diff --git a/compiler/reporting/src/type_error.rs b/compiler/reporting/src/type_error.rs
index bd843e558b..0d21ae8fee 100644
--- a/compiler/reporting/src/type_error.rs
+++ b/compiler/reporting/src/type_error.rs
@@ -124,9 +124,9 @@ fn to_expr_report(
                     let problem = Concat(vec![
                         plain_text("This "),
                         code_text("if"),
-                        plain_text(" condition should be a "),
+                        plain_text(" condition needs to be a "),
                         ReportText::Type(Content::Alias(Symbol::BOOL_BOOL, vec![], Variable::BOOL)),
-                        plain_text(", but it isn’t."),
+                        plain_text("."),
                     ]);
 
                     report_bad_type(
@@ -137,10 +137,11 @@ fn to_expr_report(
                         region,
                         Some(expr_region),
                         problem,
-                        "Instead it’s",
+                        "Right now it’s",
                         Concat(vec![
+                            plain_text("I need every "),
                             code_text("if"),
-                            plain_text(" conditions must evaluate to a "),
+                            plain_text(" condition to evaluate to a "),
                             ReportText::Type(Content::Alias(
                                 Symbol::BOOL_BOOL,
                                 vec![],
diff --git a/compiler/reporting/tests/test_reporting.rs b/compiler/reporting/tests/test_reporting.rs
index 54a2a8b5a9..5bf5235946 100644
--- a/compiler/reporting/tests/test_reporting.rs
+++ b/compiler/reporting/tests/test_reporting.rs
@@ -766,16 +766,16 @@ mod test_reporting {
             ),
             indoc!(
                 r#"
-                This `if` condition should be a Bool, but it isn’t.
+                This `if` condition needs to be a Bool.
 
                 1 ┆  if "foo" then 2 else 3
                   ┆     ^^^^^
 
-                Instead it’s a string of type:
+                Right now it’s a string of type:
 
                     Str
 
-                `if` conditions must evaluate to a Bool—either `True` or `False`.
+                I need every `if` condition to evaluate to a Bool—either `True` or `False`.
 
                 "#
             ),