diff --git a/src/components/AdvancedEventLab/AdvancedEventLabMarkupToolbar.tsx b/src/components/AdvancedEventLab/AdvancedEventLabMarkupToolbar.tsx
index 7a962f3f..a74b40d1 100644
--- a/src/components/AdvancedEventLab/AdvancedEventLabMarkupToolbar.tsx
+++ b/src/components/AdvancedEventLab/AdvancedEventLabMarkupToolbar.tsx
@@ -176,8 +176,31 @@ export function AdvancedEventLabMarkupToolbar({
               )
             })}
             <DropdownMenuSeparator />
-            <DropdownMenuItem onClick={() => run((v) => labInsertRaw(v, sliceRef, '\n---\n'))}>
-              {t('Advanced lab tb horizontalRule')}
+            <DropdownMenuItem
+              onClick={() =>
+                run((v) =>
+                  labInsertRaw(
+                    v,
+                    sliceRef,
+                    `\n${t('Advanced lab tb heading placeholder')}\n===\n`
+                  )
+                )
+              }
+            >
+              {t('Advanced lab tb setextH1')}
+            </DropdownMenuItem>
+            <DropdownMenuItem
+              onClick={() =>
+                run((v) =>
+                  labInsertRaw(
+                    v,
+                    sliceRef,
+                    `\n${t('Advanced lab tb heading placeholder')}\n---\n`
+                  )
+                )
+              }
+            >
+              {t('Advanced lab tb setextH2')}
             </DropdownMenuItem>
           </DropdownMenuContent>
         </DropdownMenu>
@@ -197,6 +220,12 @@ export function AdvancedEventLabMarkupToolbar({
             <DropdownMenuItem onClick={() => run((v) => labWrapOrSnippet(v, sliceRef, '*', 'italic'))}>
               {t('Advanced lab tb italic')}
             </DropdownMenuItem>
+            <DropdownMenuItem onClick={() => run((v) => labWrapOrSnippet(v, sliceRef, '__', 'bold'))}>
+              {t('Advanced lab tb boldUnderscore')}
+            </DropdownMenuItem>
+            <DropdownMenuItem onClick={() => run((v) => labWrapOrSnippet(v, sliceRef, '_', 'italic'))}>
+              {t('Advanced lab tb italicUnderscore')}
+            </DropdownMenuItem>
             <DropdownMenuItem onClick={() => run((v) => labWrapOrSnippet(v, sliceRef, '~~', 'strikethrough'))}>
               {t('Advanced lab tb strike')}
             </DropdownMenuItem>
@@ -224,6 +253,44 @@ export function AdvancedEventLabMarkupToolbar({
               <ImageIcon className="h-3.5 w-3.5 mr-2 inline" />
               {t('Advanced lab tb image')}
             </DropdownMenuItem>
+            <DropdownMenuSeparator />
+            <DropdownMenuItem
+              onClick={() =>
+                run((v) =>
+                  labInsertSnippet(
+                    v,
+                    sliceRef,
+                    '[',
+                    'link text',
+                    '](https://example.com "Link title")'
+                  )
+                )
+              }
+            >
+              <Link2 className="h-3.5 w-3.5 mr-2 inline" />
+              {t('Advanced lab tb linkTitled')}
+            </DropdownMenuItem>
+            <DropdownMenuItem
+              onClick={() =>
+                run((v) =>
+                  labInsertSnippet(
+                    v,
+                    sliceRef,
+                    '![',
+                    'alt text',
+                    '](https://example.com/image.png "Image title")'
+                  )
+                )
+              }
+            >
+              <ImageIcon className="h-3.5 w-3.5 mr-2 inline" />
+              {t('Advanced lab tb imageTitled')}
+            </DropdownMenuItem>
+            <DropdownMenuSeparator />
+            <DropdownMenuItem onClick={() => run((v) => labInsertRaw(v, sliceRef, '  \n'))}>
+              <Pilcrow className="h-3.5 w-3.5 mr-2 inline" />
+              {t('Advanced lab tb hardBreak')}
+            </DropdownMenuItem>
           </DropdownMenuContent>
         </DropdownMenu>
 
@@ -240,10 +307,28 @@ export function AdvancedEventLabMarkupToolbar({
