diff --git a/meshchatx/src/frontend/js/LinkUtils.js b/meshchatx/src/frontend/js/LinkUtils.js
index 3ce2572..7836d24 100644
--- a/meshchatx/src/frontend/js/LinkUtils.js
+++ b/meshchatx/src/frontend/js/LinkUtils.js
@@ -6,6 +6,50 @@ function defaultNomadPagePath() {
 }
 
 export default class LinkUtils {
+    static protectAnchors(text) {
+        const anchors = [];
+        const protectedText = text.replace(/<a\b[^>]*>[\s\S]*?<\/a>/gi, (anchor) => {
+            const token = `[[ANCHOR_${anchors.length}]]`;
+            anchors.push(anchor);
+            return token;
+        });
+        return { protectedText, anchors };
+    }
+
+    static restoreAnchors(text, anchors) {
+        return text.replace(/\[\[ANCHOR_(\d+)\]\]/g, (match, idx) => {
+            const i = Number(idx);
+            return Number.isInteger(i) && i >= 0 && i < anchors.length ? anchors[i] : match;
+        });
+    }
+
+    static splitTrailingPunctuation(url) {
+        let core = url;
+        let suffix = "";
+        const alwaysTrim = new Set([".", ",", "!", "?", ":", ";"]);
+        while (core.length > 0) {
+            const ch = core.at(-1);
+            if (alwaysTrim.has(ch)) {
+                suffix = ch + suffix;
+                core = core.slice(0, -1);
+                continue;
+            }
+            if (ch === ")" || ch === "]") {
+                const open = ch === ")" ? "(" : "[";
+                const close = ch;
+                const opens = [...core].filter((c) => c === open).length;
+                const closes = [...core].filter((c) => c === close).length;
+                if (closes > opens) {
+                    suffix = ch + suffix;
+                    core = core.slice(0, -1);
+                    continue;
+                }
+            }
+            break;
+        }
+        return { core, suffix };
+    }
+
     /**
      * Detects and wraps Reticulum (NomadNet and LXMF) links in HTML.
      * Supports nomadnet://<hash>, nomadnet@<hash>, lxmf://<hash>, lxmf@<hash> and bare <hash>
@@ -45,10 +89,13 @@ export default class LinkUtils {
     static renderStandardLinks(text) {
         if (!text) return "";
 
-        // Simple regex for URLs
-        const urlRegex = /(https?:\/\/[^\s<]+)/g;
-        return text.replace(urlRegex, (url) => {
-            return `<a href="${url}" target="_blank" rel="noopener noreferrer" class="text-blue-600 dark:text-blue-400 hover:underline">${url}</a>`;
+        const urlRegex = /(^|[^\w"'=])(https?:\/\/[^\s<]+)/g;
+        return text.replace(urlRegex, (match, prefix, url) => {
+            const { core, suffix } = this.splitTrailingPunctuation(url);
+            if (!core) {
+                return match;
+            }
+            return `${prefix}<a href="${core}" target="_blank" rel="noopener noreferrer" class="text-blue-600 dark:text-blue-400 hover:underline">${core}</a>${suffix}`;
         });
     }
 
