diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 5fc2c513..a3f206ee 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -10,9 +10,9 @@ jobs:
     lint:
         runs-on: ubuntu-latest
         steps:
-            - uses: actions/checkout@v3
+            - uses: actions/checkout@v4
             - name: Setup Node.js environment
-              uses: actions/setup-node@v3
+              uses: actions/setup-node@v4
               with:
                   node-version: lts/*
                   cache: "npm"
@@ -25,10 +25,10 @@ jobs:
     unit-test:
         runs-on: ubuntu-latest
         steps:
-            - uses: actions/checkout@v3
+            - uses: actions/checkout@v4
 
             - name: Setup Node.js environment
-              uses: actions/setup-node@v3
+              uses: actions/setup-node@v4
               with:
                   node-version: lts/*
                   cache: "npm"
@@ -41,10 +41,10 @@ jobs:
     e2e-test:
         runs-on: ubuntu-latest
         steps:
-            - uses: actions/checkout@v3
+            - uses: actions/checkout@v4
 
             - name: Setup Node.js environment
-              uses: actions/setup-node@v3
+              uses: actions/setup-node@v4
               with:
                   node-version: lts/*
                   cache: "npm"
@@ -58,7 +58,7 @@ jobs:
             - name: Run E2E tests
               run: npm run test:e2e
 
-            - uses: actions/upload-artifact@v3
+            - uses: actions/upload-artifact@v4
               if: failure()
               with:
                   name: playwright-test-results
diff --git a/src/shared/markdown-serializer.ts b/src/shared/markdown-serializer.ts
index 1c42cff3..ccf2cab6 100644
--- a/src/shared/markdown-serializer.ts
+++ b/src/shared/markdown-serializer.ts
@@ -330,10 +330,13 @@ const defaultMarkdownSerializerNodes: MarkdownSerializerNodes = {
         ) {
             text = linkMark.attrs.href as string;
         } else {
-            // eslint-disable-next-line @typescript-eslint/ban-ts-comment
-            // @ts-expect-error
-            // eslint-disable-next-line @typescript-eslint/no-unsafe-assignment, @typescript-eslint/no-unsafe-call
-            const startOfLine: boolean = state.atBlank() || state.closed;
+            /* eslint-disable @typescript-eslint/ban-ts-comment, @typescript-eslint/no-unsafe-assignment */
+            const startOfLine: boolean =
+                // @ts-expect-error
+                // eslint-disable-next-line
+                state.atBlank() || state.atBlockStart || state.closed;
+            /* eslint-enable @typescript-eslint/ban-ts-comment, @typescript-eslint/no-unsafe-assignment */
+
             // escape the text using the built in escape code
             let escapedText = state.esc(node.text, startOfLine);
 
diff --git a/test/shared/roundtrip.e2e.test.ts b/test/shared/roundtrip.e2e.test.ts
new file mode 100644
index 00000000..398f9d44
--- /dev/null
+++ b/test/shared/roundtrip.e2e.test.ts
@@ -0,0 +1,56 @@
+import { test, expect, Page } from "@playwright/test";
+import {
+    switchMode,
+    clearEditor,
+    editorSelector,
+    enterTextAsMarkdown,
+} from "../e2e-helpers";
+
+test.describe.serial("roundtrip tests", () => {
+    let page: Page;
+    test.beforeAll(async ({ browser }) => {
+        page = await browser.newPage();
+        await page.goto("/empty.html");
+        await switchMode(page, "markdown");
+    });
+
+    test.afterAll(async () => {
+        await page.close();
+    });
+
+    for (const [markdown] of [
+        //Basic commonmark
+        ["plain"],
+        ["*italic*"],
+        ["_italic_"],
+        ["**bold**"],
+        ["__bold__"],
+        ["# H1"],
+        ["## H2"],
+        ["[link](http://www.example.com)"],
+        ["![Image](http://www.example.com/pretty.png)"],
+        ["> blockquote"],
+        ["* List Item"],
+        ["- List Item"],
+        ["1. List Item"],
+        ["2) List Item"],
+        ["lol\n\n---\n\nlmao"],
+        ["lol\n\n***\n\nlmao"],
+        ["`code`"],
+        //TODO: Codeblock does weird things roundtripping: Adds an extra space
+        //['```javascript\ncodeblock\n```' ],
+
+        //Escape character
+        [String.raw`\# not a header`],
+        [String.raw`- \# list item (not header)`],
+    ] as const) {
+        test(`should make markdown -> richtext -> markdown round trip '${JSON.stringify(markdown)}'`, async () => {
+            await clearEditor(page);
+            await enterTextAsMarkdown(page, markdown);
+            await switchMode(page, "markdown");
+
+            const text = await page.innerText(editorSelector);
+            expect(text).toBe(markdown);
+        });
+    }
+});