diff --git a/lib/file-source/src/fingerprinter.rs b/lib/file-source/src/fingerprinter.rs
index 84bb2efe04d7d..69f5e690e22a1 100644
--- a/lib/file-source/src/fingerprinter.rs
+++ b/lib/file-source/src/fingerprinter.rs
@@ -77,6 +77,7 @@ enum SupportedCompressionAlgorithms {
 
 impl SupportedCompressionAlgorithms {
     fn values() -> Vec<SupportedCompressionAlgorithms> {
+        // Enumerate these from smallest magic_header_bytes to largest
         vec![SupportedCompressionAlgorithms::GZIP]
     }
 
@@ -88,39 +89,41 @@ impl SupportedCompressionAlgorithms {
 }
 
 trait UncompressedReader {
-    fn check(fp: &mut File) -> Option<SupportedCompressionAlgorithms>;
-    fn reader<'a>(fp: &'a mut File) -> Box<dyn BufRead + 'a>;
+    fn check(fp: &mut File) -> Result<Option<SupportedCompressionAlgorithms>, std::io::Error>;
+    fn reader<'a>(fp: &'a mut File) -> Result<Box<dyn BufRead + 'a>, std::io::Error>;
 }
 
 struct UncompressedReaderImpl;
 impl UncompressedReader for UncompressedReaderImpl {
-    fn check(fp: &mut File) -> Option<SupportedCompressionAlgorithms> {
-        SupportedCompressionAlgorithms::values()
-            .iter()
-            .find_map(|compression_algorithm| {
-                // magic headers for algorithms can be of different lengths, and using a buffer too long could exceed the length of the file
-                // so instantiate and check the various sizes independently
-                let magic_header_bytes = compression_algorithm.magic_header_bytes();
-                let mut magic = vec![0u8; magic_header_bytes.len()];
-
-                if fp.read_exact(&mut magic).is_ok()
-                    && fp.seek(SeekFrom::Start(0)).is_ok()
-                    && magic == magic_header_bytes
-                {
-                    Some(*compression_algorithm)
-                } else {
-                    None
-                }
-            })
+    fn check(fp: &mut File) -> Result<Option<SupportedCompressionAlgorithms>, std::io::Error> {
+        for compression_algorithm in SupportedCompressionAlgorithms::values() {
+            // magic headers for algorithms can be of different lengths, and using a buffer too long could exceed the length of the file
+            // so instantiate and check the various sizes in monotonically increasing order
+            let magic_header_bytes = compression_algorithm.magic_header_bytes();
+            let mut magic = vec![0u8; magic_header_bytes.len()];
+
+            let result = fp.read_exact(&mut magic);
+            let reset = fp.seek(SeekFrom::Start(0));
+            if reset.is_err() {
+                return Err(reset.unwrap_err());
+            } else if result.is_err() {
+                return Err(result.unwrap_err());
+            } else if magic == magic_header_bytes {
+                return Ok(Some(compression_algorithm));
+            } else {
+                continue;
+            }
+        }
+        return Ok(None);
     }
-    fn reader<'a>(fp: &'a mut File) -> Box<dyn BufRead + 'a> {
+    fn reader<'a>(fp: &'a mut File) -> Result<Box<dyn BufRead + 'a>, std::io::Error> {
         // To support new compression algorithms, add them below
-        match Self::check(fp) {
+        match Self::check(fp)? {
             Some(SupportedCompressionAlgorithms::GZIP) => {
-                Box::new(BufReader::new(GzDecoder::new(BufReader::new(fp))))
+                Ok(Box::new(BufReader::new(GzDecoder::new(BufReader::new(fp)))))
             }
             // No compression, or read the raw bytes
-            None => Box::new(BufReader::new(fp)),
+            None => Ok(Box::new(BufReader::new(fp))),
         }
     }
 }
@@ -164,7 +167,7 @@ impl Fingerprinter {
             } => {
                 buffer.resize(self.max_line_length, 0u8);
                 let mut fp = fs::File::open(path)?;
-                let mut reader = UncompressedReaderImpl::reader(&mut fp);
+                let mut reader = UncompressedReaderImpl::reader(&mut fp)?;
 
                 skip_first_n_bytes(&mut reader, ignored_header_bytes)?;
                 let bytes_read = fingerprinter_read_until(reader, b'\n', lines, buffer)?;
@@ -728,6 +731,22 @@ mod test {
             .is_none());
     }
 
+    #[test]
+    fn test_monotonic_compression_algorithms() {
+        // This test is necessary to handle an edge case where when assessing the magic header
+        // bytes of a file to determine the compression algorithm, it's possible that the length of
+        // the file is smaller than the size of the magic header bytes it's being assessed against.
+        // While this could be an indication that the file is simply too small, it could also
+        // just be that the compression header is a smaller one than the assessed algorithm.
+        // Checking this with a guarantee on the monotonically increasing order assures that this edge case doesn't happen.
+        let algos = super::SupportedCompressionAlgorithms::values();
+        let mut smallest_byte_length = 0;
+        for algo in algos {
+            let magic_header_bytes = algo.magic_header_bytes();
+            assert!(smallest_byte_length <= magic_header_bytes.len());
+            smallest_byte_length = magic_header_bytes.len();
+        }
+    }
     #[derive(Clone)]
     struct NoErrors;