diff --git a/src/editor/deserialize.ts b/src/editor/deserialize.ts
index b95634ca42..d2ab8da702 100644
--- a/src/editor/deserialize.ts
+++ b/src/editor/deserialize.ts
@@ -242,7 +242,19 @@ function parseHtmlMessage(html: string, partCreator: PartCreator, isQuotedMessag
         }
 
         if (n.nodeType === Node.TEXT_NODE) {
-            newParts.push(...parseAtRoomMentions(n.nodeValue, partCreator));
+            let { nodeValue } = n;
+
+            // Sometimes commonmark adds a newline at the end of the list item text
+            if (n.parentNode.nodeName === "LI") {
+                nodeValue = nodeValue.trimEnd();
+            }
+            newParts.push(...parseAtRoomMentions(nodeValue, partCreator));
+
+            const grandParent = n.parentNode.parentNode;
+            const isTight = n.parentNode.nodeName !== "P" || grandParent?.nodeName !== "LI";
+            if (!isTight) {
+                newParts.push(partCreator.newline());
+            }
         } else if (n.nodeType === Node.ELEMENT_NODE) {
             const parseResult = parseElement(n, partCreator, lastNode, state);
             if (parseResult) {
diff --git a/test/editor/deserialize-test.js b/test/editor/deserialize-test.js
index 2de6375b82..5526ff3df4 100644
--- a/test/editor/deserialize-test.js
+++ b/test/editor/deserialize-test.js
@@ -237,6 +237,18 @@ describe('editor/deserialize', function() {
             expect(parts[3]).toStrictEqual({ type: "newline", text: "\n" });
             expect(parts[4]).toStrictEqual({ type: "plain", text: "3. Finish" });
         });
+        it('non tight lists', () => {
+            const html = "<ol><li><p>Start</p></li><li><p>Continue</p></li><li><p>Finish</p></li></ol>";
+            const parts = normalize(parseEvent(htmlMessage(html), createPartCreator()));
+            expect(parts.length).toBe(8);
+            expect(parts[0]).toStrictEqual({ type: "plain", text: "1. Start" });
+            expect(parts[1]).toStrictEqual({ type: "newline", text: "\n" });
+            expect(parts[2]).toStrictEqual({ type: "newline", text: "\n" });
+            expect(parts[3]).toStrictEqual({ type: "plain", text: "2. Continue" });
+            expect(parts[4]).toStrictEqual({ type: "newline", text: "\n" });
+            expect(parts[5]).toStrictEqual({ type: "newline", text: "\n" });
+            expect(parts[6]).toStrictEqual({ type: "plain", text: "3. Finish" });
+        });
         it('nested unordered lists', () => {
             const html = "<ul><li>Oak<ul><li>Spruce<ul><li>Birch</li></ul></li></ul></li></ul>";
             const parts = normalize(parseEvent(htmlMessage(html), createPartCreator()));
@@ -257,6 +269,16 @@ describe('editor/deserialize', function() {
             expect(parts[3]).toStrictEqual({ type: "newline", text: "\n" });
             expect(parts[4]).toStrictEqual({ type: "plain", text: `${FOUR_SPACES.repeat(2)}1. Birch` });
         });
+        it('nested tight lists', () => {
+            const html = "<ol><li>Oak\n<ol><li>Spruce\n<ol><li>Birch</li></ol></li></ol></li></ol>";
+            const parts = normalize(parseEvent(htmlMessage(html), createPartCreator()));
+            expect(parts.length).toBe(5);
+            expect(parts[0]).toStrictEqual({ type: "plain", text: "1. Oak" });
+            expect(parts[1]).toStrictEqual({ type: "newline", text: "\n" });
+            expect(parts[2]).toStrictEqual({ type: "plain", text: `${FOUR_SPACES}1. Spruce` });
+            expect(parts[3]).toStrictEqual({ type: "newline", text: "\n" });
+            expect(parts[4]).toStrictEqual({ type: "plain", text: `${FOUR_SPACES.repeat(2)}1. Birch` });
+        });
         it('mx-reply is stripped', function() {
             const html = "<mx-reply>foo</mx-reply>bar";
             const parts = normalize(parseEvent(htmlMessage(html), createPartCreator()));