diff --git a/src/bootstrap/test.rs b/src/bootstrap/test.rs
index 86d940cd733da..62c458fe81770 100644
--- a/src/bootstrap/test.rs
+++ b/src/bootstrap/test.rs
@@ -734,9 +734,24 @@ impl Step for RustdocGUI {
             }
 
             let out_dir = builder.test_out(self.target).join("rustdoc-gui");
-            let mut command = builder.rustdoc_cmd(self.compiler);
-            command.arg("src/test/rustdoc-gui/lib.rs").arg("-o").arg(&out_dir);
-            builder.run(&mut command);
+
+            for file in fs::read_dir("src/test/rustdoc-gui").unwrap() {
+                let file = file.unwrap();
+                let file_name = file.file_name();
+
+                if !file_name.to_str().unwrap().ends_with(".rs") {
+                    continue;
+                }
+
+                let mut command = builder.rustdoc_cmd(self.compiler);
+                command
+                    .arg(&Path::new("src/test/rustdoc-gui").join(file_name))
+                    .arg("-o")
+                    .arg(&out_dir)
+                    .arg("-Zunstable-options")
+                    .arg("--generate-case-insensitive");
+                builder.run(&mut command);
+            }
 
             for file in fs::read_dir("src/test/rustdoc-gui").unwrap() {
                 let file = file.unwrap();
@@ -750,7 +765,7 @@ impl Step for RustdocGUI {
                 command
                     .arg("src/tools/rustdoc-gui/tester.js")
                     .arg("--doc-folder")
-                    .arg(out_dir.join("test_docs"))
+                    .arg(&out_dir)
                     .arg("--test-file")
                     .arg(file_path);
                 builder.run(&mut command);
diff --git a/src/test/rustdoc-gui/basic-code.goml b/src/test/rustdoc-gui/basic-code.goml
index 8da465662547a..d014ed60eb039 100644
--- a/src/test/rustdoc-gui/basic-code.goml
+++ b/src/test/rustdoc-gui/basic-code.goml
@@ -1,3 +1,3 @@
-goto: file://|DOC_PATH|/index.html
+goto: file://|DOC_PATH|/test_docs/index.html
 click: ".srclink"
 assert: (".line-numbers", 1)
diff --git a/src/test/rustdoc-gui/basic.goml b/src/test/rustdoc-gui/basic.goml
index ed23300860b70..44fcec3393744 100644
--- a/src/test/rustdoc-gui/basic.goml
+++ b/src/test/rustdoc-gui/basic.goml
@@ -1,4 +1,4 @@
-goto: file://|DOC_PATH|/index.html
+goto: file://|DOC_PATH|/test_docs/index.html
 assert: ("#functions")
 goto: ./struct.Foo.html
 assert: ("div.type-decl")
diff --git a/src/test/rustdoc-gui/check_info_sign_position.goml b/src/test/rustdoc-gui/check_info_sign_position.goml
index 9aa72a3ad53e7..d64ee0261370c 100644
--- a/src/test/rustdoc-gui/check_info_sign_position.goml
+++ b/src/test/rustdoc-gui/check_info_sign_position.goml
@@ -1,4 +1,4 @@
-goto: file://|DOC_PATH|/index.html
+goto: file://|DOC_PATH|/test_docs/index.html
 goto: ./fn.check_list_code_block.html
 // If the codeblock is the first element of the docblock, the information tooltip must have
 // have some top margin to avoid going over the toggle (the "[+]").
diff --git a/src/test/rustdoc-gui/code-sidebar-toggle.goml b/src/test/rustdoc-gui/code-sidebar-toggle.goml
index 69fc860244b7b..7e7003d4340a3 100644
--- a/src/test/rustdoc-gui/code-sidebar-toggle.goml
+++ b/src/test/rustdoc-gui/code-sidebar-toggle.goml
@@ -1,4 +1,4 @@
-goto: file://|DOC_PATH|/index.html
+goto: file://|DOC_PATH|/test_docs/index.html
 click: ".srclink"
 click: "#sidebar-toggle"
 wait-for: 500
diff --git a/src/test/rustdoc-gui/insensitive-case-check.goml b/src/test/rustdoc-gui/insensitive-case-check.goml
new file mode 100644
index 0000000000000..d25fbfac70b7b
--- /dev/null
+++ b/src/test/rustdoc-gui/insensitive-case-check.goml
@@ -0,0 +1,7 @@
+goto: file://|DOC_PATH|/insensitive_case_docs/struct.ab.html
+// Checks that the sidebar was filled.
+wait-for: ".sidebar-elems > .items > .sidebar-title"
+// Checks that the content has been loaded
+assert: ".impl-items > h4"
+// Checks that the collapse toggles have been generated as expected
+assert: ".impl-items > h4 > .collapse-toggle"
diff --git a/src/test/rustdoc-gui/insensitive-test.rs b/src/test/rustdoc-gui/insensitive-test.rs
new file mode 100644
index 0000000000000..6f63c32127a51
--- /dev/null
+++ b/src/test/rustdoc-gui/insensitive-test.rs
@@ -0,0 +1,19 @@
+//! The point of this crate is to test the insensitive case handling.
+
+#![crate_name = "insensitive_case_docs"]
+
+#![allow(non_camel_case_types)]
+
+/// This is ab.
+pub struct ab;
+
+impl ab {
+    pub fn foo(&self) {}
+}
+
+/// This is another Ab!