@@ -56,8 +103,9 @@ export default class LinkUtils {
      * Applies all link rendering.
      */
     static renderAllLinks(text) {
-        text = this.renderStandardLinks(text);
-        text = this.renderReticulumLinks(text);
-        return text;
+        const { protectedText, anchors } = this.protectAnchors(text);
+        let rendered = this.renderStandardLinks(protectedText);
+        rendered = this.renderReticulumLinks(rendered);
+        return this.restoreAnchors(rendered, anchors);
     }
 }
diff --git a/tests/frontend/LinkUtils.test.js b/tests/frontend/LinkUtils.test.js
index 07db1c8..75a2383 100644
--- a/tests/frontend/LinkUtils.test.js
+++ b/tests/frontend/LinkUtils.test.js
@@ -58,6 +58,27 @@ describe("LinkUtils.js", () => {
             const result = LinkUtils.renderStandardLinks(text);
             expect(result).toContain('<a href="https://example.com/path?query=1"');
         });
+
+        it("trims trailing punctuation from detected urls", () => {
+            const result = LinkUtils.renderStandardLinks("visit https://example.com/path?x=1, now");
+            expect(result).toContain('href="https://example.com/path?x=1"');
+            expect(result).toContain("</a>, now");
+        });
+
+        it("keeps balanced parenthesis in url but trims unmatched trailing one", () => {
+            const withBalanced = LinkUtils.renderStandardLinks("see https://example.com/path_(v1)");
+            expect(withBalanced).toContain('href="https://example.com/path_(v1)"');
+
+            const withTrailing = LinkUtils.renderStandardLinks("see (https://example.com/path_(v1))");
+            expect(withTrailing).toContain('href="https://example.com/path_(v1)"');
+            expect(withTrailing).toContain("</a>)");
+        });
+
+        it("keeps escaped entity query content in href", () => {
+            const text = "visit https://example.com/search?q=a&amp;lang=en";
+            const result = LinkUtils.renderStandardLinks(text);
+            expect(result).toContain('href="https://example.com/search?q=a&amp;lang=en"');
+        });
     });
 
     describe("renderAllLinks", () => {
@@ -77,6 +98,19 @@ describe("LinkUtils.js", () => {
             expect(result).toContain("Just some words.");
             expect(result).not.toContain("<a ");
         });
+
+        it("does not double-wrap urls inside existing anchors", () => {
+            const original = 'already linked <a href="https://example.com">https://example.com</a>';
+            const result = LinkUtils.renderAllLinks(original);
+            expect(result).toBe(original);
+            expect((result.match(/<a /g) || []).length).toBe(1);
+        });
+
+        it("keeps reticulum path underscores", () => {
+            const text = "1dfeb0d794963579bd21ac8f153c77a4:/page/meshchatx_on_pi.mu";
+            const result = LinkUtils.renderAllLinks(text);
+            expect(result).toContain('data-nomadnet-url="1dfeb0d794963579bd21ac8f153c77a4:/page/meshchatx_on_pi.mu"');
+        });
     });
 
     describe("risky: no script or data URLs in href", () => {
diff --git a/tests/frontend/MarkdownRenderer.test.js b/tests/frontend/MarkdownRenderer.test.js
index b36cb04..038212b 100644
--- a/tests/frontend/MarkdownRenderer.test.js
+++ b/tests/frontend/MarkdownRenderer.test.js
@@ -88,6 +88,58 @@ describe("MarkdownRenderer.js", () => {
             expect(result).not.toContain("<em>on</em>");
             expect(result).not.toContain("<em>raspberry</em>");
         });
+
+        it("renders multiple urls in one line without corruption", () => {
+            const a = "https://example.com/docs/meshchatx_on_pi.md";
+            const b = "https://example.com/plain";
+            const result = MarkdownRenderer.render(`links: ${a} and ${b}`);
+            expect(result).toContain(`href="${a}"`);
+            expect(result).toContain(`href="${b}"`);
+            expect((result.match(/<a href=/g) || []).length).toBe(2);
+        });
+
+        it("trims trailing punctuation around links while keeping display punctuation", () => {
+            const result = MarkdownRenderer.render("Check (https://example.com/path_(v1)), and continue.");
+            expect(result).toContain('href="https://example.com/path_(v1)"');
+            expect(result).toContain("</a>), and continue.");
+        });
+
+        it("supports encoded chars and balanced parentheses in link path", () => {
+            const url = "https://example.com/docs/file%5Fname_(v1).md";
+            const result = MarkdownRenderer.render(`open ${url}`);
+            expect(result).toContain(`href="${url}"`);
+        });
+
+        it("keeps escaped entities in query string links", () => {
+            const url = "https://example.com/search?q=a&amp;lang=en";
+            const result = MarkdownRenderer.render(`lookup ${url}`);
+            expect(result).toContain('href="https://example.com/search?q=a&amp;amp;lang=en"');
+            expect(result).toContain("https://example.com/search?q=a&amp;amp;lang=en");
+        });
+
+        it("handles links at line boundaries with newline conversion", () => {
+            const url = "https://example.com/meshchatx_on_pi.md";
+            const result = MarkdownRenderer.render(`${url}\nnext line`);
+            expect(result).toContain(`href="${url}"`);
+            expect(result).toContain("<br>next line");
+        });
+
+        it("mixes underscore markdown with underscore urls safely", () => {
+            const url = "https://example.com/meshchatx_on_raspberry_pi.md";
+            const result = MarkdownRenderer.render(`_label_ ${url} _tail_`);
+            expect(result).toContain("<em>label</em>");
+            expect(result).toContain("<em>tail</em>");
+            expect(result).toContain(`href="${url}"`);
+            expect(result).not.toContain("<em>on</em>");
+        });
+
+        it("escapes pre-rendered html input safely instead of nesting raw anchors", () => {
+            const preRendered = '<p><a href="https://example.com/path_(v1)">https://example.com/path_(v1)</a></p>';
+            const result = MarkdownRenderer.render(preRendered);
+            expect(result).toContain("&lt;p&gt;");
+            expect(result).toContain("&lt;a href=&quot;");
+            expect(result).not.toContain("<script");
+        });
     });
 
