diff --git a/abogen/normalization_settings.py b/abogen/normalization_settings.py
index 2f300fa..5524100 100644
--- a/abogen/normalization_settings.py
+++ b/abogen/normalization_settings.py
@@ -34,6 +34,11 @@ _SETTINGS_DEFAULTS: Dict[str, Any] = {
     "normalization_titles": True,
     "normalization_terminal": True,
     "normalization_phoneme_hints": True,
+    "normalization_apostrophes_contractions": True,
+    "normalization_apostrophes_plural_possessives": True,
+    "normalization_apostrophes_sibilant_possessives": True,
+    "normalization_apostrophes_decades": True,
+    "normalization_apostrophes_leading_elisions": True,
     "normalization_apostrophe_mode": "spacy",
 }
 
@@ -151,6 +156,17 @@ def build_apostrophe_config(
     config = replace(base or ApostropheConfig())
     config.convert_numbers = bool(settings.get("normalization_numbers", True))
     config.add_phoneme_hints = bool(settings.get("normalization_phoneme_hints", True))
+    config.contraction_mode = "expand" if settings.get("normalization_apostrophes_contractions", True) else "keep"
+    config.plural_possessive_mode = (
+        "collapse" if settings.get("normalization_apostrophes_plural_possessives", True) else "keep"
+    )
+    config.sibilant_possessive_mode = (
+        "mark" if settings.get("normalization_apostrophes_sibilant_possessives", True) else "keep"
+    )
+    config.decades_mode = "expand" if settings.get("normalization_apostrophes_decades", True) else "keep"
+    config.leading_elision_mode = (
+        "expand" if settings.get("normalization_apostrophes_leading_elisions", True) else "keep"
+    )
     return config
 
 
diff --git a/abogen/web/conversion_runner.py b/abogen/web/conversion_runner.py
index d0e5d29..a7497fc 100644
--- a/abogen/web/conversion_runner.py
+++ b/abogen/web/conversion_runner.py
@@ -25,6 +25,7 @@ from abogen.normalization_settings import (
     build_apostrophe_config,
     build_llm_configuration,
     get_runtime_settings,
+    apply_overrides as apply_normalization_overrides,
 )
 from abogen.entity_analysis import normalize_token as normalize_entity_token
 from abogen.text_extractor import ExtractedChapter, extract_from_path
@@ -669,6 +670,20 @@ def _merge_metadata(
 _APOSTROPHE_CONFIG = ApostropheConfig()
 
 
+def _normalize_for_pipeline(
+    text: str,
+    *,
+    normalization_overrides: Optional[Mapping[str, Any]] = None,
+) -> str:
+    """Normalize text for tests or utilities with optional overrides."""
+
+    runtime_settings = get_runtime_settings()
+    if normalization_overrides:
+        runtime_settings = apply_normalization_overrides(runtime_settings, normalization_overrides)
+    apostrophe_config = build_apostrophe_config(settings=runtime_settings, base=_APOSTROPHE_CONFIG)
+    return normalize_for_pipeline(text, config=apostrophe_config, settings=runtime_settings)
+
+
 def _compile_pronunciation_rules(
     overrides: Optional[Iterable[Mapping[str, Any]]],
 ) -> List[Dict[str, Any]]:
@@ -1101,6 +1116,9 @@ def run_conversion_job(job: Job) -> None:
     canceller = _make_canceller(job)
 
     normalization_settings = get_runtime_settings()
+    job_overrides = getattr(job, "normalization_overrides", None)
+    if job_overrides:
+        normalization_settings = apply_normalization_overrides(normalization_settings, job_overrides)
     apostrophe_config = build_apostrophe_config(
         settings=normalization_settings,
         base=_APOSTROPHE_CONFIG,
diff --git a/abogen/web/routes.py b/abogen/web/routes.py
index 99c561b..9d5ccd5 100644
--- a/abogen/web/routes.py
+++ b/abogen/web/routes.py
@@ -1723,6 +1723,30 @@ def _apply_book_step_form(
     else:
         pending.normalize_chapter_opening_caps = caps_default
 
