diff --git a/tests/ui/parser/deli-ident-issue-1.rs b/tests/ui/parser/deli-ident-issue-1.rs
new file mode 100644
index 00000000000..a8cbf8640f7
--- /dev/null
+++ b/tests/ui/parser/deli-ident-issue-1.rs
@@ -0,0 +1,25 @@
+// error-pattern: this file contains an unclosed delimiter
+#![feature(let_chains)]
+trait Demo {}
+
+impl dyn Demo {
+    pub fn report(&self) -> u32 {
+        let sum = |a: u32,
+                   b: u32,
+                   c: u32| {
+            a + b + c
+        };
+        sum(1, 2, 3)
+    }
+
+    fn check(&self, val: Option<u32>, num: Option<u32>) {
+        if let Some(b) = val
+        && let Some(c) = num {
+        && b == c {
+            //~^ ERROR expected struct
+            //~| ERROR mismatched types
+        }
+    }
+}
+
+fn main() { } //~ ERROR this file contains an unclosed delimiter
diff --git a/tests/ui/parser/deli-ident-issue-1.stderr b/tests/ui/parser/deli-ident-issue-1.stderr
new file mode 100644
index 00000000000..784f598f9d0
--- /dev/null
+++ b/tests/ui/parser/deli-ident-issue-1.stderr
@@ -0,0 +1,37 @@
+error: this file contains an unclosed delimiter
+  --> $DIR/deli-ident-issue-1.rs:25:66
+   |
+LL | impl dyn Demo {
+   |               - unclosed delimiter
+...
+LL |                    c: u32| {
+   |                            - this delimiter might not be properly closed...
+LL |             a + b + c
+LL |         };
+   |         - ...as it matches this but it has different indentation
+...
+LL | fn main() { }
+   |                                                                  ^
+
+error[E0574]: expected struct, variant or union type, found local variable `c`
+  --> $DIR/deli-ident-issue-1.rs:18:17
+   |
+LL |         && b == c {
+   |                 ^ not a struct, variant or union type
+
+error[E0308]: mismatched types
+  --> $DIR/deli-ident-issue-1.rs:18:9
+   |
+LL |       fn check(&self, val: Option<u32>, num: Option<u32>) {
+   |                                                           - expected `()` because of default return type
+...
+LL | /         && b == c {
+LL | |
+LL | |
+LL | |         }
+   | |_________^ expected `()`, found `bool`
+
+error: aborting due to 3 previous errors
+
+Some errors have detailed explanations: E0308, E0574.
+For more information about an error, try `rustc --explain E0308`.
diff --git a/tests/ui/parser/deli-ident-issue-2.rs b/tests/ui/parser/deli-ident-issue-2.rs
new file mode 100644
index 00000000000..5394760df70
--- /dev/null
+++ b/tests/ui/parser/deli-ident-issue-2.rs
@@ -0,0 +1,7 @@
+fn main() {
+    if 1 < 2 {
+        let _a = vec!]; //~ ERROR mismatched closing delimiter
+    }
+} //~ ERROR unexpected closing delimiter
+
+fn main() {}
diff --git a/tests/ui/parser/deli-ident-issue-2.stderr b/tests/ui/parser/deli-ident-issue-2.stderr
new file mode 100644
index 00000000000..782dac8f32d
--- /dev/null
+++ b/tests/ui/parser/deli-ident-issue-2.stderr
@@ -0,0 +1,21 @@
+error: unexpected closing delimiter: `}`
+  --> $DIR/deli-ident-issue-2.rs:5:1
+   |
+LL | fn main() {
+   |           - this opening brace...
+...
+LL |     }
+   |     - ...matches this closing brace
+LL | }
+   | ^ unexpected closing delimiter
+
+error: mismatched closing delimiter: `]`
+  --> $DIR/deli-ident-issue-2.rs:2:14
+   |
+LL |     if 1 < 2 {
+   |              ^ unclosed delimiter
+LL |         let _a = vec!];
+   |                      ^ mismatched closing delimiter
+
+error: aborting due to 2 previous errors
+
diff --git a/tests/ui/parser/issue-68987-unmatch-issue-1.rs b/tests/ui/parser/issue-68987-unmatch-issue-1.rs
new file mode 100644
index 00000000000..30e7ef46736
--- /dev/null
+++ b/tests/ui/parser/issue-68987-unmatch-issue-1.rs
@@ -0,0 +1,12 @@
+// This file has unexpected closing delimiter,
+
+fn func(o: Option<u32>) {
+    match o {
+        Some(_x) => {}   // Extra '}'
+            let _ = if true {};
+        }
+        None => {}
+    }
+} //~ ERROR unexpected closing delimiter
+
+fn main() {}
diff --git a/tests/ui/parser/issue-68987-unmatch-issue-1.stderr b/tests/ui/parser/issue-68987-unmatch-issue-1.stderr
new file mode 100644
index 00000000000..b5c1887f76f
--- /dev/null
+++ b/tests/ui/parser/issue-68987-unmatch-issue-1.stderr
@@ -0,0 +1,11 @@
+error: unexpected closing delimiter: `}`
+  --> $DIR/issue-68987-unmatch-issue-1.rs:10:1
+   |
+LL |         None => {}
+   |                 -- block is empty, you might have not meant to close it
+LL |     }
+LL | }
+   | ^ unexpected closing delimiter
+
+error: aborting due to previous error
+
diff --git a/tests/ui/parser/issue-68987-unmatch-issue-2.rs b/tests/ui/parser/issue-68987-unmatch-issue-2.rs
new file mode 100644
index 00000000000..89aaa68ba40
--- /dev/null
+++ b/tests/ui/parser/issue-68987-unmatch-issue-2.rs
@@ -0,0 +1,14 @@
+// FIXME: this case need more work to fix
+// currently the TokenTree matching ')' with '{', which is not user friendly for diagnostics
+async fn obstest() -> Result<> {
+    let obs_connect = || -> Result<(), MyError) { //~ ERROR mismatched closing delimiter
+        async {
+        }
+    }
+
+    if let Ok(version, scene_list) = obs_connect() {
+
+    } else {
+
+    }
+} //~ ERROR unexpected closing delimiter
diff --git a/tests/ui/parser/issue-68987-unmatch-issue-2.stderr b/tests/ui/parser/issue-68987-unmatch-issue-2.stderr
new file mode 100644
index 00000000000..253f12d44b8
--- /dev/null
+++ b/tests/ui/parser/issue-68987-unmatch-issue-2.stderr
@@ -0,0 +1,21 @@
+error: unexpected closing delimiter: `}`
+  --> $DIR/issue-68987-unmatch-issue-2.rs:14:1
+   |
+LL |     } else {
+   |            - this opening brace...
