diff --git a/gateway/platforms/base.py b/gateway/platforms/base.py
index af74265d9a1..660be2e92d5 100644
--- a/gateway/platforms/base.py
+++ b/gateway/platforms/base.py
@@ -1510,11 +1510,20 @@ _MEDIA_EXT_ALTERNATION = "|".join(
 # consumer so both behave identically.
 # Path anchors: ``~/`` (Unix home-relative), ``/`` (Unix absolute),
 # ``X:\\`` or ``X:/`` (Windows drive-letter absolute — #34632).
+# Emphasis tolerance: models routinely wrap the tag in Markdown emphasis
+# (``**MEDIA:/x.pdf**``, ``*MEDIA:/x.pdf*``, ``_MEDIA:/x.pdf_``) when they
+# present a file to the user. The old single-quote anchor (``[`"']?``) and the
+# closing lookahead (which lacked ``*``/``_``) failed to match such tags, so the
+# file was silently never delivered and the literal ``MEDIA:`` text leaked into
+# the chat. Allow a short run of emphasis/quote markers on both sides so the tag
+# is recognised regardless of cosmetic Markdown. Code-block / inline-code /
+# blockquote contexts are still neutralised earlier by ``_mask_protected_spans``
+# (#35695), so example tags remain non-deliverable.
 MEDIA_TAG_CLEANUP_RE = re.compile(
-    r'''[`"']?MEDIA:\s*'''
+    r'''[`"'*_]{0,3}MEDIA:\s*'''
     r'''(?P<path>`[^`\n]+`|"[^"\n]+"|'[^'\n]+'|'''
     r'''(?:~/|/|[A-Za-z]:[/\\])\S+(?:[^\S\n]+\S+)*?\.(?:''' + _MEDIA_EXT_ALTERNATION + r'''))'''
-    r'''(?=[\s`"',;:)\]}\[]|$)[`"']?''',
+    r'''(?=[\s`"'*_,;:)\]}\[]|$)[`"'*_]{0,3}''',
     re.IGNORECASE,
 )
 
@@ -1529,10 +1538,10 @@ MEDIA_TAG_CLEANUP_RE = re.compile(
 # prompt-injection paths that do not validate are left visible instead of
 # silently dropped.
 MEDIA_EXTENSIONLESS_TAG_RE = re.compile(
-    r'''[`"']?MEDIA:\s*'''
+    r'''[`"'*_]{0,3}MEDIA:\s*'''
     r'''(?P<path>`[^`\n]+`|"[^"\n]+"|'[^'\n]+'|'''
     r'''(?:~/|/|[A-Za-z]:[/\\])[^\s\n`"']+)'''
-    r'''[`"']?\s*''',
+    r'''[`"'*_]{0,3}\s*''',
     re.IGNORECASE,
 )
 
diff --git a/tests/gateway/test_platform_base.py b/tests/gateway/test_platform_base.py
index 0f1d5c9901d..7b4170f457a 100644
--- a/tests/gateway/test_platform_base.py
+++ b/tests/gateway/test_platform_base.py
@@ -529,6 +529,51 @@ class TestExtractMedia:
         assert [p for p, _ in media] == ["/r/a.png"]
         assert "`MEDIA:/ex/b.png`" in cleaned
 
+    # --- Markdown emphasis wrapping tolerance ---
+    # Models routinely present a file as **MEDIA:/path** / *MEDIA:/path* /
+    # _MEDIA:/path_. The old pattern only tolerated a single quote/backtick, so
+    # the emphasis prevented the match and the file was silently never
+    # delivered (the literal MEDIA: text leaked into the chat instead).
+
+    def test_media_bold_wrapped_extracted(self):
+        media, cleaned = BasePlatformAdapter.extract_media(
+            "**MEDIA:/home/u/report.pptx**"
+        )
+        assert media == [("/home/u/report.pptx", False)]
+        assert "MEDIA:" not in cleaned
+
+    def test_media_italic_asterisk_extracted(self):
+        media, _ = BasePlatformAdapter.extract_media("*MEDIA:/home/u/report.pdf*")
+        assert media == [("/home/u/report.pdf", False)]
+
+    def test_media_italic_underscore_extracted(self):
+        media, _ = BasePlatformAdapter.extract_media("_MEDIA:/home/u/report.pdf_")
+        assert media == [("/home/u/report.pdf", False)]
+
+    def test_media_bold_mid_prose_extracted_and_stripped(self):
+        media, cleaned = BasePlatformAdapter.extract_media(
+            "Voici votre fichier **MEDIA:/tmp/r.pdf** bonne lecture"
+        )
+        assert media == [("/tmp/r.pdf", False)]
+        assert "MEDIA:" not in cleaned
+        assert "bonne lecture" in cleaned
+
+    def test_media_bold_wrapped_html_extracted(self):
+        # .html is a recognised extension; emphasis was the only blocker.
+        media, _ = BasePlatformAdapter.extract_media("**MEDIA:/srv/page.html**")
+        assert media == [("/srv/page.html", False)]
+
+    def test_media_underscore_in_filename_unaffected(self):
+        # Emphasis tolerance must not eat a legitimate '_' inside the path.
+        media, _ = BasePlatformAdapter.extract_media("MEDIA:/tmp/my_report_v2.pptx")
+        assert media == [("/tmp/my_report_v2.pptx", False)]
+
+    def test_media_bold_relative_path_still_ignored(self):
+        # The absolute-path anchor must still reject relative paths even when
+        # wrapped in emphasis.
+        media, _ = BasePlatformAdapter.extract_media("**MEDIA:report.html**")
+        assert media == []
+
 
 class TestMediaInsideSerializedJson:
     """Regression coverage for #34375 — MEDIA: embedded in serialized JSON