diff --git a/cli.py b/cli.py
index aec48aef7..1ba5071ed 100644
--- a/cli.py
+++ b/cli.py
@@ -1155,11 +1155,11 @@ def _strip_markdown_syntax(text: str) -> str:
     plain = re.sub(r"!\[([^\]]*)\]\([^\)]*\)", r"\1", plain)
     plain = re.sub(r"\[([^\]]+)\]\([^\)]*\)", r"\1", plain)
     plain = re.sub(r"\*\*\*([^*]+)\*\*\*", r"\1", plain)
-    plain = re.sub(r"___([^_]+)___", r"\1", plain)
+    plain = re.sub(r"(?<!\w)___([^_]+)___(?!\w)", r"\1", plain)
     plain = re.sub(r"\*\*([^*]+)\*\*", r"\1", plain)
-    plain = re.sub(r"__([^_]+)__", r"\1", plain)
+    plain = re.sub(r"(?<!\w)__([^_]+)__(?!\w)", r"\1", plain)
     plain = re.sub(r"\*([^*]+)\*", r"\1", plain)
-    plain = re.sub(r"_([^_]+)_", r"\1", plain)
+    plain = re.sub(r"(?<!\w)_([^_]+)_(?!\w)", r"\1", plain)
     plain = re.sub(r"~~([^~]+)~~", r"\1", plain)
     plain = re.sub(r"\n{3,}", "\n\n", plain)
     return plain.strip("\n")
diff --git a/tests/cli/test_cli_markdown_rendering.py b/tests/cli/test_cli_markdown_rendering.py
index 97ed1c751..01f0bab6c 100644
--- a/tests/cli/test_cli_markdown_rendering.py
+++ b/tests/cli/test_cli_markdown_rendering.py
@@ -115,3 +115,27 @@ def test_final_assistant_content_can_leave_markdown_raw():
 
     output = _render_to_text(renderable)
     assert "***Bold italic***" in output
+
+
+def test_strip_mode_preserves_intraword_underscores_in_snake_case_identifiers():
+    renderable = _render_final_assistant_content(
+        "Let me look at test_case_with_underscores and SOME_CONST "
+        "then /tmp/snake_case_dir/file_with_name.py",
+        mode="strip",
+    )
+
+    output = _render_to_text(renderable)
+    assert "test_case_with_underscores" in output
+    assert "SOME_CONST" in output
+    assert "snake_case_dir" in output
+    assert "file_with_name" in output
+
+
+def test_strip_mode_still_strips_boundary_underscore_emphasis():
+    renderable = _render_final_assistant_content(
+        "say _hi_ and __bold__ now",
+        mode="strip",
+    )
+
+    output = _render_to_text(renderable)
+    assert "say hi and bold now" in output
diff --git a/ui-tui/src/__tests__/text.test.ts b/ui-tui/src/__tests__/text.test.ts
index 0a11e3cc0..d4a2469e8 100644
--- a/ui-tui/src/__tests__/text.test.ts
+++ b/ui-tui/src/__tests__/text.test.ts
@@ -97,4 +97,12 @@ describe('estimateRows', () => {
 
     expect(estimateRows(md, 40)).toBe(2)
   })
+
+  it('keeps intraword underscores when sizing snake_case identifiers', () => {
+    const w = 80
+    const snake = 'look at test_case_with_underscores now'
+    const plain = 'look at test case with underscores now'
+
+    expect(estimateRows(snake, w)).toBe(estimateRows(plain, w))
+  })
 })
diff --git a/ui-tui/src/lib/text.ts b/ui-tui/src/lib/text.ts
index fb10d7d2d..8541ac3f6 100644
--- a/ui-tui/src/lib/text.ts
+++ b/ui-tui/src/lib/text.ts
@@ -25,9 +25,9 @@ const renderEstimateLine = (line: string) => {
     .replace(/\[(.+?)\]\((https?:\/\/[^\s)]+)\)/g, '$1')
     .replace(/`([^`]+)`/g, '$1')
     .replace(/\*\*(.+?)\*\*/g, '$1')
-    .replace(/__(.+?)__/g, '$1')
+    .replace(/(?<!\w)__(.+?)__(?!\w)/g, '$1')
     .replace(/\*(.+?)\*/g, '$1')
-    .replace(/_(.+?)_/g, '$1')
+    .replace(/(?<!\w)_(.+?)_(?!\w)/g, '$1')
     .replace(/~~(.+?)~~/g, '$1')
     .replace(/==(.+?)==/g, '$1')
     .replace(/\[\^([^\]]+)\]/g, '[$1]')