+pub struct Ab;
+
+impl Ab {
+    pub fn bar(&self) {}
+}
diff --git a/src/test/rustdoc-gui/list_code_block.goml b/src/test/rustdoc-gui/list_code_block.goml
index 6f2465a5587f2..7d3490e9d9410 100644
--- a/src/test/rustdoc-gui/list_code_block.goml
+++ b/src/test/rustdoc-gui/list_code_block.goml
@@ -1,3 +1,3 @@
-goto: file://|DOC_PATH|/index.html
+goto: file://|DOC_PATH|/test_docs/index.html
 goto: ./fn.check_list_code_block.html
 assert: ("pre.rust.fn")
diff --git a/src/test/rustdoc-gui/nojs-attr-pos.goml b/src/test/rustdoc-gui/nojs-attr-pos.goml
index 35daa4cb9e322..0e87c93ab3b32 100644
--- a/src/test/rustdoc-gui/nojs-attr-pos.goml
+++ b/src/test/rustdoc-gui/nojs-attr-pos.goml
@@ -1,5 +1,5 @@
 // Check that the attributes are well positioned when javascript is disabled (since
 // there is no toggle to display)
 javascript: false
-goto: file://|DOC_PATH|/struct.Foo.html
+goto: file://|DOC_PATH|/test_docs/struct.Foo.html
 assert: (".attributes", {"margin-left": "0px"})
diff --git a/src/test/rustdoc-gui/search-input-mobile.goml b/src/test/rustdoc-gui/search-input-mobile.goml
index 3eec3459a6393..5c95db70aecdd 100644
--- a/src/test/rustdoc-gui/search-input-mobile.goml
+++ b/src/test/rustdoc-gui/search-input-mobile.goml
@@ -1,6 +1,6 @@
 // Test to ensure that you can click on the search input, whatever the width.
 // The PR which fixed it is: https://github.com/rust-lang/rust/pull/81592
-goto: file://|DOC_PATH|/index.html
+goto: file://|DOC_PATH|/test_docs/index.html
 size: (463, 700)
 // We first check that the search input isn't already focused.
 assert-false: ("input.search-input:focus")
diff --git a/src/test/rustdoc-gui/shortcuts.goml b/src/test/rustdoc-gui/shortcuts.goml
index c35b48f57f4d2..884c38d85fbdb 100644
--- a/src/test/rustdoc-gui/shortcuts.goml
+++ b/src/test/rustdoc-gui/shortcuts.goml
@@ -1,5 +1,5 @@
 // Check that the various shortcuts are working.
-goto: file://|DOC_PATH|/index.html
+goto: file://|DOC_PATH|/test_docs/index.html
 // We first check that the search input isn't already focused.
 assert-false: "input.search-input:focus"
 press-key: "s"
diff --git a/src/test/rustdoc-gui/theme-change.goml b/src/test/rustdoc-gui/theme-change.goml
index 5bd65f61f4905..bc9063edd1e7a 100644
--- a/src/test/rustdoc-gui/theme-change.goml
+++ b/src/test/rustdoc-gui/theme-change.goml
@@ -1,4 +1,4 @@
-goto: file://|DOC_PATH|/index.html
+goto: file://|DOC_PATH|/test_docs/index.html
 click: "#theme-picker"
 click: "#theme-choices > button:first-child"
 wait-for: 500
diff --git a/src/test/rustdoc-gui/toggle-docs.goml b/src/test/rustdoc-gui/toggle-docs.goml
index 1ded33f659d3c..93bdf41a6a09e 100644
--- a/src/test/rustdoc-gui/toggle-docs.goml
+++ b/src/test/rustdoc-gui/toggle-docs.goml
@@ -1,4 +1,4 @@
-goto: file://|DOC_PATH|/index.html
+goto: file://|DOC_PATH|/test_docs/index.html
 click: "#toggle-all-docs"
 wait-for: 5000
 assert: ("#main > div.docblock.hidden-by-usual-hider")
diff --git a/src/test/rustdoc-gui/trait-sidebar-item-order.goml b/src/test/rustdoc-gui/trait-sidebar-item-order.goml
index 914486e1c281d..2e9f85336ecd8 100644
--- a/src/test/rustdoc-gui/trait-sidebar-item-order.goml
+++ b/src/test/rustdoc-gui/trait-sidebar-item-order.goml
@@ -1,4 +1,4 @@
-goto: file://|DOC_PATH|/trait.AnotherOne.html
+goto: file://|DOC_PATH|/test_docs/trait.AnotherOne.html
 assert: (".sidebar-links a:nth-of-type(1)", "another")
 assert: (".sidebar-links a:nth-of-type(2)", "func1")
 assert: (".sidebar-links a:nth-of-type(3)", "func2")
diff --git a/src/test/rustdoc/insensitive-case.rs b/src/test/rustdoc/insensitive-case.rs
new file mode 100644
index 0000000000000..a64e794adcf01
--- /dev/null
+++ b/src/test/rustdoc/insensitive-case.rs
@@ -0,0 +1,18 @@
+// compile-flags: -Zunstable-options --generate-case-insensitive
+
+#![crate_name = "foo"]
+
+// @!has 'foo/struct.Aa.html'
+// @has 'foo/struct.aa.html'
+// @!has 'foo/struct.aa.html' '//h4[@id="method.new"]'
+pub struct aa;
+
+impl aa {
+   pub fn foo(&self) {}
+}
+
+pub struct Aa;
+
+impl Aa {
+   pub fn foo(&self) {}
+}