               <List className="h-3.5 w-3.5 mr-2 inline" />
               {t('Advanced lab tb bulletList')}
             </DropdownMenuItem>
+            <DropdownMenuItem onClick={() => run((v) => labInsertRaw(v, sliceRef, '\n* item one\n* item two\n'))}>
+              <List className="h-3.5 w-3.5 mr-2 inline" />
+              {t('Advanced lab tb bulletListStar')}
+            </DropdownMenuItem>
             <DropdownMenuItem onClick={() => run((v) => labInsertRaw(v, sliceRef, '\n1. first\n2. second\n'))}>
               <ListOrdered className="h-3.5 w-3.5 mr-2 inline" />
               {t('Advanced lab tb orderedList')}
             </DropdownMenuItem>
+            <DropdownMenuItem
+              onClick={() =>
+                run((v) =>
+                  labInsertRaw(
+                    v,
+                    sliceRef,
+                    '\n4. item starting at four\n5. next item\n'
+                  )
+                )
+              }
+            >
+              <ListOrdered className="h-3.5 w-3.5 mr-2 inline" />
+              {t('Advanced lab tb orderedListStart')}
+            </DropdownMenuItem>
             <DropdownMenuItem
               onClick={() =>
                 run((v) =>
@@ -454,16 +539,32 @@ export function AdvancedEventLabMarkupToolbar({
           </DropdownMenuContent>
         </DropdownMenu>
 
-        <Button
-          type="button"
-          variant="ghost"
-          size="sm"
-          className="h-8 text-xs shrink-0"
-          title={t('Advanced lab tb hrTitle')}
-          onClick={() => run((v) => labInsertRaw(v, sliceRef, '\n---\n'))}
-        >
-          <Minus className="h-3.5 w-3.5" />
-        </Button>
+        <DropdownMenu>
+          <DropdownMenuTrigger asChild>
+            <Button
+              type="button"
+              variant="ghost"
+              size="sm"
+              className="h-8 gap-1 text-xs shrink-0"
+              title={t('Advanced lab tb horizontalRules')}
+            >
+              <Minus className="h-3.5 w-3.5" />
+              <ChevronDown className="h-3 w-3 opacity-60" />
+            </Button>
+          </DropdownMenuTrigger>
+          <DropdownMenuContent align="start" className="z-[280] w-48">
+            <DropdownMenuLabel>{t('Advanced lab tb horizontalRules')}</DropdownMenuLabel>
+            <DropdownMenuItem onClick={() => run((v) => labInsertRaw(v, sliceRef, '\n---\n'))}>
+              {t('Advanced lab tb hrDashes')}
+            </DropdownMenuItem>
+            <DropdownMenuItem onClick={() => run((v) => labInsertRaw(v, sliceRef, '\n***\n'))}>
+              {t('Advanced lab tb hrAsterisks')}
+            </DropdownMenuItem>
+            <DropdownMenuItem onClick={() => run((v) => labInsertRaw(v, sliceRef, '\n___\n'))}>
+              {t('Advanced lab tb hrUnderscores')}
+            </DropdownMenuItem>
+          </DropdownMenuContent>
+        </DropdownMenu>
       </div>
     )
   }
diff --git a/src/components/Image/index.tsx b/src/components/Image/index.tsx
index 85d562a0..85fc3f34 100644
--- a/src/components/Image/index.tsx
+++ b/src/components/Image/index.tsx
@@ -50,6 +50,8 @@ export default function Image({
   holdUntilClick = false,
   fetchPriority,
   onClick,
+  /** Native tooltip on hover (e.g. Markdown `![alt](url "title")`). When set, overrides alt-as-title on `<img>`. */
+  tooltipTitle,
   ...props
 }: HTMLAttributes<HTMLSpanElement> & {
   classNames?: {
@@ -58,6 +60,8 @@ export default function Image({
   }
   image: TImetaInfo
   alt?: string
+  /** Shown as the `<img title>` tooltip when non-empty. */
+  tooltipTitle?: string
   hideIfError?: boolean
   errorPlaceholder?: React.ReactNode
   /** Passed to the inner `<img>` (e.g. profile banner vs avatar load order). */
@@ -93,6 +97,10 @@ export default function Image({
   const loadSettledRef = useRef(false)
 
   const finalAlt = imetaAlt || alt
+  const imgTitle =
+    tooltipTitle != null && String(tooltipTitle).trim() !== ''
+      ? String(tooltipTitle).trim()
+      : finalAlt || undefined
