diff --git a/exercises/practice/roman-numerals/.meta/tests.toml b/exercises/practice/roman-numerals/.meta/tests.toml
index 521dcc4d..57c6c4be 100644
--- a/exercises/practice/roman-numerals/.meta/tests.toml
+++ b/exercises/practice/roman-numerals/.meta/tests.toml
@@ -1,60 +1,88 @@
-# This is an auto-generated file. Regular comments will be removed when this
-# file is regenerated. Regenerating will not touch any manually added keys,
-# so comments can be added in a "comment" key.
+# This is an auto-generated file.
+#
+# Regenerating this file via `configlet sync` will:
+# - Recreate every `description` key/value pair
+# - Recreate every `reimplements` key/value pair, where they exist in problem-specifications
+# - Remove any `include = true` key/value pair (an omitted `include` key implies inclusion)
+# - Preserve any other key/value pair
+#
+# As user-added comments (using the # character) will be removed when this file
+# is regenerated, comments can be added via a `comment` key.
 
 [19828a3a-fbf7-4661-8ddd-cbaeee0e2178]
-description = "1 is a single I"
+description = "1 is I"
 
 [f088f064-2d35-4476-9a41-f576da3f7b03]
-description = "2 is two I's"
+description = "2 is II"
 
 [b374a79c-3bea-43e6-8db8-1286f79c7106]
-description = "3 is three I's"
+description = "3 is III"
 
 [05a0a1d4-a140-4db1-82e8-fcc21fdb49bb]
-description = "4, being 5 - 1, is IV"
+description = "4 is IV"
 
 [57c0f9ad-5024-46ab-975d-de18c430b290]
-description = "5 is a single V"
+description = "5 is V"
 
 [20a2b47f-e57f-4797-a541-0b3825d7f249]
-description = "6, being 5 + 1, is VI"
+description = "6 is VI"
 
 [ff3fb08c-4917-4aab-9f4e-d663491d083d]
-description = "9, being 10 - 1, is IX"
+description = "9 is IX"
+
+[6d1d82d5-bf3e-48af-9139-87d7165ed509]
+description = "16 is XVI"
 
 [2bda64ca-7d28-4c56-b08d-16ce65716cf6]
-description = "20 is two X's"
+description = "27 is XXVII"
 
 [a1f812ef-84da-4e02-b4f0-89c907d0962c]
-description = "48 is not 50 - 2 but rather 40 + 8"
+description = "48 is XLVIII"
 
 [607ead62-23d6-4c11-a396-ef821e2e5f75]
-description = "49 is not 40 + 5 + 4 but rather 50 - 10 + 10 - 1"
+description = "49 is XLIX"
 
 [d5b283d4-455d-4e68-aacf-add6c4b51915]
-description = "50 is a single L"
+description = "59 is LIX"
+
+[4465ffd5-34dc-44f3-ada5-56f5007b6dad]
+description = "66 is LXVI"
 
 [46b46e5b-24da-4180-bfe2-2ef30b39d0d0]
-description = "90, being 100 - 10, is XC"
+description = "93 is XCIII"
 
 [30494be1-9afb-4f84-9d71-db9df18b55e3]
-description = "100 is a single C"
+description = "141 is CXLI"
 
 [267f0207-3c55-459a-b81d-67cec7a46ed9]
-description = "60, being 50 + 10, is LX"
+description = "163 is CLXIII"
+
+[902ad132-0b4d-40e3-8597-ba5ed611dd8d]
+description = "166 is CLXVI"
 
 [cdb06885-4485-4d71-8bfb-c9d0f496b404]
-description = "400, being 500 - 100, is CD"
+description = "402 is CDII"
 
 [6b71841d-13b2-46b4-ba97-dec28133ea80]
-description = "500 is a single D"
+description = "575 is DLXXV"
+
+[dacb84b9-ea1c-4a61-acbb-ce6b36674906]
+description = "666 is DCLXVI"
 
 [432de891-7fd6-4748-a7f6-156082eeca2f]
-description = "900, being 1000 - 100, is CM"
+description = "911 is CMXI"
 
 [e6de6d24-f668-41c0-88d7-889c0254d173]
-description = "1000 is a single M"
+description = "1024 is MXXIV"
+
+[efbe1d6a-9f98-4eb5-82bc-72753e3ac328]
+description = "1666 is MDCLXVI"
 
 [bb550038-d4eb-4be2-a9ce-f21961ac3bc6]
-description = "3000 is three M's"
+description = "3000 is MMM"
+
+[3bc4b41c-c2e6-49d9-9142-420691504336]
+description = "3001 is MMMI"
+
+[4e18e96b-5fbb-43df-a91b-9cb511fe0856]
+description = "3999 is MMMCMXCIX"
diff --git a/exercises/practice/roman-numerals/src/test/groovy/RomanNumeralsSpec.groovy b/exercises/practice/roman-numerals/src/test/groovy/RomanNumeralsSpec.groovy
index e3e57b32..8075245c 100644
--- a/exercises/practice/roman-numerals/src/test/groovy/RomanNumeralsSpec.groovy
+++ b/exercises/practice/roman-numerals/src/test/groovy/RomanNumeralsSpec.groovy
@@ -19,18 +19,25 @@ class RomanNumeralsSpec extends Specification {
         5      || 'V'
         6      || 'VI'
         9      || 'IX'
+        16     || 'XVI'
         27     || 'XXVII'
         48     || 'XLVIII'
         49     || 'XLIX'
         59     || 'LIX'
+        66     || 'LXVI'
         93     || 'XCIII'
         141    || 'CXLI'
         163    || 'CLXIII'
+        166    || 'CLXVI'
         402    || 'CDII'
         575    || 'DLXXV'
+        666    || 'DCLXVI'
         911    || 'CMXI'
         1024   || 'MXXIV'
+        1666   || 'MDCLXVI'
         3000   || 'MMM'
+        3001   || 'MMMI'
+        3999   || 'MMMCMXCIX'
     }
 
 }