diff --git a/crates/compiler/fmt/src/expr.rs b/crates/compiler/fmt/src/expr.rs
index b0aa8101f2..4d1bea1acd 100644
--- a/crates/compiler/fmt/src/expr.rs
+++ b/crates/compiler/fmt/src/expr.rs
@@ -788,6 +788,7 @@ fn fmt_parens(sub_expr: &Expr<'_>, buf: &mut Buf<'_>, indent: u16) {
     let should_add_newlines = match sub_expr {
         Expr::Closure(..)
         | Expr::SpaceBefore(..)
+        | Expr::When(..)
         | Expr::SpaceAfter(Expr::Closure(..), ..)
         | Expr::DbgStmt { .. } => false,
         _ => sub_expr.is_multiline(),
@@ -881,7 +882,7 @@ fn starts_with_newline(expr: &Expr) -> bool {
         SpaceBefore(_, comment_or_newline) => {
             matches!(comment_or_newline.first(), Some(CommentOrNewline::Newline))
         }
-        DbgStmt { .. } => true,
+        DbgStmt { .. } | When(..) => true,
         _ => false,
     }
 }
@@ -1724,7 +1725,20 @@ fn fmt_when<'a>(
             buf.indent(indent + INDENT);
             buf.push_str(" if");
             buf.spaces(1);
-            guard_expr.format_with_options(buf, Parens::NotNeeded, Newlines::Yes, indent + INDENT);
+
+            let guard_lifted =
+                expr_lift_spaces(Parens::NotNeeded, buf.text.bump(), &guard_expr.value);
+
+            if guard_needs_parens(&guard_lifted.item) {
+                fmt_parens(&lower(buf.text.bump(), guard_lifted), buf, indent + INDENT);
+            } else {
+                lower(buf.text.bump(), guard_lifted).format_with_options(
+                    buf,
+                    Parens::NotNeeded,
+                    Newlines::Yes,
+                    indent + INDENT,
+                );
+            }
         }
 
         buf.indent(indent + INDENT);
@@ -1741,7 +1755,6 @@ fn fmt_when<'a>(
             buf.spaces(1);
         }
 
-        // expr.format_with_options(buf, Parens::NotNeeded, Newlines::Yes, inner_indent);
         format_expr_only(
             &expr.item,
             buf,
@@ -1760,6 +1773,16 @@ fn fmt_when<'a>(
     }
 }
 
+fn guard_needs_parens(value: &Expr<'_>) -> bool {
+    match value {
+        Expr::When(..) => true,
+        Expr::ParensAround(expr) | Expr::SpaceBefore(expr, _) | Expr::SpaceAfter(expr, _) => {
+            guard_needs_parens(expr)
+        }
+        _ => false,
+    }
+}
+
 fn fmt_dbg_stmt<'a>(
     buf: &mut Buf,
     condition: &'a Loc<Expr<'a>>,
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/when_in_binops.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/when_in_binops.expr.formatted.roc
index 1605846682..15c66c8655 100644
--- a/crates/compiler/test_syntax/tests/snapshots/pass/when_in_binops.expr.formatted.roc
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/when_in_binops.expr.formatted.roc
@@ -4,6 +4,5 @@ di
     when
         b
     is
-        7 -> 7e
-)
+        7 -> 7e)
     zl
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/when_in_when_guard_wtf.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/when_in_when_guard_wtf.expr.formatted.roc
new file mode 100644
index 0000000000..c9b3d03a03
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/when_in_when_guard_wtf.expr.formatted.roc
@@ -0,0 +1,10 @@
+when
+    f
+is
+    s if (
+        when
+            0
+        is
+            z ->
+                f
+                    z) -> m
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/when_in_when_guard_wtf.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/when_in_when_guard_wtf.expr.result-ast
new file mode 100644
index 0000000000..0e6d6b4d85
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/when_in_when_guard_wtf.expr.result-ast
@@ -0,0 +1,74 @@
+@0-35 SpaceAfter(
+    When(
+        @5-6 SpaceAfter(
+            Var {
+                module_name: "",
+                ident: "f",
+            },
+            [
+                Newline,
+            ],
+        ),
+        [
+            WhenBranch {
+                patterns: [
+                    @10-11 SpaceBefore(
+                        Identifier {
+                            ident: "s",
+                        },
+                        [
+                            Newline,
+                        ],
+                    ),
+                ],
+                value: @34-35 Var {
+                    module_name: "",
+                    ident: "m",
+                },
+                guard: Some(
+                    @15-32 When(
+                        @20-21 SpaceAfter(
+                            Num(
+                                "0",
+                            ),
+                            [
+                                Newline,
+                            ],
+                        ),
+                        [
+                            WhenBranch {
+                                patterns: [
+                                    @25-26 Identifier {
+                                        ident: "z",
+                                    },
+                                ],
+                                value: @28-32 Apply(
+                                    @28-29 Var {
+                                        module_name: "",
+                                        ident: "f",
+                                    },
+                                    [
+                                        @31-32 SpaceBefore(
+                                            Var {
+                                                module_name: "",
+                                                ident: "z",
+                                            },
+                                            [
+                                                Newline,
+                                            ],
+                                        ),
+                                    ],
+                                    Space,
+                                ),
+                                guard: None,
+                            },
+                        ],
+                    ),
+                ),
+            },
+        ],
+    ),
+    [
+        Newline,
+    ],
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/when_in_when_guard_wtf.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/when_in_when_guard_wtf.expr.roc
new file mode 100644
index 0000000000..654521187c
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/when_in_when_guard_wtf.expr.roc
@@ -0,0 +1,5 @@
+when f
+is
+s if when 0
+is z->f
+ z->m
diff --git a/crates/compiler/test_syntax/tests/test_snapshots.rs b/crates/compiler/test_syntax/tests/test_snapshots.rs
index 21fd0d761e..523c97435f 100644
--- a/crates/compiler/test_syntax/tests/test_snapshots.rs
+++ b/crates/compiler/test_syntax/tests/test_snapshots.rs
@@ -764,6 +764,7 @@ mod test_snapshots {
         pass/when_in_list.expr,
         pass/when_in_parens.expr,
         pass/when_in_parens_indented.expr,
+        pass/when_in_when_guard_wtf.expr,
         pass/when_newline_after_condition.expr,
         pass/when_newline_before_is_and_in_branch_parens.expr,
         pass/when_result_list.expr,