diff --git a/examples/1158-diagnostics-import-dir-file-ambiguous.sx b/examples/1158-diagnostics-import-dir-file-ambiguous.sx
new file mode 100644
index 0000000..0fab5f5
--- /dev/null
+++ b/examples/1158-diagnostics-import-dir-file-ambiguous.sx
@@ -0,0 +1,11 @@
+// An extensionless #import that matches BOTH a `.sx` file and a sibling
+// directory of the same name is ambiguous — the compiler refuses to pick
+// silently and asks for the explicit `.sx` spelling. `modules/std` is the
+// canonical collision: `modules/std.sx` (the prelude) sits next to
+// `modules/std/` (mem/fs/process/...).
+
+#import "modules/std";
+
+main :: () -> s32 {
+    0
+}
diff --git a/examples/expected/1158-diagnostics-import-dir-file-ambiguous.exit b/examples/expected/1158-diagnostics-import-dir-file-ambiguous.exit
new file mode 100644
index 0000000..d00491f
--- /dev/null
+++ b/examples/expected/1158-diagnostics-import-dir-file-ambiguous.exit
@@ -0,0 +1 @@
+1
diff --git a/examples/expected/1158-diagnostics-import-dir-file-ambiguous.stderr b/examples/expected/1158-diagnostics-import-dir-file-ambiguous.stderr
new file mode 100644
index 0000000..d5e4c28
--- /dev/null
+++ b/examples/expected/1158-diagnostics-import-dir-file-ambiguous.stderr
@@ -0,0 +1,5 @@
+error: ambiguous import 'modules/std': both a file 'modules/std.sx' and a directory 'modules/std' exist — write "modules/std.sx" to import the file
+  --> examples/1158-diagnostics-import-dir-file-ambiguous.sx:7:1
+   |
+ 7 | #import "modules/std";
+   | ^^^^^^^^^^^^^^^^^^^^^^
diff --git a/examples/expected/1158-diagnostics-import-dir-file-ambiguous.stdout b/examples/expected/1158-diagnostics-import-dir-file-ambiguous.stdout
new file mode 100644
index 0000000..8b13789
--- /dev/null
+++ b/examples/expected/1158-diagnostics-import-dir-file-ambiguous.stdout
@@ -0,0 +1 @@
+
diff --git a/readme.md b/readme.md
index 7ee85ea..b5d7146 100644
--- a/readme.md
+++ b/readme.md
@@ -398,6 +398,10 @@ Direct C header import:
 math :: #import "modules/math";        // namespaced import (directory: all .sx files merged)
 ```
 
+A path that matches both a file and a same-named sibling directory
+(`modules/std.sx` next to `modules/std/`) is rejected as ambiguous — write the
+`.sx` path to import the file.
+
 When two flat-imported modules each define a function of the same name, every
 module's own code binds its OWN author — a bare call resolves to the same-name
 function in the caller's module (or in its single flat import that provides it).
diff --git a/specs.md b/specs.md
index cdcd45c..c9b5963 100644
--- a/specs.md
+++ b/specs.md
@@ -2495,6 +2495,8 @@ pkg :: #import "modules/math";   // namespaced — all .sx files merged under pk
 
 Directory imports scan only the top level of the specified directory (non-recursive). Files are processed in alphabetical order for deterministic builds. Files within the directory may `#import` each other or external files.
 
+If an extensionless path matches both a file and a sibling directory of the same name (`modules/std.sx` next to `modules/std/`), the import is an error — write the `.sx` path to import the file. Exception: a file importing its own companion directory (`X.sx` importing `X/`) is not ambiguous; the directory is the only sensible target.
+
 Namespaced declarations are accessed with dot notation:
 ```sx
 std.print("hello");
diff --git a/src/imports.zig b/src/imports.zig
index 0ca35a5..eadcb9f 100644
--- a/src/imports.zig
+++ b/src/imports.zig
@@ -1074,7 +1074,32 @@ pub fn resolveImports(
                 try cache.put(resolved_path, result);
                 break :blk result;
             } else |_| {
-                // File read failed — try as directory import
+                // File read failed — try as directory import. An extensionless
+                // path that names a directory next to a same-named `.sx` file
+                // is ambiguous: require the explicit `.sx` spelling for the
+                // file rather than silently picking the directory. Exception:
+                // when the sibling `.sx` is the importing file itself (a test
+                // importing its own companion directory), the directory is the
+                // only sensible target.
+                const sibling_sx = try std.fmt.allocPrint(allocator, "{s}.sx", .{resolved_path});
+                const sibling_exists = if (std.mem.eql(u8, sibling_sx, file_path))
+                    false
+                else if (std.Io.Dir.readFileAlloc(.cwd(), io, sibling_sx, allocator, .limited(10 * 1024 * 1024))) |_|
+                    true
+                else |_|
+                    false;
+                if (sibling_exists) {
+                    const is_dir = if (std.Io.Dir.openDir(.cwd(), io, resolved_path, .{})) |d| dir_blk: {
+                        d.close(io);
+                        break :dir_blk true;
+                    } else |_| false;
+                    if (is_dir) {
+                        if (diagnostics) |diags| {
+                            diags.addFmt(.err, decl.span, "ambiguous import '{s}': both a file '{s}.sx' and a directory '{s}' exist — write \"{s}.sx\" to import the file", .{ imp.path, imp.path, imp.path, imp.path });
+                        }
+                        return error.ImportError;
+                    }
+                }
                 const result = resolveDirectoryImport(allocator, io, resolved_path, chain, cache, source_map, diagnostics, decl.span, stdlib_paths, import_graph, flat_import_graph, comptime_ctx) catch {
                     if (diagnostics) |diags| {
                         diags.addFmt(.err, decl.span, "cannot read import '{s}' (not a file or directory)", .{resolved_path});