diff --git a/homeassistant/components/conversation/manifest.json b/homeassistant/components/conversation/manifest.json
index 979ea7538c4..7ca1799b2d1 100644
--- a/homeassistant/components/conversation/manifest.json
+++ b/homeassistant/components/conversation/manifest.json
@@ -6,5 +6,5 @@
   "documentation": "https://www.home-assistant.io/integrations/conversation",
   "integration_type": "system",
   "quality_scale": "internal",
-  "requirements": ["hassil==2.1.0", "home-assistant-intents==2025.1.1"]
+  "requirements": ["hassil==2.2.0", "home-assistant-intents==2025.1.1"]
 }
diff --git a/homeassistant/components/conversation/trigger.py b/homeassistant/components/conversation/trigger.py
index 634ae1fd9aa..752e294a8b3 100644
--- a/homeassistant/components/conversation/trigger.py
+++ b/homeassistant/components/conversation/trigger.py
@@ -5,7 +5,12 @@ from __future__ import annotations
 from typing import Any
 
 from hassil.recognize import RecognizeResult
-from hassil.util import PUNCTUATION_ALL
+from hassil.util import (
+    PUNCTUATION_END,
+    PUNCTUATION_END_WORD,
+    PUNCTUATION_START,
+    PUNCTUATION_START_WORD,
+)
 import voluptuous as vol
 
 from homeassistant.const import CONF_COMMAND, CONF_PLATFORM
@@ -22,7 +27,12 @@ from .models import ConversationInput
 def has_no_punctuation(value: list[str]) -> list[str]:
     """Validate result does not contain punctuation."""
     for sentence in value:
-        if PUNCTUATION_ALL.search(sentence):
+        if (
+            PUNCTUATION_START.search(sentence)
+            or PUNCTUATION_END.search(sentence)
+            or PUNCTUATION_START_WORD.search(sentence)
+            or PUNCTUATION_END_WORD.search(sentence)
+        ):
             raise vol.Invalid("sentence should not contain punctuation")
 
     return value
diff --git a/homeassistant/package_constraints.txt b/homeassistant/package_constraints.txt
index e147ce58c57..51393c2a516 100644
--- a/homeassistant/package_constraints.txt
+++ b/homeassistant/package_constraints.txt
@@ -35,7 +35,7 @@ go2rtc-client==0.1.2
 ha-ffmpeg==3.2.2
 habluetooth==3.13.0
 hass-nabucasa==0.88.1
-hassil==2.1.0
+hassil==2.2.0
 home-assistant-bluetooth==1.13.0
 home-assistant-frontend==20250109.2
 home-assistant-intents==2025.1.1
diff --git a/requirements_all.txt b/requirements_all.txt
index ba11e9c0d6d..a366b5f2f32 100644
--- a/requirements_all.txt
+++ b/requirements_all.txt
@@ -1109,7 +1109,7 @@ hass-nabucasa==0.88.1
 hass-splunk==0.1.1
 
 # homeassistant.components.conversation
-hassil==2.1.0
+hassil==2.2.0
 
 # homeassistant.components.jewish_calendar
 hdate==0.11.1
diff --git a/requirements_test_all.txt b/requirements_test_all.txt
index 4f7bf17edda..a8e934d8dd2 100644
--- a/requirements_test_all.txt
+++ b/requirements_test_all.txt
@@ -947,7 +947,7 @@ habluetooth==3.13.0
 hass-nabucasa==0.88.1
 
 # homeassistant.components.conversation
-hassil==2.1.0
+hassil==2.2.0
 
 # homeassistant.components.jewish_calendar
 hdate==0.11.1
diff --git a/script/hassfest/docker/Dockerfile b/script/hassfest/docker/Dockerfile
index 21b98d30f1e..5700ca01462 100644
--- a/script/hassfest/docker/Dockerfile
+++ b/script/hassfest/docker/Dockerfile
@@ -25,7 +25,7 @@ RUN --mount=from=ghcr.io/astral-sh/uv:0.5.21,source=/uv,target=/bin/uv \
         -c /usr/src/homeassistant/homeassistant/package_constraints.txt \
         -r /usr/src/homeassistant/requirements.txt \
         stdlib-list==0.10.0 pipdeptree==2.23.4 tqdm==4.66.5 ruff==0.9.1 \
-        PyTurboJPEG==1.7.5 go2rtc-client==0.1.2 ha-ffmpeg==3.2.2 hassil==2.1.0 home-assistant-intents==2025.1.1 mutagen==1.47.0 pymicro-vad==1.0.1 pyspeex-noise==1.0.2
+        PyTurboJPEG==1.7.5 go2rtc-client==0.1.2 ha-ffmpeg==3.2.2 hassil==2.2.0 home-assistant-intents==2025.1.1 mutagen==1.47.0 pymicro-vad==1.0.1 pyspeex-noise==1.0.2
 
 LABEL "name"="hassfest"
 LABEL "maintainer"="Home Assistant <hello@home-assistant.io>"
diff --git a/tests/components/conversation/snapshots/test_http.ambr b/tests/components/conversation/snapshots/test_http.ambr
index 1102a41e6c3..3e71ee99382 100644
--- a/tests/components/conversation/snapshots/test_http.ambr
+++ b/tests/components/conversation/snapshots/test_http.ambr
@@ -638,7 +638,7 @@
           'brightness': dict({
             'name': 'brightness',
             'text': '100',
-            'value': 100,
+            'value': 100.0,
           }),
           'name': dict({
             'name': 'name',
@@ -690,7 +690,7 @@
         'targets': dict({
         }),
         'unmatched_slots': dict({
-          'brightness': 1001,
+          'brightness': 1001.0,
         }),
       }),
     ]),