diff --git a/Content.IntegrationTests/Tests/PostMapInitTest.cs b/Content.IntegrationTests/Tests/PostMapInitTest.cs
index 22db3ca31f..87c996452e 100644
--- a/Content.IntegrationTests/Tests/PostMapInitTest.cs
+++ b/Content.IntegrationTests/Tests/PostMapInitTest.cs
@@ -1,6 +1,7 @@
 using System.Collections.Generic;
 using System.IO;
 using System.Linq;
+using System.Text.RegularExpressions;
 using Content.Server.Administration.Systems;
 using Content.Server.GameTicking;
 using Content.Server.Maps;
@@ -44,17 +45,43 @@ namespace Content.IntegrationTests.Tests
             AdminTestArenaSystem.ArenaMapPath
         };
 
+        /// <summary>
+        /// A dictionary linking maps to collections of entity prototype ids that should be exempt from "DoNotMap" restrictions.
+        /// </summary>
+        /// <remarks>
+        /// This declares that the listed entity prototypes are allowed to be present on the map
+        /// despite being categorized as "DoNotMap", while any unlisted prototypes will still
+        /// cause the test to fail.
+        /// </remarks>
+        private static readonly Dictionary<string, HashSet<EntProtoId>> DoNotMapWhitelistSpecific = new()
+        {
+            {"/Maps/bagel.yml", ["RubberStampMime"]},
+            {"/Maps/reach.yml", ["HandheldCrewMonitor"]},
+            {"/Maps/Shuttles/ShuttleEvent/honki.yml", ["GoldenBikeHorn", "RubberStampClown"]},
+            {"/Maps/Shuttles/ShuttleEvent/syndie_evacpod.yml", ["RubberStampSyndicate"]},
+            {"/Maps/Shuttles/ShuttleEvent/cruiser.yml", ["ShuttleGunPerforator"]},
+            {"/Maps/Shuttles/ShuttleEvent/instigator.yml", ["ShuttleGunFriendship"]},
+        };
+
+        /// <summary>
+        /// Maps listed here are given blanket freedom to contain "DoNotMap" entities. Use sparingly.
+        /// </summary>
+        /// <remarks>
+        /// It is also possible to whitelist entire directories here. For example, adding
+        /// "/Maps/Shuttles/**" will whitelist all shuttle maps.
+        /// </remarks>
         private static readonly string[] DoNotMapWhitelist =
         {
             "/Maps/centcomm.yml",
-            "/Maps/bagel.yml", // Contains mime's rubber stamp --> Either fix this, remove the category, or remove this comment if intentional.
-            "/Maps/reach.yml", // Contains handheld crew monitor
-            "/Maps/Shuttles/ShuttleEvent/cruiser.yml", // Contains LSE-1200c "Perforator"
-            "/Maps/Shuttles/ShuttleEvent/honki.yml", // Contains golden honker, clown's rubber stamp
-            "/Maps/Shuttles/ShuttleEvent/instigator.yml", // Contains EXP-320g "Friendship"
-            "/Maps/Shuttles/ShuttleEvent/syndie_evacpod.yml", // Contains syndicate rubber stamp
         };
 
+        /// <summary>
+        /// Converts the above globs into regex so your eyes dont bleed trying to add filepaths.
+        /// </summary>
+        private static readonly Regex[] DoNotMapWhiteListRegexes = DoNotMapWhitelist
+            .Select(glob => new Regex(GlobToRegex(glob), RegexOptions.IgnoreCase | RegexOptions.Compiled))
+            .ToArray();
+
         private static readonly string[] GameMaps =
         {
             "Dev",
@@ -247,17 +274,30 @@ namespace Content.IntegrationTests.Tests
             await pair.CleanReturnAsync();
         }
 
+        private bool IsWhitelistedForMap(EntProtoId protoId, ResPath map)
+        {
+            if (!DoNotMapWhitelistSpecific.TryGetValue(map.ToString(), out var allowedProtos))
+                return false;
+
+            return allowedProtos.Contains(protoId);
+        }
+
         /// <summary>
         /// Check that maps do not have any entities that belong to the DoNotMap entity category
         /// </summary>
         private void CheckDoNotMap(ResPath map, YamlNode node, IPrototypeManager protoManager)
         {
-            if (DoNotMapWhitelist.Contains(map.ToString()))
-                return;
+            foreach (var regex in DoNotMapWhiteListRegexes)
+            {
+                if (regex.IsMatch(map.ToString()))
+                    return;
+            }
 
             var yamlEntities = node["entities"];
             var dnmCategory = protoManager.Index(DoNotMapCategory);
 
+            // Make a set containing all the specific whitelisted proto ids for this map
+            HashSet<EntProtoId> unusedExemptions = DoNotMapWhitelistSpecific.TryGetValue(map.ToString(), out var exemptions) ? new(exemptions) : [];
             Assert.Multiple(() =>
             {
                 foreach (var yamlEntity in (YamlSequenceNode)yamlEntities)
@@ -268,10 +308,17 @@ namespace Content.IntegrationTests.Tests
                     if (!protoManager.TryIndex(protoId, out var proto))
                         continue;
 
-                    Assert.That(!proto.Categories.Contains(dnmCategory),
+                    Assert.That(!proto.Categories.Contains(dnmCategory) || IsWhitelistedForMap(protoId, map),
                         $"\nMap {map} contains entities in the DO NOT MAP category ({proto.Name})");
+
+                    // The proto id is used on this map, so remove it from the set
+                    unusedExemptions.Remove(protoId);
                 }
             });
+
+            // If there are any proto ids left, they must not have been used in the map!
+            Assert.That(unusedExemptions, Is.Empty,
+                $"Map {map} has DO NOT MAP entities whitelisted that are not present in the map: {string.Join(", ", unusedExemptions)}");
         }
 
         private bool IsPreInit(ResPath map,
@@ -332,7 +379,7 @@ namespace Content.IntegrationTests.Tests
                 MapId mapId;
                 try
                 {
-                    var opts = DeserializationOptions.Default with {InitializeMaps = true};
+                    var opts = DeserializationOptions.Default with { InitializeMaps = true };
                     ticker.LoadGameMap(protoManager.Index<GameMapPrototype>(mapProto), out mapId, opts);
                 }
                 catch (Exception ex)
@@ -439,7 +486,7 @@ namespace Content.IntegrationTests.Tests
 #nullable enable
             while (queryPoint.MoveNext(out T? comp, out var xform))
             {
-                var spawner = (ISpawnPoint) comp;
+                var spawner = (ISpawnPoint)comp;
 
                 if (spawner.SpawnType is not SpawnPointType.LateJoin
                 || xform.GridUid == null
@@ -553,5 +600,20 @@ namespace Content.IntegrationTests.Tests
             await server.WaitRunTicks(1);
             await pair.CleanReturnAsync();
         }
+
+        /// <summary>
+        /// Lets us the convert the filepaths to regex without eyeglaze trying to add new paths.
+        /// </summary>
+        private static string GlobToRegex(string glob)
+        {
+            var regex = Regex.Escape(glob)
+                .Replace(@"\*\*", "**") // replace **
+                .Replace(@"\*", "*")    // replace *
+                .Replace("**", ".*")    // ** → match across folders
+                .Replace("*", @"[^/]*") // * → match within a single folder
+                .Replace(@"\?", ".");   // ? → any single character
+
+            return $"^{regex}$";
+        }
     }
 }