diff --git a/compiler/rustc_parse/src/parser/diagnostics.rs b/compiler/rustc_parse/src/parser/diagnostics.rs
index 1ea01d95a134e..6bdd6ece1fd37 100644
--- a/compiler/rustc_parse/src/parser/diagnostics.rs
+++ b/compiler/rustc_parse/src/parser/diagnostics.rs
@@ -235,6 +235,12 @@ impl<'a> Parser<'a> {
             })
         }
 
+        let prev_token_to_string = pprust::token_kind_to_string(&self.prev_token.kind);
+        let prev_token_seems_reserved_token = !self.prev_token.is_path_segment_keyword()
+            && self.prev_token.is_ident()
+            && Ident::from_str(&prev_token_to_string.to_lowercase()).is_reserved()
+            && prev_token_to_string != prev_token_to_string.to_lowercase();
+
         let mut expected = edible
             .iter()
             .map(|x| TokenType::Token(x.clone()))
@@ -246,15 +252,28 @@ impl<'a> Parser<'a> {
         let expect = tokens_to_string(&expected[..]);
         let actual = super::token_descr(&self.token);
         let (msg_exp, (label_sp, label_exp)) = if expected.len() > 1 {
-            let short_expect = if expected.len() > 6 {
-                format!("{} possible tokens", expected.len())
+            if prev_token_seems_reserved_token {
+                (
+                    format!("`{:?}` is not a keyword", prev_token_to_string),
+                    (
+                        self.prev_token.span,
+                        format!("try `{:?}` instead", prev_token_to_string.to_lowercase()),
+                    ),
+                )
             } else {
-                expect.clone()
-            };
-            (
-                format!("expected one of {}, found {}", expect, actual),
-                (self.prev_token.span.shrink_to_hi(), format!("expected one of {}", short_expect)),
-            )
+                let short_expect = if expected.len() > 6 {
+                    format!("{} possible tokens", expected.len())
+                } else {
+                    expect.clone()
+                };
+                (
+                    format!("expected one of {}, found {}", expect, actual),
+                    (
+                        self.prev_token.span.shrink_to_hi(),
+                        format!("expected one of {}", short_expect),
+                    ),
+                )
+            }
         } else if expected.is_empty() {
             (
                 format!("unexpected token: {}", actual),
@@ -267,13 +286,19 @@ impl<'a> Parser<'a> {
             )
         };
         self.last_unexpected_token_span = Some(self.token.span);
-        let mut err = self.struct_span_err(self.token.span, &msg_exp);
+        let mut err = if !prev_token_seems_reserved_token {
+            self.struct_span_err(self.token.span, &msg_exp)
+        } else {
+            self.struct_span_err(self.prev_token.span, &msg_exp)
+        };
+
         let sp = if self.token == token::Eof {
             // This is EOF; don't want to point at the following char, but rather the last token.
             self.prev_token.span
         } else {
             label_sp
         };
+
         match self.recover_closing_delimiter(
             &expected
                 .iter()
@@ -295,7 +320,9 @@ impl<'a> Parser<'a> {
         }
 
         let sm = self.sess.source_map();
-        if self.prev_token.span == DUMMY_SP {
+        if prev_token_seems_reserved_token {
+            err.span_label(self.prev_token.span, label_exp);
+        } else if self.prev_token.span == DUMMY_SP {
             // Account for macro context where the previous span might not be
             // available to avoid incorrect output (#54841).
             err.span_label(self.token.span, label_exp);
diff --git a/src/test/ui/parser/mistyped_reserved_token.rs b/src/test/ui/parser/mistyped_reserved_token.rs
new file mode 100644
index 0000000000000..9d463fa26ca14
--- /dev/null
+++ b/src/test/ui/parser/mistyped_reserved_token.rs
@@ -0,0 +1,5 @@
+fn main() {
+    let a = While true { //~ ERROR
+        break;
+    };
+}
diff --git a/src/test/ui/parser/mistyped_reserved_token.stderr b/src/test/ui/parser/mistyped_reserved_token.stderr
new file mode 100644
index 0000000000000..d6f76f98b5038
--- /dev/null
+++ b/src/test/ui/parser/mistyped_reserved_token.stderr
@@ -0,0 +1,8 @@
+error: `"While"` is not a keyword
+  --> $DIR/mistyped_reserved_token.rs:2:13
+   |
+LL |     let a = While true {
+   |             ^^^^^ try `"while"` instead
+
+error: aborting due to previous error
+