diff --git a/compiler/rustc_ast/src/tokenstream.rs b/compiler/rustc_ast/src/tokenstream.rs
index 4111182c3b7dc..74a8bc059ab18 100644
--- a/compiler/rustc_ast/src/tokenstream.rs
+++ b/compiler/rustc_ast/src/tokenstream.rs
@@ -978,10 +978,57 @@ pub struct DelimSpan {
 
 impl DelimSpan {
     pub fn from_single(sp: Span) -> Self {
-        DelimSpan { open: sp, close: sp }
+        let Some(sm) = rustc_span::source_map::get_source_map() else {
+            // No source map available.
+            return Self { open: sp, close: sp };
+        };
+
+        let (open, close) = sm
+            .span_to_source(sp, |src, start, end| {
+                let src = match src.get(start..end) {
+                    Some(s) if s.len() >= 2 => s.as_bytes(),
+                    _ => return Ok((sp, sp)),
+                };
+
+                // Only check the first and last characters.
+                // If there is white space or other characters
+                // other than `( ... )`, `[ ... ]`, and `{ ... }`.
+                // I assume that is intentionally included in this
+                // span so we don't want to shrink the span by
+                // searching for the delimiters, and setting
+                // the open and close spans to some more interior
+                // position.
+                let first = src[0];
+                let last = src[src.len() - 1];
+
+                // Thought maybe scan through if first is '(', '[',  or '{'
+                // and see if the last matches up (e.g. make sure it's not some
+                // extra mismatched delimiter)
+
+                let pos = (sp.hi() - sp.lo()).0.checked_sub(1).unwrap_or(0);
+                // If these return `None` just use the default because that
+                // means the span is too small for there to be a matched pair.
+                let Some(open) = sp.subspan(0..1) else {
+                    return Ok((sp, sp));
+                };
+                let Some(close) = sp.subspan(pos..) else {
+                    return Ok((sp, sp));
+                };
+
+                Ok(match (first, last) {
+                    (b'(', b')') | (b'{', b'}') | (b'[', b']') => (open, close),
+                    (_, _) => (sp, sp),
+                })
+            })
+            .ok()
+            .unwrap_or((sp, sp));
+
+        debug_assert!(open.lo() <= close.lo());
+        DelimSpan { open, close }
     }
 
     pub fn from_pair(open: Span, close: Span) -> Self {
+        debug_assert!(open.lo() <= close.lo());
         DelimSpan { open, close }
     }
 
@@ -990,6 +1037,7 @@ impl DelimSpan {
     }
 
     pub fn entire(self) -> Span {
+        debug_assert!(self.open.lo() <= self.close.lo());
         self.open.with_hi(self.close.hi())
     }
 }
diff --git a/compiler/rustc_span/src/lib.rs b/compiler/rustc_span/src/lib.rs
index 2e03ccb1aa1a3..72631f1050ee6 100644
--- a/compiler/rustc_span/src/lib.rs
+++ b/compiler/rustc_span/src/lib.rs
@@ -77,7 +77,7 @@ use std::cmp::{self, Ordering};
 use std::fmt::Display;
 use std::hash::Hash;
 use std::io::{self, Read};
-use std::ops::{Add, Range, Sub};
+use std::ops::{Add, Bound, Range, RangeBounds, Sub};
 use std::path::{Path, PathBuf};
 use std::str::FromStr;
 use std::sync::Arc;
@@ -1176,6 +1176,37 @@ impl Span {
     pub fn normalize_to_macro_rules(self) -> Span {
         self.map_ctxt(|ctxt| ctxt.normalize_to_macro_rules())
     }
+
+    /// This function is similar to `Span::from_inner`, but it
+    /// will return `None` if the relative Range span exceeds
+    /// the bounds of span.
+    pub fn subspan<I: Copy, R: RangeBounds<I>>(self, subspan: R) -> Option<Span>
+    where
+        u32: TryFrom<I>,
+    {
+        let lo = self.lo().0;
+        let hi = self.hi().0;
+
+        let start = match subspan.start_bound() {
+            Bound::Included(s) => u32::try_from(*s).ok()?,
+            Bound::Excluded(s) => u32::try_from(*s).ok()?.checked_add(1)?,
+            Bound::Unbounded => 0,
+        };
+
+        let end = match subspan.end_bound() {
+            Bound::Included(e) => u32::try_from(*e).ok()?.checked_add(1)?,
+            Bound::Excluded(e) => u32::try_from(*e).ok()?,
+            Bound::Unbounded => hi - lo,
+        };
+
+        let new_lo = lo.checked_add(start)?;
+        let new_hi = lo.checked_add(end)?;
+        if new_lo > hi || new_hi > hi {
+            return None;
+        }
+
+        Some(self.with_lo(BytePos(new_lo)).with_hi(BytePos(new_hi)))
+    }
 }
 
 impl Default for Span {