diff --git a/crates/common/src/format.rs b/crates/common/src/format.rs
index 4357a0c66..28afac735 100644
--- a/crates/common/src/format.rs
+++ b/crates/common/src/format.rs
@@ -1618,6 +1618,12 @@ impl FormatString {
             let right = &text[pos..];
             let format_part = Self::parse_part_in_brackets(&left)?;
             Ok((format_part, &right[1..]))
+        } else if text.len() == 1 {
+            // Nothing follows the brace, so it is a stray one rather than a field
+            // that was left open: CPython separates "{" and "a{" from "{0" and
+            // "a{b" the same way. `{` is one byte, so a length of one is the brace
+            // on its own.
+            Err(FormatParseError::UnescapedStartBracketInLiteral)
         } else {
             Err(FormatParseError::UnmatchedBracket)
         }
@@ -2338,6 +2344,26 @@ mod tests {
         );
     }
 
+    #[test]
+    fn format_parse_lone_start_bracket() {
+        // A brace with nothing after it is a stray brace; one holding a field
+        // that was never closed is not. CPython words the two differently.
+        for lone in ["{", "a{"] {
+            assert_eq!(
+                FormatString::from_str(lone.as_ref()),
+                Err(FormatParseError::UnescapedStartBracketInLiteral),
+                "{lone:?}"
+            );
+        }
+        for unclosed in ["{s", "a{b", "{0"] {
+            assert_eq!(
+                FormatString::from_str(unclosed.as_ref()),
+                Err(FormatParseError::UnmatchedBracket),
+                "{unclosed:?}"
+            );
+        }
+    }
+
     #[test]
     fn square_brackets_inside_format() {
         assert_eq!(
diff --git a/crates/vm/src/format.rs b/crates/vm/src/format.rs
index 9a54df3b4..d95def768 100644
--- a/crates/vm/src/format.rs
+++ b/crates/vm/src/format.rs
@@ -103,12 +103,36 @@ impl IntoPyException for FormatSpecError {
 
 impl ToPyException for FormatParseError {
     fn to_pyexception(&self, vm: &VirtualMachine) -> PyBaseExceptionRef {
+        // Matched exhaustively on purpose: a catch-all sent most of these to
+        // "Unexpected error parsing format string", which tells the reader nothing
+        // about the format string they mistyped.
         match self {
-            Self::UnmatchedBracket => vm.new_value_error("expected '}' before end of string"),
+            Self::UnmatchedBracket | Self::MissingRightBracket => {
+                vm.new_value_error("expected '}' before end of string")
+            }
+            Self::MissingStartBracket => {
+                vm.new_value_error("Single '}' encountered in format string")
+            }
+            // A brace in literal text that was not doubled, i.e. a stray `{` with
+            // nothing after it. `parse_spec` reports this rather than
+            // UnmatchedBracket so that "{" and "a{" are separated from "{0" and
+            // "a{b", which are fields left open.
+            Self::UnescapedStartBracketInLiteral => {
+                vm.new_value_error("Single '{' encountered in format string")
+            }
+            Self::InvalidFormatSpecifier => vm.new_value_error("unmatched '{' in format spec"),
+            // Reached both for a conversion that is not one character (`{0!xy}`,
+            // where CPython says "expected ':' after conversion specifier") and for
+            // an empty one (`{0!}`, "unmatched '{' in format spec"). Telling those
+            // apart needs the parser to say which, so the generic message stays.
+            Self::UnknownConversion => vm.new_value_error("Unexpected error parsing format string"),
+            Self::EmptyAttribute => vm.new_value_error("Empty attribute in format string"),
+            Self::InvalidCharacterAfterRightBracket => {
+                vm.new_value_error("Only '.' or '[' may follow ']' in format field specifier")
+            }
             Self::TooManyDecimalDigits => {
                 vm.new_value_error("Too many decimal digits in format string")
             }
-            _ => vm.new_value_error("Unexpected error parsing format string"),
         }
     }
 }
diff --git a/extra_tests/snippets/builtin_format.py b/extra_tests/snippets/builtin_format.py
index 844d9e451..920256c0d 100644
--- a/extra_tests/snippets/builtin_format.py
+++ b/extra_tests/snippets/builtin_format.py
@@ -336,3 +336,45 @@ assert_raises(ValueError, format, True, ".2")
 assert_raises(ValueError, format, True, "5.2")
 assert_raises(ValueError, format, True, "z")
 assert_raises(ValueError, format, True, "s")
+
+
+def test_format_parse_error_messages():
+    # Most FormatParseError variants used to fall into a catch-all that said
+    # "Unexpected error parsing format string", which does not say what is wrong
+    # with the format string. Messages are CPython 3.14.0's.
+    def message(fmt, *args):
+        try:
+            fmt.format(*args)
+        except ValueError as err:
+            return str(err)
+        raise AssertionError("ValueError was not raised for " + repr(fmt))
+
+    assert message("a}b") == "Single '}' encountered in format string"
+    assert message("{{a}") == "Single '}' encountered in format string"
+
+    assert message("{0.}", 1) == "Empty attribute in format string"
+    assert message("{0[]}", [1]) == "Empty attribute in format string"
+
+    assert message("{0[1}", [1, 2]) == "expected '}' before end of string"
+    assert message("{0", 1) == "expected '}' before end of string"
+
+    assert (
+        message("{0[0]x}", [1])
+        == "Only '.' or '[' may follow ']' in format field specifier"
+    )
+    assert (
+        message("{0[0]]}", [1])
+        == "Only '.' or '[' may follow ']' in format field specifier"
+    )
+
+    assert message("{:{{}}", 1) == "unmatched '{' in format spec"
+
+    # A brace with nothing after it is a stray brace; one holding an unclosed
+    # field is not.
+    assert message("{") == "Single '{' encountered in format string"
+    assert message("a{") == "Single '{' encountered in format string"
+    assert message("{s") == "expected '}' before end of string"
+    assert message("a{b") == "expected '}' before end of string"
+
+
+test_format_parse_error_messages()