+    def _extract_checkbox(name: str, default: bool) -> bool:
+        values: List[str] = []
+        getter = getattr(form, "getlist", None)
+        if callable(getter):
+            raw_values = getter(name)
+            if raw_values:
+                values = list(cast(Iterable[str], raw_values))
+        else:
+            raw_flag = form.get(name)
+            if raw_flag is not None:
+                values = [raw_flag]
+        if values:
+            return _coerce_bool(values[-1], default)
+        if hasattr(form, "__contains__") and name in form:
+            return False
+        return default
+
+    overrides_existing = getattr(pending, "normalization_overrides", None)
+    overrides: Dict[str, bool] = dict(overrides_existing or {})
+    for key in _APOSTROPHE_OVERRIDE_KEYS:
+        default_toggle = overrides.get(key, bool(settings.get(key, True)))
+        overrides[key] = _extract_checkbox(key, default_toggle)
+    pending.normalization_overrides = overrides
+
     speed_value = form.get("speed")
     if speed_value is not None:
         try:
@@ -1977,11 +2001,24 @@ BOOLEAN_SETTINGS = {
     "normalization_titles",
     "normalization_terminal",
     "normalization_phoneme_hints",
+    "normalization_apostrophes_contractions",
+    "normalization_apostrophes_plural_possessives",
+    "normalization_apostrophes_sibilant_possessives",
+    "normalization_apostrophes_decades",
+    "normalization_apostrophes_leading_elisions",
 }
 
 FLOAT_SETTINGS = {"silence_between_chapters", "chapter_intro_delay", "llm_timeout"}
 INT_SETTINGS = {"max_subtitle_words", "speaker_analysis_threshold"}
 
+_APOSTROPHE_OVERRIDE_KEYS = (
+    "normalization_apostrophes_contractions",
+    "normalization_apostrophes_plural_possessives",
+    "normalization_apostrophes_sibilant_possessives",
+    "normalization_apostrophes_decades",
+    "normalization_apostrophes_leading_elisions",
+)
+
 
 def _integration_defaults() -> Dict[str, Dict[str, Any]]:
     return {
@@ -2047,6 +2084,11 @@ def _settings_defaults() -> Dict[str, Any]:
         "normalization_titles": True,
         "normalization_terminal": True,
         "normalization_phoneme_hints": True,
+        "normalization_apostrophes_contractions": True,
+        "normalization_apostrophes_plural_possessives": True,
+        "normalization_apostrophes_sibilant_possessives": True,
+        "normalization_apostrophes_decades": True,
+        "normalization_apostrophes_leading_elisions": True,
         "normalization_apostrophe_mode": "spacy",
     }
 
@@ -3125,6 +3167,11 @@ def api_normalization_preview() -> ResponseReturnValue:
         "normalization_titles",
         "normalization_terminal",
         "normalization_phoneme_hints",
+        "normalization_apostrophes_contractions",
+        "normalization_apostrophes_plural_possessives",
+        "normalization_apostrophes_sibilant_possessives",
+        "normalization_apostrophes_decades",
+        "normalization_apostrophes_leading_elisions",
     )
     for key in boolean_keys:
         if key in normalization_payload:
@@ -4076,6 +4123,9 @@ def _build_pending_job_from_extraction(
         max_subtitle_words=max_subtitle_words,
         metadata_tags=metadata_tags,
         chapters=chapters_payload,
+        normalization_overrides={
+            key: bool(settings.get(key, True)) for key in _APOSTROPHE_OVERRIDE_KEYS
+        },
         created_at=time.time(),
         cover_image_path=cover_path,
         cover_image_mime=cover_mime,
@@ -4455,6 +4505,7 @@ def finalize_job(pending_id: str) -> ResponseReturnValue:
         entity_summary=pending.entity_summary,
         manual_overrides=pending.manual_overrides,
         pronunciation_overrides=pending.pronunciation_overrides,
+        normalization_overrides=pending.normalization_overrides,
     )
 