   const openLinkHref =
     (isSafeMediaUrl(url) && url.trim()) || (isSafeMediaUrl(imageUrl) && imageUrl.trim()) || ''
 
@@ -216,9 +224,15 @@ export default function Image({
     onClick?.(e)
   }
 
+  const titled = tooltipTitle != null && String(tooltipTitle).trim() !== ''
+
   return (
     <span
-      className={cn('relative overflow-hidden block w-full', classNames.wrapper)}
+      className={cn(
+        'relative overflow-hidden block w-full',
+        classNames.wrapper,
+        titled && 'cursor-help rounded-lg ring-1 ring-inset ring-dotted ring-muted-foreground/45'
+      )}
       style={mergedWrapperStyle}
       onClick={handleWrapperClick}
       {...props}
@@ -258,7 +272,7 @@ export default function Image({
           ref={imgRef}
           src={imageUrl}
           alt={finalAlt}
-          title={finalAlt || undefined}
+          title={imgTitle}
           referrerPolicy="no-referrer"
           decoding={effectiveHoldUntilClick ? 'async' : 'sync'}
           // `lazy` often never starts the request inside nested feed scrollers; always-load should fetch eagerly.
diff --git a/src/components/Note/MarkdownArticle/MarkdownArticle.tsx b/src/components/Note/MarkdownArticle/MarkdownArticle.tsx
index d799b92d..a43a66e6 100644
--- a/src/components/Note/MarkdownArticle/MarkdownArticle.tsx
+++ b/src/components/Note/MarkdownArticle/MarkdownArticle.tsx
@@ -23,6 +23,7 @@ import {
 } from '@/lib/url'
 import { getHttpUrlFromITags, getImetaInfosFromEvent } from '@/lib/event'
 import { canonicalizeRssArticleUrl } from '@/lib/rss-article'
+import { cn } from '@/lib/utils'
 import { Event, kinds } from 'nostr-tools'
 import Emoji from '@/components/Emoji'
 import {
@@ -613,16 +614,6 @@ function normalizeBackticks(content: string): string {
  * Note: Only converts if the text line has at least 2 characters to avoid
  * creating headers from fragments like "D\n------" which would become "## D"
  */
-/**
- * Normalize excessive newlines - reduce 3+ consecutive newlines (with optional whitespace) to exactly 2
- */
-function normalizeNewlines(content: string): string {
-  // Match sequences of 3 or more newlines with optional whitespace between them
-  // Pattern: newline, optional whitespace, newline, optional whitespace, one or more newlines
-  // Replace with exactly 2 newlines
-  return content.replace(/\n\s*\n\s*\n+/g, '\n\n')
-}
-
 /**
  * Normalize single newlines within bold/italic spans to spaces
  * This allows bold/italic formatting to work across single line breaks
@@ -3237,6 +3228,14 @@ function parseMarkdownContentMarked(
     }
   }
 
+  /** CommonMark / GFM optional title in `()` for links and images — surfaced as native `title` + hover cue. */
+  const markdownTokenTitle = (token: { title?: string | null }): string | undefined => {
+    const raw = token.title
+    if (raw == null) return undefined
+    const s = String(raw).trim()
+    return s.length > 0 ? s : undefined
+  }
+
   const renderInlineTokens = (tokens: any[], keyPrefix: string): React.ReactNode[] => {
     const out: React.ReactNode[] = []
     for (let i = 0; i < tokens.length; i++) {
@@ -3294,6 +3293,11 @@ function parseMarkdownContentMarked(
         }
         case 'link': {
           const href = String(token.href ?? '')
+          const linkTip = markdownTokenTitle(token)
+          const linkVisual = cn(
+            'text-green-600 dark:text-green-400 hover:text-green-700 dark:hover:text-green-300 hover:underline break-words',
+            linkTip && 'cursor-help underline decoration-dotted decoration-current/70 underline-offset-2'
+          )
           const children = stripNestedAnchorsFromNodes(
             renderInlineTokens(token.tokens ?? [{ type: 'text', text: token.text ?? href }], `${key}-link`),
             `${key}-link-sanitized`
@@ -3303,7 +3307,8 @@ function parseMarkdownContentMarked(
               <PaytoLink
                 key={`${key}-payto`}
                 paytoUri={href}
