diff --git a/server/utils/turndown/emptyParagraph.ts b/server/utils/turndown/emptyParagraph.ts
index 1b2017876..449f64814 100644
--- a/server/utils/turndown/emptyParagraph.ts
+++ b/server/utils/turndown/emptyParagraph.ts
@@ -11,6 +11,7 @@ export default function emptyParagraphs(turndownService: TurndownService) {
       return (
         node.nodeName === "P" &&
         node.children.length === 1 &&
+        node.textContent?.trim() === "" &&
         node.children[0].nodeName === "BR"
       );
     },
diff --git a/server/utils/turndown/images.ts b/server/utils/turndown/images.ts
index 3676d03d7..b59b99eed 100644
--- a/server/utils/turndown/images.ts
+++ b/server/utils/turndown/images.ts
@@ -7,20 +7,44 @@ import TurndownService from "turndown";
  */
 export default function images(turndownService: TurndownService) {
   turndownService.addRule("image", {
-    filter: "img",
+    filter(node) {
+      return node.nodeName === "IMG" && !node?.className.includes("emoticon");
+    },
     replacement(content, node) {
       if (!("className" in node)) {
         return content;
       }
       const alt = cleanAttribute(node.getAttribute("alt") || "");
-      const src = (node.getAttribute("src") || "").replace(/\n+/g, "");
+      const src = cleanAttribute(node.getAttribute("src") || "");
       const title = cleanAttribute(node.getAttribute("title") || "");
-      const titlePart = title ? ' "' + title + '"' : "";
-      return src ? "![" + alt + "]" + "(" + src + titlePart + ")" : "";
+
+      // Remove icons in issue keys as they will not resolve correctly and mess
+      // up the layout.
+      if (
+        node.className === "icon" &&
+        node.parentElement?.className.includes("jira-issue-key")
+      ) {
+        return "";
+      }
+
+      // Respect embedded Confluence image size
+      let size;
+      const naturalWidth = node.getAttribute("data-width");
+      const naturalHeight = node.getAttribute("data-height");
+      const width = node.getAttribute("width");
+
+      if (naturalWidth && naturalHeight && width) {
+        const ratio = parseInt(naturalWidth) / parseInt(width);
+        size = ` =${width}x${parseInt(naturalHeight) / ratio}`;
+      }
+
+      const titlePart = title || size ? ` "${title}${size}"` : "";
+
+      return src ? `![${alt}](${src}${titlePart})` : "";
     },
   });
 }
 
 function cleanAttribute(attribute: string) {
-  return attribute ? attribute.replace(/(\n+\s*)+/g, "\n") : "";
+  return (attribute ? attribute.replace(/\n+/g, "") : "").trim();
 }
diff --git a/server/utils/turndown/index.ts b/server/utils/turndown/index.ts
index 4d3596368..120024c6f 100644
--- a/server/utils/turndown/index.ts
+++ b/server/utils/turndown/index.ts
@@ -2,9 +2,10 @@ import { gfm } from "@joplin/turndown-plugin-gfm";
 import TurndownService from "turndown";
 import breaks from "./breaks";
 import emptyLists from "./emptyLists";
-import emptyParagraphs from "./emptyParagraph";
+import emptyParagraph from "./emptyParagraph";
 import frames from "./frames";
 import images from "./images";
+import sanitizeLists from "./sanitizeLists";
 import sanitizeTables from "./sanitizeTables";
 import underlines from "./underlines";
 
@@ -18,17 +19,14 @@ const service = new TurndownService({
   bulletListMarker: "-",
   headingStyle: "atx",
   codeBlockStyle: "fenced",
-  blankReplacement: (content, node) => {
-    if (node.nodeName === "P") {
-      return "\n\n\\\n";
-    }
-    return "";
-  },
+  blankReplacement: (content, node) =>
+    node.nodeName === "P" ? "\n\n\\\n" : "",
 })
   .remove(["script", "style", "title", "head"])
   .use(gfm)
-  .use(emptyParagraphs)
+  .use(emptyParagraph)
   .use(sanitizeTables)
+  .use(sanitizeLists)
   .use(underlines)
   .use(frames)
   .use(images)
diff --git a/server/utils/turndown/sanitizeLists.ts b/server/utils/turndown/sanitizeLists.ts
new file mode 100644
index 000000000..d9dcc43f8
--- /dev/null
+++ b/server/utils/turndown/sanitizeLists.ts
@@ -0,0 +1,51 @@
+import TurndownService from "turndown";
+
+/**
+ * A turndown plugin for removing incompatible nodes from lists.
+ *
+ * @param turndownService The TurndownService instance.
+ */
+export default function sanitizeLists(turndownService: TurndownService) {
+  function inHtmlContext(node: HTMLElement, selector: string) {
+    let currentNode = node;
+    // start at the closest element
+    while (currentNode !== null && currentNode.nodeType !== 1) {
+      currentNode = (currentNode.parentElement ||
+        currentNode.parentNode) as HTMLElement;
+    }
+    return (
+      currentNode !== null &&
+      currentNode.nodeType === 1 &&
+      currentNode.closest(selector) !== null
+    );
+  }
+
+  turndownService.addRule("headingsInLists", {
+    filter(node) {
+      return (
+        ["H1", "H2", "H3", "H4", "H5", "H6"].includes(node.nodeName) &&
+        inHtmlContext(node, "LI")
+      );
+    },
+    replacement(content, node, options) {
+      if (!content.trim()) {
+        return "";
+      }
+      return options.strongDelimiter + content + options.strongDelimiter;
+    },
+  });
+
+  turndownService.addRule("strongInHeadings", {
+    filter(node) {
+      return (
+        (node.nodeName === "STRONG" || node.nodeName === "B") &&
+        ["H1", "H2", "H3", "H4", "H5", "H6"].some((tag) =>
+          inHtmlContext(node, tag)
+        )
+      );
+    },
+    replacement(content) {
+      return content;
+    },
+  });
+}