diff --git a/app/editor/extensions/ClipboardTextSerializer.ts b/app/editor/extensions/ClipboardTextSerializer.ts
index b5a05a7f70..c1146c87fa 100644
--- a/app/editor/extensions/ClipboardTextSerializer.ts
+++ b/app/editor/extensions/ClipboardTextSerializer.ts
@@ -61,7 +61,7 @@ export default class ClipboardTextSerializer extends Extension {
                   .map((node) => ProsemirrorHelper.toPlainText(node))
                   .join("\n")
               : mdSerializer.serialize(slice.content, {
-                  softBreak: true,
+                  commonMark: true,
                 });
           },
         },
diff --git a/app/models/helpers/ProsemirrorHelper.ts b/app/models/helpers/ProsemirrorHelper.ts
index c48534e231..8e268fd051 100644
--- a/app/models/helpers/ProsemirrorHelper.ts
+++ b/app/models/helpers/ProsemirrorHelper.ts
@@ -29,7 +29,7 @@ export class ProsemirrorHelper {
     );
 
     const markdown = serializer.serialize(doc, {
-      softBreak: true,
+      commonMark: true,
     });
     return markdown;
   };
diff --git a/shared/editor/lib/markdown/serializer.ts b/shared/editor/lib/markdown/serializer.ts
index 85a1d82ad3..5eec8aba7a 100644
--- a/shared/editor/lib/markdown/serializer.ts
+++ b/shared/editor/lib/markdown/serializer.ts
@@ -3,7 +3,18 @@
 // https://raw.githubusercontent.com/ProseMirror/prosemirror-markdown/master/src/to_markdown.js
 // forked for table support
 
-type Options = { tightLists?: boolean; softBreak?: boolean };
+/** Options that control how a ProseMirror document is serialized to Markdown. */
+type Options = {
+  /** Whether list items are rendered without blank lines between them. */
+  tightLists?: boolean;
+  /**
+   * Whether to emit portable, standard CommonMark intended to leave Outline,
+   * such as when copying to the clipboard or exporting. When false the
+   * serializer uses Outline's internal escaped representation, which round-trips
+   * losslessly through its own parser but is not standard Markdown.
+   */
+  commonMark?: boolean;
+};
 
 // ::- A specification for serializing a ProseMirror document as
 // Markdown/CommonMark text.
diff --git a/shared/editor/nodes/HardBreak.ts b/shared/editor/nodes/HardBreak.ts
index 2ce830c0c1..34292759e1 100644
--- a/shared/editor/nodes/HardBreak.ts
+++ b/shared/editor/nodes/HardBreak.ts
@@ -55,8 +55,10 @@ export default class HardBreak extends Node {
   }
 
   toMarkdown(state: MarkdownSerializerState) {
+    // Two trailing spaces is a CommonMark hard break that survives a
+    // copy/export round-trip, unlike a bare newline.
     state.write(
-      state.inTable ? "<br>" : state.options.softBreak ? "\n" : "\\n"
+      state.inTable ? "<br>" : state.options.commonMark ? "  \n" : "\\n"
     );
   }
 
diff --git a/shared/editor/nodes/Paragraph.ts b/shared/editor/nodes/Paragraph.ts
index d458cea4ee..6b91cee92d 100644
--- a/shared/editor/nodes/Paragraph.ts
+++ b/shared/editor/nodes/Paragraph.ts
@@ -58,7 +58,7 @@ export default class Paragraph extends Node {
       node.childCount === 0 &&
       !state.inTable
     ) {
-      state.write(state.options.softBreak ? "\n" : "\\\n");
+      state.write(state.options.commonMark ? "\n" : "\\\n");
     } else {
       state.renderInline(node);
       state.closeBlock(node);
diff --git a/server/editor/checkboxes.test.ts b/shared/editor/rules/checkboxes.test.ts
similarity index 90%
rename from server/editor/checkboxes.test.ts
rename to shared/editor/rules/checkboxes.test.ts
index 3a31ff25e2..c9db14d8da 100644
--- a/server/editor/checkboxes.test.ts
+++ b/shared/editor/rules/checkboxes.test.ts
@@ -1,4 +1,10 @@
-import { parser, serializer } from "@server/editor";
+import { extensionManager, schema } from "../../test/editor";
+
+const serializer = extensionManager.serializer();
+const parser = extensionManager.parser({
+  schema,
+  plugins: extensionManager.rulePlugins,
+});
 
 interface ProsemirrorNode {
   type: string;
diff --git a/shared/editor/rules/hardbreaks.test.ts b/shared/editor/rules/hardbreaks.test.ts
new file mode 100644
index 0000000000..0c4984c6de
--- /dev/null
+++ b/shared/editor/rules/hardbreaks.test.ts
@@ -0,0 +1,88 @@
+import { extensionManager, schema } from "../../test/editor";
+
+const serializer = extensionManager.serializer();
+const parser = extensionManager.parser({
+  schema,
+  plugins: extensionManager.rulePlugins,
+});
+
+const docWithHardBreak = schema.nodeFromJSON({
+  type: "doc",
+  content: [
+    {
+      type: "paragraph",
+      content: [
+        { type: "text", text: "Line one" },
+        { type: "br" },
+        { type: "text", text: "Line two" },
+      ],
+    },
+  ],
+});
+
+it("parses two trailing spaces as a hard break", () => {
+  const ast = parser.parse("Line one  \nLine two");
+
+  expect(ast?.toJSON()).toEqual(docWithHardBreak.toJSON());
+});
+
+it("parses a backslash line ending as a hard break", () => {
+  const ast = parser.parse("Line one\\\nLine two");
+
+  expect(ast?.toJSON()).toEqual(docWithHardBreak.toJSON());
+});
+
+it("serializes hard breaks as a CommonMark break when commonMark is set", () => {
+  // The commonMark option is used when copying to the clipboard and exporting
+  // documents – two trailing spaces are a standard Markdown hard break that
+  // renders in external viewers and parses back into a `br`, unlike a bare
+  // newline.
+  expect(serializer.serialize(docWithHardBreak, { commonMark: true })).toBe(
+    "Line one  \nLine two"
+  );
+});
+
+it("round-trips hard breaks through the copy/export serializer", () => {
+  let node = docWithHardBreak;
+
+  for (let i = 0; i < 3; i++) {
+    const markdown = serializer.serialize(node, { commonMark: true });
+    node = parser.parse(markdown)!;
+    expect(node.toJSON()).toEqual(docWithHardBreak.toJSON());
+  }
+});
+
+it("serializes hard breaks inside tables as a literal break tag", () => {
+  const docWithTable = schema.nodeFromJSON({
+    type: "doc",
+    content: [
+      {
+        type: "table",
+        content: [
+          {
+            type: "tr",
+            content: [
+              {
+                type: "td",
+                content: [
+                  {
+                    type: "paragraph",
+                    content: [
+                      { type: "text", text: "Line one" },
+                      { type: "br" },
+                      { type: "text", text: "Line two" },
+                    ],
+                  },
+                ],
+              },
+            ],
+          },
+        ],
+      },
+    ],
+  });
+
+  expect(serializer.serialize(docWithTable, { commonMark: true })).toContain(
+    "Line one<br>Line two"
+  );
+});