-                className="text-green-600 dark:text-green-400 hover:text-green-700 dark:hover:text-green-300 hover:underline break-words"
+                className={linkVisual}
+                linkTitle={linkTip}
               >
                 {children}
               </PaytoLink>
@@ -3315,7 +3320,8 @@ function parseMarkdownContentMarked(
                 href={href}
                 target="_blank"
                 rel="noopener noreferrer"
-                className="text-green-600 dark:text-green-400 hover:text-green-700 dark:hover:text-green-300 hover:underline break-words"
+                title={linkTip}
+                className={linkVisual}
               >
                 {children}
               </a>
@@ -3331,6 +3337,7 @@ function parseMarkdownContentMarked(
           const cleaned = cleanUrl(src)
           if (!cleaned) break
           const label = String(token.text ?? '')
+          const imageTip = markdownTokenTitle(token)
           if (isVideo(cleaned) || isAudio(cleaned) || isHlsPlaylistUrl(cleaned)) {
             const poster = videoPosterMap?.get(cleaned)
             out.push(
@@ -3366,6 +3373,7 @@ function parseMarkdownContentMarked(
               key={`${key}-img-inline`}
               image={{ ...baseImeta, url: src }}
               alt={label || 'image'}
+              tooltipTitle={imageTip}
               className="w-full rounded-lg cursor-zoom-in"
               classNames={{
                 wrapper: 'not-prose my-2 block max-w-[400px] mx-auto rounded-lg w-full',
@@ -4115,6 +4123,7 @@ function parseMarkdownContentMarked(
             key={`${key}-img-block`}
             image={imetaInfoForStandaloneImageUrl(cleaned)}
             alt={imageToken.text || 'image'}
+            tooltipTitle={markdownTokenTitle(imageToken)}
             className="w-full rounded-lg cursor-zoom-in my-0"
             classNames={{ wrapper: 'my-2 block max-w-[400px] mx-auto' }}
             holdUntilClick={lazyMedia}
@@ -4133,12 +4142,31 @@ function parseMarkdownContentMarked(
 
   const renderBlockTokens = (tokens: any[], keyPrefix: string): React.ReactNode[] => {
     const nodes: React.ReactNode[] = []
+    /** Marked emits `space` for inter-block newlines; ≥2 are required between blocks—extras are user intent. */
+    const spaceTokenExtraGapEm = (t: { raw?: string }): number => {
+      const raw = String(t.raw ?? '')
+      const newlineCount = raw.match(/\n/g)?.length ?? 0
+      const extraLines = Math.max(0, newlineCount - 2)
+      return Math.min(extraLines, 12) * 1.25
+    }
     for (let i = 0; i < tokens.length; i++) {
       const token = tokens[i]
       const key = `${keyPrefix}-${i}`
       switch (token.type) {
-        case 'space':
+        case 'space': {
+          const gapEm = spaceTokenExtraGapEm(token)
+          if (gapEm > 0) {
+            nodes.push(
+              <div
+                key={`${key}-space`}
+                className="not-prose pointer-events-none select-none"
+                aria-hidden
+                style={{ minHeight: `${gapEm}em` }}
+              />
+            )
+          }
           break
+        }
         case 'paragraph':
           nodes.push(renderParagraph(token, key))
           break
@@ -4268,7 +4296,9 @@ function parseMarkdownContentMarked(
 
           const listBody = React.createElement(
             ListTag,
-            { className: listClass },
+            token.ordered
+              ? { className: listClass, start: startNum }
+              : { className: listClass },
             items.map((item: any, itemIdx: number) => (
               <li
                 key={`${key}-li-${itemIdx}`}
@@ -5451,8 +5481,7 @@ export default function MarkdownArticle({
   const preprocessedContent = useMemo(() => {
     // First unescape JSON-encoded escape sequences
     let processed = unescapeJsonContent(event.content)
-    // Normalize excessive newlines (reduce 3+ to 2)
-    processed = normalizeNewlines(processed)
+    // Keep multi-newline runs intact so Marked `space` tokens can reproduce intentional vertical gaps.
