diff --git a/Content.Tests/DMProject/Tests/Preprocessor/macro_path_double_slash.dm b/Content.Tests/DMProject/Tests/Preprocessor/macro_path_double_slash.dm
new file mode 100644
index 0000000000..6f7976f2a6
--- /dev/null
+++ b/Content.Tests/DMProject/Tests/Preprocessor/macro_path_double_slash.dm
@@ -0,0 +1,47 @@
+//# issue 2649
+
+// A macro that expands to a path can end up pasted directly after a slash, producing an
+// empty path element. BYOND ignores those. This can only happen through macro expansion,
+// since a literal "//" in source is a comment.
+
+#define LEADING /datum/first
+#define MIDDLE /second
+#define TRAILING /first
+
+// "//datum/first"
+/LEADING
+	var/x = 1
+
+// "/datum/first//second"
+/datum/first/MIDDLE
+	var/y = 2
+
+// The shape goonstation's namespace macros expand to, which relies on "##" pasting a
+// leading slash onto a trailing one.
+#define IDENTITY(_ARGS...) ##_ARGS
+#define NS_PATH(_NAME) /datum/namespace/##_NAME
+#define NS_PATH_I(_NAME) /datum/namespace/##_NAME/##IDENTITY
+#define CREATE_NS(a, b) NS_PATH_I(a)(var/##NS_PATH_I(a##__##b)(##b = NS_PATH(a##__##b)))
+#define ADD_TO_NS(a, b) NS_PATH_I(a##__##b)
+
+/datum/namespace
+/datum/namespace/RADIO
+/datum/namespace/RADIO__COL
+
+CREATE_NS(RADIO, COL)
+ADD_TO_NS(RADIO, COL)(var/const/BRIG = "#FF5000")
+
+/proc/RunTest()
+	var/datum/first/F = new
+	ASSERT(F.x == 1)
+
+	var/datum/first/second/S = new
+	ASSERT(S.x == 1)
+	ASSERT(S.y == 2)
+
+	// "/datum//first" in an expression
+	ASSERT(/datum/TRAILING == /datum/first)
+
+	var/datum/namespace/RADIO/N = new
+	ASSERT(N.COL == /datum/namespace/RADIO__COL)
+	ASSERT(/datum/namespace/RADIO__COL::BRIG == "#FF5000")
diff --git a/DMCompiler/Compiler/DM/DMParser.cs b/DMCompiler/Compiler/DM/DMParser.cs
index aefd37901c..d6a3b0b2b3 100644
--- a/DMCompiler/Compiler/DM/DMParser.cs
+++ b/DMCompiler/Compiler/DM/DMParser.cs
@@ -398,12 +398,12 @@ public DMASTFile File() {
                 if (expression) return null;
             }
 
-            string? pathElement = PathElement();
+            string? pathElement = PathElementSkippingEmpty();
             if (pathElement != null) {
                 List<string> pathElements = [pathElement];
                 bool operatorFlag = false;
                 while (pathElement != null && Check(TokenType.DM_Slash)) {
-                    pathElement = PathElement();
+                    pathElement = PathElementSkippingEmpty();
 
                     if (pathElement != null) {
                         if(pathElement == "operator") {
@@ -449,6 +449,32 @@ public DMASTFile File() {
             return null;
         }
 
+        /// <summary>
+        /// Reads the next path element, ignoring any empty ones (the "//" in "/datum//foo").
+        /// BYOND accepts these; they can only come from macro expansion because "//" is a comment in source.
+        /// </summary>
+        /// <returns>The next path element, or null if there isn't one. Slashes read by a failed attempt are given back.</returns>
+        private string? PathElementSkippingEmpty() {
+            string? pathElement = PathElement();
+            if (pathElement != null || Current().Type != TokenType.DM_Slash)
+                return pathElement;
+
+            List<Token> skippedSlashes = new();
+            do {
+                skippedSlashes.Add(Current());
+                Advance();
+
+                pathElement = PathElement();
+                if (pathElement != null)
+                    return pathElement;
+            } while (Current().Type == TokenType.DM_Slash);
+
+            for (int i = skippedSlashes.Count - 1; i >= 0; i--)
+                ReuseToken(skippedSlashes[i]);
+
+            return null;
+        }
+
         /// <summary>
         /// Extracts the text from this token if it is reasonable for it to appear as a typename in a path.
         /// </summary>