diff --git a/crates/snapbox/src/data/format.rs b/crates/snapbox/src/data/format.rs
index 7ab71014..40464676 100644
--- a/crates/snapbox/src/data/format.rs
+++ b/crates/snapbox/src/data/format.rs
@@ -42,18 +42,66 @@ impl From<&std::path::Path> for DataFormat {
             .file_name()
             .and_then(|e| e.to_str())
             .unwrap_or_default();
-        let (file_stem, mut ext) = file_name.split_once('.').unwrap_or((file_name, ""));
-        if file_stem.is_empty() {
-            (_, ext) = file_stem.split_once('.').unwrap_or((file_name, ""));
+        let mut ext = file_name.strip_prefix('.').unwrap_or(file_name);
+        while let Some((_, new_ext)) = ext.split_once('.') {
+            ext = new_ext;
+            match ext {
+                #[cfg(feature = "json")]
+                "json" => {
+                    return DataFormat::Json;
+                }
+                #[cfg(feature = "json")]
+                "jsonl" => {
+                    return DataFormat::JsonLines;
+                }
+                #[cfg(feature = "term-svg")]
+                "term.svg" => {
+                    return Self::TermSvg;
+                }
+                _ => {}
+            }
         }
-        match ext {
-            #[cfg(feature = "json")]
-            "json" => DataFormat::Json,
-            #[cfg(feature = "json")]
-            "jsonl" => DataFormat::JsonLines,
-            #[cfg(feature = "term-svg")]
-            "term.svg" => Self::TermSvg,
-            _ => DataFormat::Text,
+        DataFormat::Text
+    }
+}
+
+#[cfg(test)]
+mod test {
+    use super::*;
+
+    #[test]
+    fn combos() {
+        #[cfg(feature = "json")]
+        let json = DataFormat::Json;
+        #[cfg(not(feature = "json"))]
+        let json = DataFormat::Text;
+        #[cfg(feature = "json")]
+        let jsonl = DataFormat::JsonLines;
+        #[cfg(not(feature = "json"))]
+        let jsonl = DataFormat::Text;
+        #[cfg(feature = "term-svg")]
+        let term_svg = DataFormat::TermSvg;
+        #[cfg(not(feature = "term-svg"))]
+        let term_svg = DataFormat::Text;
+        let cases = [
+            ("foo", DataFormat::Text),
+            (".foo", DataFormat::Text),
+            ("foo.txt", DataFormat::Text),
+            (".foo.txt", DataFormat::Text),
+            ("foo.stdout.txt", DataFormat::Text),
+            ("foo.json", json),
+            ("foo.stdout.json", json),
+            (".foo.json", json),
+            ("foo.jsonl", jsonl),
+            ("foo.stdout.jsonl", jsonl),
+            (".foo.jsonl", jsonl),
+            ("foo.term.svg", term_svg),
+            ("foo.stdout.term.svg", term_svg),
+            (".foo.term.svg", term_svg),
+        ];
+        for (input, output) in cases {
+            let input = std::path::Path::new(input);
+            assert_eq!(DataFormat::from(input), output, "for `{}`", input.display());
         }
     }
 }