diff --git a/docs/snapshots/2026-01-29-debug-files-upload-compression.md b/docs/snapshots/2026-01-29-debug-files-upload-compression.md
new file mode 100644
index 0000000000..f168088f50
--- /dev/null
+++ b/docs/snapshots/2026-01-29-debug-files-upload-compression.md
@@ -0,0 +1,106 @@
+# Debug files upload compression findings
+
+## Conversation summary
+- `debug-files upload` does not compress whole debug files; it uploads raw bytes
+  in chunks and only applies per-chunk transport compression (gzip or
+  uncompressed).
+- There is no CLI option to compress entire debug files before upload.
+- The symbolic crates (v12.16.3) do not expose a whole-file DIF compression API.
+  They only decompress compressed sections or embedded payloads when reading,
+  and provide ZIP creation for source bundles.
+- `symsorter` in the symbolicator repo performs whole-file compression itself
+  using zstd, with `-z/-zz/-zzz` mapping to zstd levels. Symbolic is used there
+  only for parsing/iterating objects.
+- A symsorter-compressed file passed to `sentry-cli debug-files upload` would be
+  skipped because format detection relies on object-file magic bytes; zstd
+  wrappers do not match any supported DIF format. There is no whole-file
+  decompression step in the upload path. If the format check were bypassed, the
+  raw compressed bytes would be uploaded (still subject to per-chunk transport
+  compression).
+- Extracting the symsorter compression logic into symbolic would likely require
+  a small public helper in `symbolic-debuginfo` (or similar) that wraps zstd
+  encoding, and then updating symsorter to call it while keeping the CLI's
+  compression-level mapping in symsorter.
+
+## Question
+Does `debug-files upload` ever compress the entire debug file before uploading
+(not just transport-level chunk compression)?
+
+## Findings
+- The `debug-files upload` command delegates to `DifUpload::upload` and does
+  not apply any whole-file compression step to DIFs before upload.
+  It scans files, builds `DifMatch` objects, and uploads them via the
+  chunked upload path without wrapping the full DIF in a compressed container.
+  (See `src/commands/debug_files/upload.rs:L225-L294`,
+  `src/utils/dif_upload/mod.rs:L1166-L1204`.)
+- Each DIF is chunked directly from its raw bytes. `DifMatch` implements
+  `AsRef<[u8]>` by returning `data()`; `Chunked::from` computes checksums and
+  splits those bytes into chunks. There is no full-file compression step here.
+  (See `src/utils/dif_upload/mod.rs:L259-L262`,
+  `src/utils/chunks/types.rs:L60-L73`.)
+- Compression only happens per chunk when uploading: `Api::upload_chunks`
+  compresses each chunk with `Api::compress` (gzip or uncompressed) and sends it
+  as multipart data. This is transport-level compression, not a single
+  compressed DIF.
+  (See `src/api/mod.rs:L354-L392`.)
+
+## Notes
+- When `--include-sources` is used, sentry-cli generates source bundle archives
+  via `SourceBundleWriter` and uploads those bundles as separate DIFs. This is
+  creation of a new archive artifact, not compression of the original DIF
+  itself. (See `src/utils/dif_upload/mod.rs:L1052-L1098`.)
+
+## Symbolic crate findings (v12.16.3)
+- The symbolic crate documentation focuses on symbolication and debug info
+  parsing (object formats, symcache, minidump, etc.) and does not describe an
+  API for compressing entire debug files. (See
+  `/workspace/.cargo/registry/src/index.crates.io-1949cf8c6b5b557f/symbolic-12.16.3/README.md`
+  and `src/lib.rs`.)
+- `symbolic-debuginfo` includes **decompression** support for compressed data
+  inside debug files (e.g., compressed DWARF sections and embedded portable PDB
+  payloads), but this is for reading/expanding data on access, not for creating
+  compressed DIFs. (See
+  `symbolic-debuginfo-12.16.3/src/dwarf.rs:L182-L205`,
+  `symbolic-debuginfo-12.16.3/src/elf.rs:L577-L626`,
+  `symbolic-debuginfo-12.16.3/src/pe.rs:L502-L523`.)
+- The only write-side “compression” in symbolic is for **source bundles**: the
+  `SourceBundleWriter` builds a ZIP archive using `ZipWriter`, which is a
+  separate artifact type and not a general-purpose DIF compressor. (See
+  `symbolic-debuginfo-12.16.3/src/sourcebundle/mod.rs:L1076-L1139` and
+  `L1114-L1121`.)
+
+## Symsorter implementation (symbolicator repo)
+- `symsorter` implements whole-file compression itself, using the `zstd` crate
+  directly. The `--compress/-z` flag increments a `compression_level`, which is
+  mapped to zstd levels and applied when writing each object to disk with
+  `zstd::stream::copy_encode`. (See
+  `symbolicator/crates/symsorter/src/app.rs`, `Cli::compression_level` and
+  `process_file` where `copy_encode(obj.data(), &mut out, compression_level)` is
+  called.)
+- `symbolic` is used for parsing and iterating over objects (`Archive`, `Object`,
+  `ObjectKind`), but compression is performed in symsorter, not via symbolic
+  APIs. (See `symbolicator/crates/symsorter/src/app.rs` imports and usage.)
+
+## CLI compression option
+- `debug-files upload` does not expose a flag to compress whole debug files
+  before upload. The upload path only applies per-chunk transport compression
+  negotiated with the server. (See `src/commands/debug_files/upload.rs` and
+  `src/api/mod.rs:L354-L392`.)
+
+## Symsorter-compressed file uploaded via sentry-cli
+- DIF discovery uses `Archive::peek` to identify object formats. If the format
+  is `Unknown`, the file is skipped during collection. (See
+  `src/utils/dif_upload/mod.rs:L733-L754`.)
+- `Archive::peek` looks for known object magic bytes (ELF, PE, Mach-O, PDB,
+  etc.) and does not recognize zstd wrappers. (See
+  `symbolic-debuginfo-12.16.3/src/object.rs:L127-L172`.)
+- There is no whole-file decompression step in the upload path, so a symsorter
+  zstd-wrapped file would not be decompressed by sentry-cli. If the format check
+  were bypassed, the raw compressed bytes would be uploaded.
+
+## Extracting symsorter compression into symbolic (discussion)
+- This would require adding a public helper (likely in `symbolic-debuginfo`) to
+  zstd-compress raw bytes or write a compressed stream, then updating symsorter
+  to call that helper.
+- The policy mapping of `-z/-zz/-zzz` to zstd levels is CLI-specific and should
+  remain in symsorter, while symbolic would accept a raw zstd level.