     if config_languages:
diff --git a/abogen/web/service.py b/abogen/web/service.py
index 0794450..20c0773 100644
--- a/abogen/web/service.py
+++ b/abogen/web/service.py
@@ -148,6 +148,7 @@ class Job:
     entity_summary: Dict[str, Any] = field(default_factory=dict)
     manual_overrides: List[Dict[str, Any]] = field(default_factory=list)
     pronunciation_overrides: List[Dict[str, Any]] = field(default_factory=list)
+    normalization_overrides: Dict[str, Any] = field(default_factory=dict)
 
     def add_log(self, message: str, level: str = "info") -> None:
         entry = JobLog(timestamp=time.time(), message=message, level=level)
@@ -216,6 +217,7 @@ class Job:
             "entity_summary": dict(self.entity_summary),
             "manual_overrides": [dict(entry) for entry in self.manual_overrides],
             "pronunciation_overrides": [dict(entry) for entry in self.pronunciation_overrides],
+            "normalization_overrides": dict(self.normalization_overrides),
         }
 
 
@@ -431,6 +433,7 @@ class PendingJob:
     max_subtitle_words: int
     metadata_tags: Dict[str, Any]
     chapters: List[Dict[str, Any]]
+    normalization_overrides: Dict[str, Any]
     created_at: float
     cover_image_path: Optional[Path] = None
     cover_image_mime: Optional[str] = None
@@ -531,6 +534,7 @@ class ConversionService:
         entity_summary: Optional[Mapping[str, Any]] = None,
         manual_overrides: Optional[Iterable[Mapping[str, Any]]] = None,
         pronunciation_overrides: Optional[Iterable[Mapping[str, Any]]] = None,
+        normalization_overrides: Optional[Mapping[str, Any]] = None,
     ) -> Job:
         job_id = uuid.uuid4().hex
         normalized_metadata = self._normalize_metadata_tags(metadata_tags)
@@ -580,6 +584,7 @@ class ConversionService:
             entity_summary=dict(entity_summary or {}),
             manual_overrides=[dict(entry) for entry in manual_overrides] if manual_overrides else [],
             pronunciation_overrides=[dict(entry) for entry in pronunciation_overrides] if pronunciation_overrides else [],
+            normalization_overrides=dict(normalization_overrides or {}),
         )
         with self._lock:
             self._jobs[job_id] = job
@@ -737,6 +742,7 @@ class ConversionService:
                 entity_summary=job.entity_summary,
                 manual_overrides=job.manual_overrides,
                 pronunciation_overrides=job.pronunciation_overrides,
+                normalization_overrides=job.normalization_overrides,
             )
 
             new_job.speaker_voice_languages = list(job.speaker_voice_languages)
@@ -1039,6 +1045,7 @@ class ConversionService:
             "entity_summary": dict(job.entity_summary),
             "manual_overrides": [dict(entry) for entry in job.manual_overrides],
             "pronunciation_overrides": [dict(entry) for entry in job.pronunciation_overrides],
+            "normalization_overrides": dict(job.normalization_overrides),
         }
 
     def _persist_state(self) -> None:
@@ -1164,6 +1171,7 @@ class ConversionService:
         job.pronunciation_overrides = [
             dict(entry) for entry in payload.get("pronunciation_overrides", []) if isinstance(entry, Mapping)
         ]
+        job.normalization_overrides = dict(payload.get("normalization_overrides", {}) or {})
         job.pause_event.set()
         return job
 
