diff --git a/compiler/rustc_parse/src/parser/expr.rs b/compiler/rustc_parse/src/parser/expr.rs
index df865d77b9bb4..8d7470e252797 100644
--- a/compiler/rustc_parse/src/parser/expr.rs
+++ b/compiler/rustc_parse/src/parser/expr.rs
@@ -2480,7 +2480,7 @@ impl<'a> Parser<'a> {
             )?;
             let guard = if this.eat_keyword(kw::If) {
                 let if_span = this.prev_token.span;
-                let cond = this.parse_expr()?;
+                let cond = this.parse_match_guard_cond()?;
                 let (has_let_expr, does_not_have_bin_op) = check_let_expr(&cond);
                 if has_let_expr {
                     if does_not_have_bin_op {
@@ -2496,6 +2496,15 @@ impl<'a> Parser<'a> {
             };
             let arrow_span = this.token.span;
             if let Err(mut err) = this.expect(&token::FatArrow) {
+                if guard.is_some() && this.token.kind == token::OpenDelim(token::Brace) {
+                    err.span_suggestion_verbose(
+                        this.token.span.shrink_to_lo(),
+                        "try adding a fat arrow here",
+                        "=> ".to_string(),
+                        Applicability::MaybeIncorrect,
+                    );
+                    err.emit();
+                }
                 // We might have a `=>` -> `=` or `->` typo (issue #89396).
                 if TokenKind::FatArrow
                     .similar_tokens()
@@ -2617,6 +2626,26 @@ impl<'a> Parser<'a> {
         }
     }
 
+    fn parse_match_guard_cond(&mut self) -> PResult<'a, P<Expr>> {
+        let snapshot = self.clone();
+        let mut cond = self.parse_expr()?;
+        let (is_lhs_struct, is_rhs_struct) = match cond.kind {
+            ExprKind::Binary(_, ref lhs, ref rhs) => {
+                (matches!(lhs.kind, ExprKind::Struct(..)), matches!(rhs.kind, ExprKind::Struct(..)))
+            }
+            _ => (false, false),
+        };
+        if !is_lhs_struct
+            && (!is_rhs_struct
+                || is_rhs_struct && self.token.kind != token::OpenDelim(token::Brace))
+            && self.token.kind != token::FatArrow
+        {
+            *self = snapshot;
+            cond = self.parse_cond_expr()?;
+        }
+        Ok(cond)
+    }
+
     fn is_do_catch_block(&self) -> bool {
         self.token.is_keyword(kw::Do)
             && self.is_keyword_ahead(1, &[kw::Catch])
diff --git a/src/test/ui/parser/issues/issue-15980.rs b/src/test/ui/parser/issues/issue-15980.rs
index 87faa7d5ff1bf..ccd4881ccd3bd 100644
--- a/src/test/ui/parser/issues/issue-15980.rs
+++ b/src/test/ui/parser/issues/issue-15980.rs
@@ -5,13 +5,12 @@ fn main(){
     match x {
         Err(ref e) if e.kind == io::EndOfFile {
             //~^ NOTE while parsing this struct
+            //~| ERROR expected one of `!`, `.`, `::`, `=>`, `?`, or an operator, found `{`
+            //~| NOTE expected one of `!`, `.`, `::`, `=>`, `?`, or an operator
             return
             //~^ ERROR expected identifier, found keyword `return`
             //~| NOTE expected identifier, found keyword
         }
-        //~^ NOTE expected one of `.`, `=>`, `?`, or an operator
         _ => {}
-        //~^ ERROR expected one of `.`, `=>`, `?`, or an operator, found reserved identifier `_`
-        //~| NOTE unexpected token
     }
 }
diff --git a/src/test/ui/parser/issues/issue-15980.stderr b/src/test/ui/parser/issues/issue-15980.stderr
index c59c811199ea8..67fb2d5edd613 100644
--- a/src/test/ui/parser/issues/issue-15980.stderr
+++ b/src/test/ui/parser/issues/issue-15980.stderr
@@ -1,9 +1,9 @@
 error: expected identifier, found keyword `return`
-  --> $DIR/issue-15980.rs:8:13
+  --> $DIR/issue-15980.rs:10:13
    |
 LL |         Err(ref e) if e.kind == io::EndOfFile {
    |                                 ------------- while parsing this struct
-LL |
+...
 LL |             return
    |             ^^^^^^ expected identifier, found keyword
    |
@@ -12,14 +12,16 @@ help: escape `return` to use it as an identifier
 LL |             r#return
    |             ++
 
-error: expected one of `.`, `=>`, `?`, or an operator, found reserved identifier `_`
-  --> $DIR/issue-15980.rs:13:9
+error: expected one of `!`, `.`, `::`, `=>`, `?`, or an operator, found `{`
+  --> $DIR/issue-15980.rs:6:47
    |
-LL |         }
-   |          - expected one of `.`, `=>`, `?`, or an operator
-LL |
-LL |         _ => {}
-   |         ^ unexpected token
+LL |         Err(ref e) if e.kind == io::EndOfFile {
+   |                                               ^ expected one of `!`, `.`, `::`, `=>`, `?`, or an operator
+   |
+help: try adding a fat arrow here
+   |
+LL |         Err(ref e) if e.kind == io::EndOfFile => {
+   |                                               ++
 
 error: aborting due to 2 previous errors
 
diff --git a/src/test/ui/parser/missing-fat-arrow-after-match-guard.rs b/src/test/ui/parser/missing-fat-arrow-after-match-guard.rs
new file mode 100644
index 0000000000000..284680ebbea75
--- /dev/null
+++ b/src/test/ui/parser/missing-fat-arrow-after-match-guard.rs
@@ -0,0 +1,28 @@
+#[derive(PartialEq)]
+struct Foo {
+    x: isize,
+}
+
+fn foo() {
+    match () {
+        () if f == Foo { x: 42 } {}
+        //~^ ERROR expected one of `.`, `=>`, `?`, or an operator, found `{`
+        _ => {}
+    }
+}
+
+fn main() {
+    let x = 1;
+    let y = 2;
+    let value = 3;
+
+    match value {
+        Some(x) if x == y {
+            //~^ ERROR expected one of `!`, `.`, `::`, `=>`, `?`, or an operator, found `{`
+            x
+        },
+        _ => {
+            y
+        }
+    }
+}
diff --git a/src/test/ui/parser/missing-fat-arrow-after-match-guard.stderr b/src/test/ui/parser/missing-fat-arrow-after-match-guard.stderr
new file mode 100644
index 0000000000000..f2fd4ef844951
--- /dev/null
+++ b/src/test/ui/parser/missing-fat-arrow-after-match-guard.stderr
@@ -0,0 +1,24 @@
+error: expected one of `.`, `=>`, `?`, or an operator, found `{`
+  --> $DIR/missing-fat-arrow-after-match-guard.rs:8:34
+   |
+LL |         () if f == Foo { x: 42 } {}
+   |                                  ^ expected one of `.`, `=>`, `?`, or an operator
+   |
+help: try adding a fat arrow here
+   |
+LL |         () if f == Foo { x: 42 } => {}
+   |                                  ++
+
+error: expected one of `!`, `.`, `::`, `=>`, `?`, or an operator, found `{`
+  --> $DIR/missing-fat-arrow-after-match-guard.rs:20:27
+   |
+LL |         Some(x) if x == y {
+   |                           ^ expected one of `!`, `.`, `::`, `=>`, `?`, or an operator
+   |
+help: try adding a fat arrow here
+   |
+LL |         Some(x) if x == y => {
+   |                           ++
+
+error: aborting due to 2 previous errors
+