diff --git a/stackvox/text.py b/stackvox/text.py
index e272b29..8cff294 100644
--- a/stackvox/text.py
+++ b/stackvox/text.py
@@ -65,6 +65,7 @@ def strip_emoji(text: str) -> str:
         (r"\s*÷\s*", " divided by "),
         (r"\s*×\s*", " times "),
         (r"\s*=\s*", " equals "),
+        (r"~\s*(?=\d)", "about "),  # ~123 -> "about 123" (else espeak says "tilde 123"); leaves ~/path alone
     ],
 }
 DEFAULT_LOCALE = "en-GB"
@@ -183,6 +184,13 @@ def apply_pronunciations(text: str, mapping: dict[str, str] | None) -> str:
     "postgresql": "postgres",
     "kubectl": "kube control",
     "stackone": "stack one",  # org name espeak garbles as "stac kone"
+    # "dedupe" glued reads as "de-dup" (short u); split + long "dee" gives "dee doop".
+    # Inflections listed explicitly — apply_pronunciations matches whole words only.
+    "dedupe": "dee dupe",
+    "deduped": "dee duped",
+    "deduping": "dee duping",
+    "dedupes": "dee dupes",
+    "dedup": "dee dupe",
 }
 
 
diff --git a/tests/test_text.py b/tests/test_text.py
index 161ca2f..bf6e11c 100644
--- a/tests/test_text.py
+++ b/tests/test_text.py
@@ -113,6 +113,20 @@ def test_math_symbols():
     assert expand_units("770 ÷ 2 × 3 = 5").strip() == "770 divided by 2 times 3 equals 5"
 
 
+def test_tilde_before_number_is_approximately():
+    assert expand_units("~123") == "about 123"
+    assert expand_units("~ 50 items") == "about 50 items"
+
+
+def test_tilde_not_before_number_is_left_alone():
+    # home dir / approx-equal — not an approximated quantity
+    assert expand_units("~/projects") == "~/projects"
+
+
+def test_tilde_approx_end_to_end_with_decimal():
+    assert normalize_for_speech("took ~1.5 hours", markdown=False) == "took about 1 point 5 hours."
+
+
 def test_unknown_locale_falls_back_to_en_gb():
     assert expand_units("£5", locale="xx-YY") == "5 pounds"
 
@@ -306,6 +320,18 @@ def test_dev_terms_leave_correctly_voiced_acronyms_alone():
     assert "API" in out
 
 
+def test_dedupe_respelled_for_speech():
+    assert normalize_for_speech("dedupe the list", markdown=False) == "dee dupe the list."
+    # inflections and case
+    assert "dee duped" in normalize_for_speech("we Deduped it", markdown=False)
+    assert "dee duping" in normalize_for_speech("deduping now", markdown=False)
+
+
+def test_dedupe_does_not_touch_other_words():
+    # whole-word only — must not rewrite the middle of a longer token
+    assert "dee dupe" not in normalize_for_speech("dedupelicated", markdown=False)
+
+
 def test_dev_terms_can_be_disabled():
     assert normalize_for_speech("Use the CLI.", markdown=False, dev_terms=False) == "Use the CLI."