diff --git a/insta/src/snapshot.rs b/insta/src/snapshot.rs
index a1e1e2b7..9ff600b0 100644
--- a/insta/src/snapshot.rs
+++ b/insta/src/snapshot.rs
@@ -6,7 +6,11 @@ use std::io::{BufRead, BufReader, Write};
 use std::path::{Path, PathBuf};
 use std::time::{SystemTime, UNIX_EPOCH};
 
-use crate::content::{self, json, yaml, Content};
+use crate::{
+    content::{self, json, yaml, Content},
+    elog,
+    utils::style,
+};
 
 lazy_static::lazy_static! {
     static ref RUN_ID: String = {
@@ -268,7 +272,7 @@ impl MetaData {
     }
 }
 
-/// A helper to work with stored snapshots.
+/// A helper to work with file snapshots.
 #[derive(Debug, Clone)]
 pub struct Snapshot {
     module_name: String,
@@ -321,7 +325,7 @@ impl Snapshot {
                     }
                 }
             }
-            crate::elog!("A snapshot uses an old snapshot format; please update it to the new format with `cargo insta test --force-update-snapshots --accept`.\n\nSnapshot is at: {}", p.to_string_lossy());
+            elog!("A snapshot uses an old snapshot format; please update it to the new format with `cargo insta test --force-update-snapshots --accept`.\n\nSnapshot is at: {}", p.to_string_lossy());
             rv
         };
 
@@ -520,7 +524,8 @@ impl SnapshotContents {
         SnapshotContents(get_inline_snapshot_value(value))
     }
 
-    /// Returns the snapshot contents as string with surrounding whitespace removed.
+    /// Returns the snapshot contents as a normalized string (for example,
+    /// removing surrounding whitespace)
     pub fn as_str(&self) -> &str {
         let out = self.0.trim_start_matches(['\r', '\n']).trim_end();
         // Old inline snapshots have `---` at the start, so this strips that if
@@ -532,15 +537,36 @@ impl SnapshotContents {
         }
     }
 
-    /// Returns the snapshot contents as string without any trimming.
+    /// Returns the snapshot contents as string without any normalization
     pub fn as_str_exact(&self) -> &str {
         self.0.as_str()
     }
 
+    /// Matches another snapshot without any normalization
     pub fn matches_fully(&self, other: &SnapshotContents) -> bool {
         self.as_str_exact() == other.as_str_exact()
     }
 
+    /// Snapshot matches based on the latest format.
+    pub fn matches_latest(&self, other: &SnapshotContents) -> bool {
+        self.as_str() == other.as_str()
+    }
+
+    pub fn matches_legacy(&self, other: &SnapshotContents) -> bool {
+        fn as_str_legacy(sc: &SnapshotContents) -> &str {
+            let out = sc.as_str();
+            // Legacy inline snapshots have `---` at the start, so this strips that if
+            // it exists.
+            match out.strip_prefix("---\n") {
+                Some(old_snapshot) => old_snapshot,
+                None => out,
+            }
+        }
+        as_str_legacy(self) == as_str_legacy(other)
+    }
+
+    /// Create the literal string to write inline, adding `#` to escape the
+    /// value, indentation, delimiters
     pub fn to_inline(&self, indentation: usize) -> String {
         let contents = &self.0;
         let mut out = String::new();
@@ -570,8 +596,9 @@ impl SnapshotContents {
             out.extend(
                 contents
                     .lines()
-                    // newline needs to be at the start, since we don't want the end
-                    // finishing with a newline - the closing suffix should be on the same line
+                    // Adds an additional newline at the start of multiline
+                    // string (not sure this is the clearest way of representing
+                    // it, but it works...)
                     .map(|l| {
                         format!(
                             "\n{:width$}{l}",
@@ -580,7 +607,8 @@ impl SnapshotContents {
                             l = l
                         )
                     })
-                    // `lines` removes the final line ending - add back
+                    // `lines` removes the final line ending — add back. Include
+                    // indentation so the closing delimited aligns with the full string.
                     .chain(Some(format!("\n{:width$}", "", width = indentation))),
             );
         } else {
@@ -625,7 +653,15 @@ impl From<SnapshotContents> for String {
 
 impl PartialEq for SnapshotContents {
     fn eq(&self, other: &Self) -> bool {
-        self.as_str() == other.as_str()
+        // Ideally match on current rules, but otherwise fall back to legacy rules
+        if self.matches_latest(other) {
+            true
+        } else if self.matches_legacy(other) {
+            elog!("{} {}\n{}",style("Snapshot passes but is a legacy format. Please run `cargo insta test --force-update-snapshots --accept` to update to a newer format.").yellow().bold(),"Snapshot contents:", self.as_str());
+            true
+        } else {
+            false
+        }
     }
 }
 
@@ -719,7 +755,7 @@ fn get_inline_snapshot_value(frozen_value: &str) -> String {
     // (the only call site)
 
     if frozen_value.trim_start().starts_with('⋮') {
-        crate::elog!("A snapshot uses an old snapshot format; please update it to the new format with `cargo insta test --force-update-snapshots --accept`.\n\nSnapshot is at: {}", frozen_value);
+        elog!("A snapshot uses an old snapshot format; please update it to the new format with `cargo insta test --force-update-snapshots --accept`.\n\nSnapshot is at: {}", frozen_value);
 
         // legacy format - retain so old snapshots still work
         let mut buf = String::new();