diff --git a/abogen/web/static/settings.js b/abogen/web/static/settings.js
index f7631ed..c65f4e3 100644
--- a/abogen/web/static/settings.js
+++ b/abogen/web/static/settings.js
@@ -264,6 +264,11 @@ function collectNormalizationSettings() {
     normalization_titles: Boolean(form.querySelector('input[name="normalization_titles"]')?.checked),
     normalization_terminal: Boolean(form.querySelector('input[name="normalization_terminal"]')?.checked),
     normalization_phoneme_hints: Boolean(form.querySelector('input[name="normalization_phoneme_hints"]')?.checked),
+    normalization_apostrophes_contractions: Boolean(form.querySelector('input[name="normalization_apostrophes_contractions"]')?.checked),
+    normalization_apostrophes_plural_possessives: Boolean(form.querySelector('input[name="normalization_apostrophes_plural_possessives"]')?.checked),
+    normalization_apostrophes_sibilant_possessives: Boolean(form.querySelector('input[name="normalization_apostrophes_sibilant_possessives"]')?.checked),
+    normalization_apostrophes_decades: Boolean(form.querySelector('input[name="normalization_apostrophes_decades"]')?.checked),
+    normalization_apostrophes_leading_elisions: Boolean(form.querySelector('input[name="normalization_apostrophes_leading_elisions"]')?.checked),
     normalization_apostrophe_mode: form.querySelector('input[name="normalization_apostrophe_mode"]:checked')?.value || 'spacy',
   };
   return normalization;
diff --git a/abogen/web/templates/partials/new_job_step_book.html b/abogen/web/templates/partials/new_job_step_book.html
index aa30fed..b10013b 100644
--- a/abogen/web/templates/partials/new_job_step_book.html
+++ b/abogen/web/templates/partials/new_job_step_book.html
@@ -112,6 +112,34 @@
 {% else %}
   {% set narrator_voice = settings_dict.get('default_voice', options.voices[0] if options.voices else '') %}
 {% endif %}
+{% set normalization_overrides = pending.normalization_overrides if pending and pending.normalization_overrides else {} %}
+{% set apostrophe_toggles = [
+  {
+    'name': 'normalization_apostrophes_contractions',
+    'label': "Expand contractions (it's -> it is)",
+    'value': normalization_overrides.get('normalization_apostrophes_contractions', settings_dict.get('normalization_apostrophes_contractions', True)),
+  },
+  {
+    'name': 'normalization_apostrophes_plural_possessives',
+    'label': "Collapse plural possessives (dogs' -> dogs)",
+    'value': normalization_overrides.get('normalization_apostrophes_plural_possessives', settings_dict.get('normalization_apostrophes_plural_possessives', True)),
+  },
+  {
+    'name': 'normalization_apostrophes_sibilant_possessives',
+    'label': "Mark sibilant possessives (boss's -> boss + IZ marker)",
+    'value': normalization_overrides.get('normalization_apostrophes_sibilant_possessives', settings_dict.get('normalization_apostrophes_sibilant_possessives', True)),
+  },
+  {
+    'name': 'normalization_apostrophes_decades',
+    'label': "Expand decades ('90s -> 1990s)",
+    'value': normalization_overrides.get('normalization_apostrophes_decades', settings_dict.get('normalization_apostrophes_decades', True)),
+  },
+  {
+    'name': 'normalization_apostrophes_leading_elisions',
+    'label': "Expand leading elisions ('tis -> it is)",
+    'value': normalization_overrides.get('normalization_apostrophes_leading_elisions', settings_dict.get('normalization_apostrophes_leading_elisions', True)),
+  },
+] %}
 {% set voice_formula_value = '' %}
 {% set profile_value = narrator_profile if narrator_profile else '__standard' %}
 {% if profile_value == '__formula' %}
@@ -253,6 +281,21 @@
       </div>
     </section>
 
