName}](${encodeURI(finalFileName)})`;
+  if (file.contentType.startsWith("image/")) {
+    attachmentMarkdown = `![](${encodeURI(finalFileName)})`;
+  }
+  editor.insertAtCursor(attachmentMarkdown);
+}
+
+export async function uploadFile() {
+  const uploadFile = await editor.uploadFile();
+  await saveFile(uploadFile);
+}
diff --git a/web/syscalls/editor.ts b/web/syscalls/editor.ts
index ae8c312..6dda6b5 100644
--- a/web/syscalls/editor.ts
+++ b/web/syscalls/editor.ts
@@ -88,6 +88,7 @@ export function editorSyscalls(editor: Client): SysCallMapping {
               if (evt.target?.readyState == FileReader.DONE) {
                 resolve({
                   name: file.name,
+                  contentType: file.type,
                   content: new Uint8Array(await file.arrayBuffer()),
                 });
               }