     describe("security: XSS prevention", () => {
@@ -255,6 +307,35 @@ describe("MarkdownRenderer.js", () => {
                 expect(() => MarkdownRenderer.render(text)).not.toThrow();
             });
         });
+
+        it("underscore-heavy fuzz input does not create unbalanced emphasis tags", () => {
+            const randomUnderscoreText = () => {
+                const parts = [
+                    "_",
+                    "__",
+                    "___",
+                    "snake_case",
+                    "meshchatx_on_pi",
+                    " ",
+                    "text",
+                    "https://example.com/meshchatx_on_pi.md",
+                ];
+                let out = "";
+                for (let i = 0; i < 200; i++) {
+                    out += parts[Math.floor(Math.random() * parts.length)];
+                }
+                return out;
+            };
+            for (let i = 0; i < 50; i++) {
+                const rendered = MarkdownRenderer.render(randomUnderscoreText());
+                const opensEm = (rendered.match(/<em>/g) || []).length;
+                const closesEm = (rendered.match(/<\/em>/g) || []).length;
+                const opensStrong = (rendered.match(/<strong>/g) || []).length;
+                const closesStrong = (rendered.match(/<\/strong>/g) || []).length;
+                expect(opensEm).toBe(closesEm);
+                expect(opensStrong).toBe(closesStrong);
+            }
+        });
     });
 
     describe("isSingleEmojiMessage", () => {
@@ -397,5 +478,29 @@ describe("MarkdownRenderer.js", () => {
             const r = MarkdownRenderer.render(msg);
             expect(typeof r).toBe("string");
         });
+
+        it("renders a real-world mixed message body safely", () => {
+            const msg = [
+                "# Deploy notes",
+                "",
+                "Read https://git.quad4.io/RNS-Things/MeshChatX/src/branch/dev/docs/meshchatx_on_raspberry_pi.md, then ping",
+                "nomadnet://1dfeb0d794963579bd21ac8f153c77a4:/page/meshchatx_on_pi.mu",
+                "",
+                "`inline_code` and _italic_ and snake_case stay sane.",
+                "",
+                "```txt",
+                "https://example.com/not_linked_inside_code",
+                "```",
+            ].join("\n");
+            const result = MarkdownRenderer.render(msg);
+            expect(result).toContain("<h1");
+            expect(result).toContain(
+                'href="https://git.quad4.io/RNS-Things/MeshChatX/src/branch/dev/docs/meshchatx_on_raspberry_pi.md"'
+            );
+            expect(result).toContain('data-nomadnet-url="1dfeb0d794963579bd21ac8f153c77a4:/page/meshchatx_on_pi.mu"');
+            expect(result).toContain("<code");
+            expect(result).toContain("<pre");
+            expect(result).not.toContain("<em>case</em>");
+        });
     });
 });