     // Normalize single newlines within bold/italic spans to spaces
     processed = normalizeInlineFormattingNewlines(processed)
     // Normalize Setext-style headers (H1 with ===, H2 with ---)
@@ -5615,6 +5644,13 @@ export default function MarkdownArticle({
   return (
     <>
       <style>{`
+        /* Padding (not margin) so separation does not collapse with the prior list's margin */
+        .prose > div.break-words > ul + ul,
+        .prose > div.break-words > ul + ol,
+        .prose > div.break-words > ol + ul,
+        .prose > div.break-words > ol + ol {
+          padding-top: 0.75rem;
+        }
         .prose ol[class*="list-decimal"] {
           list-style-type: decimal !important;
         }
diff --git a/src/components/PaytoLink/index.tsx b/src/components/PaytoLink/index.tsx
index 622bac2b..41d62e83 100644
--- a/src/components/PaytoLink/index.tsx
+++ b/src/components/PaytoLink/index.tsx
@@ -23,7 +23,9 @@ export default function PaytoLink({
   pubkey,
   onOpenZap,
   className,
-  children
+  children,
+  /** When set (e.g. Markdown link title), used as the native `title` tooltip instead of the default payto hint. */
+  linkTitle
 }: {
   paytoUri?: string
   type?: string
@@ -33,6 +35,7 @@ export default function PaytoLink({
   onOpenZap?: (pubkey: string) => void
   className?: string
   children?: React.ReactNode
+  linkTitle?: string
 }) {
   const { t } = useTranslation()
   const [dialogOpen, setDialogOpen] = useState(false)
@@ -78,6 +81,7 @@ export default function PaytoLink({
   const iconChar = getPaytoIconChar(type)
   const profileUrl = getPaytoProfileUrl(type, authority)
   const content = children ?? <span className="break-all">{authority}</span>
+  const overrideTip = linkTitle?.trim()
 
   const iconEl = (
     <span className="shrink-0 flex items-center justify-center w-4 h-4 text-[1rem] leading-none" aria-hidden>
@@ -106,7 +110,10 @@ export default function PaytoLink({
           'text-primary hover:underline cursor-pointer text-left break-words inline-flex items-center gap-1.5',
           className
         )}
-        title={categoryLabel ? `${displayLabel} (${categoryLabel}): ${t('Open on website')}` : `${displayLabel}: ${t('Open on website')}`}
+        title={
+          overrideTip ||
+          (categoryLabel ? `${displayLabel} (${categoryLabel}): ${t('Open on website')}` : `${displayLabel}: ${t('Open on website')}`)
+        }
         onClick={(e) => e.stopPropagation()}
       >
         {iconEl}
@@ -124,7 +131,14 @@ export default function PaytoLink({
           'text-primary hover:underline cursor-pointer text-left break-words inline-flex items-center gap-1.5',
           className
         )}
-        title={known && categoryLabel ? `${displayLabel} (${categoryLabel}): ${t('Click to open payment options')}` : known ? `${displayLabel}: ${t('Click to open payment options')}` : t('Click to copy address')}
+        title={
+          overrideTip ||
+          (known && categoryLabel
+            ? `${displayLabel} (${categoryLabel}): ${t('Click to open payment options')}`
+            : known
+              ? `${displayLabel}: ${t('Click to open payment options')}`
+              : t('Click to copy address'))
+        }
       >
         {iconEl}
         {content}
diff --git a/src/i18n/locales/de.ts b/src/i18n/locales/de.ts
index f51f101f..4b591e37 100644
--- a/src/i18n/locales/de.ts
+++ b/src/i18n/locales/de.ts
@@ -989,17 +989,30 @@ export default {
     'Advanced lab tb h4': 'Überschrift 4 (####)',