+LL |
+LL |     }
+   |     - ...matches this closing brace
+LL | }
+   | ^ unexpected closing delimiter
+
+error: mismatched closing delimiter: `)`
+  --> $DIR/issue-68987-unmatch-issue-2.rs:3:32
+   |
+LL | async fn obstest() -> Result<> {
+   |                                ^ unclosed delimiter
+LL |     let obs_connect = || -> Result<(), MyError) {
+   |                                               ^ mismatched closing delimiter
+
+error: aborting due to 2 previous errors
+
diff --git a/tests/ui/parser/issue-68987-unmatch-issue-3.rs b/tests/ui/parser/issue-68987-unmatch-issue-3.rs
new file mode 100644
index 00000000000..e98df8d7c3c
--- /dev/null
+++ b/tests/ui/parser/issue-68987-unmatch-issue-3.rs
@@ -0,0 +1,8 @@
+// the `{` is closed with `)`, there is a missing `(`
+fn f(i: u32, j: u32) {
+    let res = String::new();
+    let mut cnt = i;
+    while cnt < j {
+        write!&mut res, " "); //~ ERROR mismatched closing delimiter
+    }
+} //~ ERROR unexpected closing delimiter
diff --git a/tests/ui/parser/issue-68987-unmatch-issue-3.stderr b/tests/ui/parser/issue-68987-unmatch-issue-3.stderr
new file mode 100644
index 00000000000..258a692c855
--- /dev/null
+++ b/tests/ui/parser/issue-68987-unmatch-issue-3.stderr
@@ -0,0 +1,21 @@
+error: unexpected closing delimiter: `}`
+  --> $DIR/issue-68987-unmatch-issue-3.rs:8:1
+   |
+LL | fn f(i: u32, j: u32) {
+   |                      - this opening brace...
+...
+LL |     }
+   |     - ...matches this closing brace
+LL | }
+   | ^ unexpected closing delimiter
+
+error: mismatched closing delimiter: `)`
+  --> $DIR/issue-68987-unmatch-issue-3.rs:5:19
+   |
+LL |     while cnt < j {
+   |                   ^ unclosed delimiter
+LL |         write!&mut res, " ");
+   |                            ^ mismatched closing delimiter
+
+error: aborting due to 2 previous errors
+
diff --git a/tests/ui/parser/issue-68987-unmatch-issue.rs b/tests/ui/parser/issue-68987-unmatch-issue.rs
new file mode 100644
index 00000000000..5a3620bf24b
--- /dev/null
+++ b/tests/ui/parser/issue-68987-unmatch-issue.rs
@@ -0,0 +1,12 @@
+// This file has unexpected closing delimiter,
+
+fn func(o: Option<u32>) {
+    match o {
+        Some(_x) =>   // Missing '{'
+            let _ = if true {};
+        }
+        None => {}
+    }
+} //~ ERROR unexpected closing delimiter
+
+fn main() {}
diff --git a/tests/ui/parser/issue-68987-unmatch-issue.stderr b/tests/ui/parser/issue-68987-unmatch-issue.stderr
new file mode 100644
index 00000000000..00e9c9a5cce
--- /dev/null
+++ b/tests/ui/parser/issue-68987-unmatch-issue.stderr
@@ -0,0 +1,11 @@
+error: unexpected closing delimiter: `}`
+  --> $DIR/issue-68987-unmatch-issue.rs:10:1
+   |
+LL |         None => {}
+   |                 -- block is empty, you might have not meant to close it
+LL |     }
+LL | }
+   | ^ unexpected closing delimiter
+
+error: aborting due to previous error
+
diff --git a/tests/ui/parser/issues/issue-69259.rs b/tests/ui/parser/issues/issue-69259.rs
new file mode 100644
index 00000000000..01fc2c08546
--- /dev/null
+++ b/tests/ui/parser/issues/issue-69259.rs
@@ -0,0 +1,3 @@
+fn main() {}
+
+fn f) {} //~ ERROR unexpected closing delimiter
diff --git a/tests/ui/parser/issues/issue-69259.stderr b/tests/ui/parser/issues/issue-69259.stderr
new file mode 100644
index 00000000000..f4cb391cb1f
--- /dev/null
+++ b/tests/ui/parser/issues/issue-69259.stderr
@@ -0,0 +1,13 @@
+error: unexpected closing delimiter: `)`
+  --> $DIR/issue-69259.rs:3:5
+   |
+LL | fn main() {}
+   |           -- ...matches this closing brace
+   |           |
+   |           this opening brace...
+LL |
+LL | fn f) {}
+   |     ^ unexpected closing delimiter
+
+error: aborting due to previous error
+