+    <section class="form-section">
+      <h3 class="form-section__title">Text normalization</h3>
+      <div class="field-grid field-grid--compact">
+        {% for toggle in apostrophe_toggles %}
+        <div class="field field--stack">
+          <label class="toggle-pill">
+            <input type="hidden" name="{{ toggle.name }}" value="false">
+            <input type="checkbox" name="{{ toggle.name }}" value="true" {% if toggle.value %}checked{% endif %} {{ 'disabled' if readonly else '' }}>
+            <span>{{ toggle.label }}</span>
+          </label>
+        </div>
+        {% endfor %}
+      </div>
+    </section>
+
     <section class="form-section">
       <h3 class="form-section__title">Entities &amp; casting</h3>
       <div class="field-grid field-grid--compact">
diff --git a/abogen/web/templates/settings.html b/abogen/web/templates/settings.html
index afe9dc9..193ec6f 100644
--- a/abogen/web/templates/settings.html
+++ b/abogen/web/templates/settings.html
@@ -269,6 +269,27 @@
                 <input type="checkbox" name="normalization_phoneme_hints" value="true" {% if settings.normalization_phoneme_hints %}checked{% endif %}>
                 <span>Add phoneme hints for possessives</span>
               </label>
+              <span class="field__caption">Apostrophes</span>
+              <label class="toggle-pill">
+                <input type="checkbox" name="normalization_apostrophes_contractions" value="true" {% if settings.normalization_apostrophes_contractions %}checked{% endif %}>
+                <span>Expand contractions ("it's" -> "it is")</span>
+              </label>
+              <label class="toggle-pill">
+                <input type="checkbox" name="normalization_apostrophes_plural_possessives" value="true" {% if settings.normalization_apostrophes_plural_possessives %}checked{% endif %}>
+                <span>Collapse plural possessives (dogs' -> dogs)</span>
+              </label>
+              <label class="toggle-pill">
+                <input type="checkbox" name="normalization_apostrophes_sibilant_possessives" value="true" {% if settings.normalization_apostrophes_sibilant_possessives %}checked{% endif %}>
+                <span>Add guidance for sibilant possessives (boss's -> boss + IZ marker)</span>
+              </label>
+              <label class="toggle-pill">
+                <input type="checkbox" name="normalization_apostrophes_decades" value="true" {% if settings.normalization_apostrophes_decades %}checked{% endif %}>
+                <span>Expand decades ('90s -> 1990s)</span>
+              </label>
+              <label class="toggle-pill">
+                <input type="checkbox" name="normalization_apostrophes_leading_elisions" value="true" {% if settings.normalization_apostrophes_leading_elisions %}checked{% endif %}>
+                <span>Expand leading elisions ('tis -> it is)</span>
+              </label>
             </div>
             <div class="field">
               <span class="field__label">Apostrophe strategy</span>
diff --git a/tests/test_prepare_form.py b/tests/test_prepare_form.py
index 4df8fa8..25cbfb2 100644
--- a/tests/test_prepare_form.py
+++ b/tests/test_prepare_form.py
@@ -31,6 +31,7 @@ def _make_pending_job() -> PendingJob:
         max_subtitle_words=50,
         metadata_tags={},
         chapters=[],
+        normalization_overrides={},
         created_at=0.0,
         read_title_intro=False,
         normalize_chapter_opening_caps=True,
diff --git a/tests/test_text_normalization.py b/tests/test_text_normalization.py
index cf7dab5..76ac32e 100644
--- a/tests/test_text_normalization.py
+++ b/tests/test_text_normalization.py
@@ -78,3 +78,28 @@ def test_numeric_ranges_are_spoken_with_to() -> None:
 def test_simple_fractions_are_spoken() -> None:
     normalized = _normalize_for_pipeline("Add 1/2 cup of sugar")
     assert "one half" in normalized.lower()
+
+
+def test_contractions_can_be_kept_when_override_disabled() -> None:
+    normalized = _normalize_for_pipeline(
+        "It's a good day.",
+        normalization_overrides={"normalization_apostrophes_contractions": False},
+    )
+    assert "It's" in normalized
+
+
+def test_sibilant_possessives_remain_when_marking_disabled() -> None:
+    normalized = _normalize_for_pipeline(
+        "The boss's chair wobbled.",
+        normalization_overrides={"normalization_apostrophes_sibilant_possessives": False},
+    )
+    assert "boss's" in normalized
+    assert "boss iz" not in normalized.lower()
+
+
+def test_decades_can_skip_expansion_when_disabled() -> None:
+    normalized = _normalize_for_pipeline(
+        "Classic hits from the '90s filled the hall.",
+        normalization_overrides={"normalization_apostrophes_decades": False},
+    )
+    assert "'90s" in normalized