diff --git a/lib/mail.js b/lib/mail.js
index 000d111..7629c4d 100644
--- a/lib/mail.js
+++ b/lib/mail.js
@@ -72,10 +72,55 @@ const Mail = {
     };
     walk(fullPart);
     if (plain.trim()) return plain;
-    if (html.trim()) return html.replace(/<[^>]+>/g, " ").replace(/\s+/g, " ").trim();
+    if (html.trim()) return this._htmlToText(html);
     return "";
   },
 
+  /**
+   * Macht aus HTML lesbaren Klartext: entfernt style/script/head-INHALTE komplett,
+   * leitet aus Block-Elementen Zeilenumbrüche ab, dekodiert Entities und glättet
+   * Whitespace – ohne Absatzstruktur platt zu walzen.
+   */
+  _htmlToText(html) {
+    let s = String(html);
+    s = s.replace(/<!--[\s\S]*?-->/g, " ");
+    // style/script/head/title inkl. Inhalt raus (sonst landet CSS/JS im Text).
+    s = s.replace(/<(style|script|head|title)\b[^>]*>[\s\S]*?<\/\1\s*>/gi, " ");
+    // Block-Grenzen -> Zeilenumbruch; Listenpunkte -> "- ".
+    s = s.replace(/<\s*br\s*\/?>/gi, "\n");
+    s = s.replace(/<\s*li\b[^>]*>/gi, "\n- ");
+    s = s.replace(/<\/\s*(p|div|li|tr|h[1-6]|ul|ol|table|blockquote)\s*>/gi, "\n");
+    s = s.replace(/<\/\s*td\s*>/gi, " ");
+    // Restliche Tags entfernen, Entities dekodieren.
+    s = s.replace(/<[^>]+>/g, " ");
+    s = this._decodeEntities(s);
+    // Whitespace glätten: Spaces/Tabs/NBSP zusammenfassen, Leerzeilen begrenzen.
+    s = s.replace(/[ \t ]+/g, " ");
+    s = s.replace(/ *\n */g, "\n");
+    s = s.replace(/\n{3,}/g, "\n\n");
+    return s.trim();
+  },
+
+  _decodeEntities(s) {
+    const named = {
+      amp: "&", lt: "<", gt: ">", quot: '"', apos: "'", nbsp: " ",
+      auml: "ä", ouml: "ö", uuml: "ü", Auml: "Ä", Ouml: "Ö", Uuml: "Ü", szlig: "ß",
+      euro: "€", copy: "©", reg: "®", trade: "™", hellip: "…", middot: "·", bull: "•",
+      ndash: "–", mdash: "—", laquo: "«", raquo: "»", deg: "°", eacute: "é", agrave: "à",
+      ldquo: "“", rdquo: "”", lsquo: "‘", rsquo: "’",
+      bdquo: "„", sbquo: "‚",
+    };
+    return String(s)
+      .replace(/&#x([0-9a-fA-F]+);/g, (_, h) => this._fromCp(parseInt(h, 16)))
+      .replace(/&#(\d+);/g, (_, d) => this._fromCp(parseInt(d, 10)))
+      .replace(/&([a-zA-Z][a-zA-Z0-9]*);/g, (m, n) => (named[n] != null ? named[n] : m));
+  },
+
+  _fromCp(cp) {
+    try { return Number.isFinite(cp) ? String.fromCodePoint(cp) : ""; }
+    catch (_) { return ""; }
+  },
+
   _parseAddress(str) {
     if (!str) return { name: "", email: "" };
     const m = str.match(/^\s*"?([^"<]*)"?\s*<([^>]+)>\s*$/);
diff --git a/lib/pdf.js b/lib/pdf.js
index 2283858..019a0f8 100644
--- a/lib/pdf.js
+++ b/lib/pdf.js
@@ -129,9 +129,27 @@ const Pdf = {
     return this._toLatin1(s).replace(/[\\()]/g, "\\$&");
   },
 
+  // Unicode-Sonderzeichen, die NICHT in Latin-1, aber in WinAnsiEncoding liegen
+  // (0x80–0x9F). Da die Schrift /WinAnsiEncoding nutzt und Bytes per charCodeAt&0xFF
+  // geschrieben werden, rendern diese so als echte Typografie-Zeichen statt als '?'.
+  _WINANSI: {
+    "€": 0x80, "‚": 0x82, "ƒ": 0x83, "„": 0x84, "…": 0x85,
+    "†": 0x86, "‡": 0x87, "ˆ": 0x88, "‰": 0x89, "Š": 0x8A,
+    "‹": 0x8B, "Œ": 0x8C, "Ž": 0x8E, "‘": 0x91, "’": 0x92,
+    "“": 0x93, "”": 0x94, "•": 0x95, "–": 0x96, "—": 0x97,
+    "˜": 0x98, "™": 0x99, "š": 0x9A, "›": 0x9B, "œ": 0x9C,
+    "ž": 0x9E, "Ÿ": 0x9F,
+  },
+
   _toLatin1(s) {
-    // Zeichen außerhalb Latin-1 durch '?' ersetzen.
-    return (s || "").replace(/[^\x00-\xFF]/g, "?");
+    let out = "";
+    for (const ch of (s || "")) {
+      const cp = ch.codePointAt(0);
+      if (cp <= 0xff) out += ch;                                  // Latin-1 direkt
+      else if (this._WINANSI[ch] != null) out += String.fromCharCode(this._WINANSI[ch]);
+      else out += "?";                                            // nicht darstellbar
+    }
+    return out;
   },
 
   _latin1Bytes(str) {