A text file can arrive successfully but differ from the original because the transfer deliberately changed its line-ending format. That is a different question from a connection dropping or a file being truncated. Establish whether the recipient needs identical bytes or a particular text convention before choosing a transfer mode.

This workflow concerns an ordinary WinSCP file transfer using a protocol that offers Text and Binary modes. Keep the source unchanged and choose a new test destination. Do not overwrite the only known-good copy while investigating why two files differ.

Decide whether conversion belongs in this transfer

Text mode can convert a text file into the destination platform's format. It is unsuitable for binary files, including modern Word documents, which must be transferred without such changes. Binary mode is the appropriate starting point when the file content must arrive unchanged.

WinSCP's Automatic mode selects the mode from the filename using a configurable text-file mask, usually based on extensions. It does not establish the intended meaning of an unfamiliar export. Inspect the active transfer settings and explicitly choose Binary for this comparison.

For example, an export named records.txt may be required to match a supplied digest exactly. Its text-like name does not authorise newline conversion. Conversely, a receiving system may explicitly require a different line-ending convention; document that transformation as a separate requirement rather than calling the resulting difference unexplained damage.

Compare the completed copy with the correct expectation

Transfer the retained source to the new destination and wait for completion. Use an appropriate checksum comparison for the stable source and destination, then open the result in its intended application. Content identity and application acceptance are separate observations.

If the digest still differs, confirm the file pair and whether either copy changed after transfer. Keep the observed mode and filenames with the report instead of repeatedly switching settings without preserving a comparison.

Be aware that WinSCP's remote-editing workflow can force Text mode separately from ordinary transfer settings. If the discrepancy follows opening and saving in an editor, investigate that path specifically; the successful Binary transfer does not prove what a later edit did.

Keep the accepted transfer rule with the handover. A deliberate byte-preserving copy should be identifiable from its settings and verification, not merely from the absence of a progress error.

Sources: WinSCP documentation.