     'Advanced lab tb h5': 'Überschrift 5 (#####)',
     'Advanced lab tb h6': 'Überschrift 6 (######)',
+    'Advanced lab tb setextH1': 'Setext-Überschrift 1 (Titel + ===)',
+    'Advanced lab tb setextH2': 'Setext-Überschrift 2 (Titel + ---)',
     'Advanced lab tb horizontalRule': 'Horizontale Linie (---)',
+    'Advanced lab tb horizontalRules': 'Horizontale Linien',
+    'Advanced lab tb hrDashes': 'Bindestriche (---)',
+    'Advanced lab tb hrAsterisks': 'Sterne (***)',
+    'Advanced lab tb hrUnderscores': 'Unterstriche (___)',
     'Advanced lab tb inline': 'Inline',
     'Advanced lab tb bold': 'Fett (** **)',
+    'Advanced lab tb boldUnderscore': 'Fett (__ __)',
     'Advanced lab tb italic': 'Kursiv (* *)',
+    'Advanced lab tb italicUnderscore': 'Kursiv (_ _)',
     'Advanced lab tb strike': 'Durchgestrichen (~~ ~~)',
     'Advanced lab tb inlineCode': 'Inline-Code (` `)',
     'Advanced lab tb link': 'Link [Text](URL)',
+    'Advanced lab tb linkTitled': 'Link mit Titel [Text](URL "Titel")',
     'Advanced lab tb image': 'Bild ![alt](URL)',
+    'Advanced lab tb imageTitled': 'Bild mit Titel ![alt](URL "Titel")',
+    'Advanced lab tb hardBreak': 'Harter Zeilenumbruch (zwei Leerzeichen + Zeilenumbruch)',
     'Advanced lab tb lists': 'Listen',
     'Advanced lab tb bulletList': 'Aufzählung (-)',
+    'Advanced lab tb bulletListStar': 'Aufzählung (*)',
     'Advanced lab tb orderedList': 'Nummerierte Liste (1.)',
+    'Advanced lab tb orderedListStart': 'Nummerierte Liste (Startnummer, z. B. 4.)',
     'Advanced lab tb taskItem': 'Aufgabe (- [ ])',
     'Advanced lab tb blocks': 'Blöcke',
     'Advanced lab tb blockquote': 'Zitat (>)',
diff --git a/src/i18n/locales/en.ts b/src/i18n/locales/en.ts
index 7485d219..e4bfd5e9 100644
--- a/src/i18n/locales/en.ts
+++ b/src/i18n/locales/en.ts
@@ -990,17 +990,30 @@ export default {
     'Advanced lab tb h4': 'Heading 4 (####)',
     'Advanced lab tb h5': 'Heading 5 (#####)',
     'Advanced lab tb h6': 'Heading 6 (######)',
+    'Advanced lab tb setextH1': 'Setext heading 1 (title + ===)',
+    'Advanced lab tb setextH2': 'Setext heading 2 (title + ---)',
     'Advanced lab tb horizontalRule': 'Horizontal rule (---)',
+    'Advanced lab tb horizontalRules': 'Horizontal rules',
+    'Advanced lab tb hrDashes': 'Dashes (---)',
+    'Advanced lab tb hrAsterisks': 'Asterisks (***)',
+    'Advanced lab tb hrUnderscores': 'Underscores (___)',
     'Advanced lab tb inline': 'Inline',
     'Advanced lab tb bold': 'Bold (** **)',
+    'Advanced lab tb boldUnderscore': 'Bold (__ __)',
     'Advanced lab tb italic': 'Italic (* *)',
+    'Advanced lab tb italicUnderscore': 'Italic (_ _)',
     'Advanced lab tb strike': 'Strikethrough (~~ ~~)',
     'Advanced lab tb inlineCode': 'Inline code (` `)',
     'Advanced lab tb link': 'Link [text](url)',
+    'Advanced lab tb linkTitled': 'Link with title [text](url "title")',
     'Advanced lab tb image': 'Image ![alt](url)',
+    'Advanced lab tb imageTitled': 'Image with title ![alt](url "title")',
+    'Advanced lab tb hardBreak': 'Hard line break (two spaces + newline)',
     'Advanced lab tb lists': 'Lists',
     'Advanced lab tb bulletList': 'Bullet list (-)',
+    'Advanced lab tb bulletListStar': 'Bullet list (*)',
     'Advanced lab tb orderedList': 'Numbered list (1.)',
+    'Advanced lab tb orderedListStart': 'Numbered list (custom start, e.g. 4.)',
     'Advanced lab tb taskItem': 'Task item (- [ ])',
     'Advanced lab tb blocks': 'Blocks',
     'Advanced lab tb blockquote': 'Blockquote (>)',