feat(debug-files): extract embedded Portable PDBs from managed PEs

package.json

@@ -16,7 +16,7 @@
     "@sentry/core": "10.50.0",
     "@sentry/node-core": "10.50.0",
     "@sentry/sqlish": "^1.0.1",
-    "@sentry/symbolic": "13.5.0",
+    "@sentry/symbolic": "13.7.0",
     "@spotlightjs/spotlight": "^4.11.7",
     "@stricli/auto-complete": "^1.2.8",
     "@stricli/core": "1.2.7",

plugins/sentry-cli/skills/sentry-cli/references/dashboard.md

@@ -42,7 +42,7 @@ View a dashboard
 - `-w, --web - Open in browser`
 - `-f, --fresh - Bypass cache, re-detect projects, and fetch fresh data`
 - `-r, --refresh <value> - Auto-refresh interval in seconds (default: 60, min: 10)`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01"`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01"`
 
 **Examples:**
 

plugins/sentry-cli/skills/sentry-cli/references/event.md

@@ -37,7 +37,7 @@ List events for an issue
 - `-n, --limit <value> - Number of events (1-1000) - (default: "25")`
 - `-q, --query <value> - Search query (Sentry search syntax)`
 - `--full - Include full event body (stacktraces)`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01" - (default: "7d")`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01" - (default: "7d")`
 - `-f, --fresh - Bypass cache, re-detect projects, and fetch fresh data`
 - `-c, --cursor <value> - Navigate pages: "next", "prev", "first" (or raw cursor string)`
 

plugins/sentry-cli/skills/sentry-cli/references/explore.md

@@ -24,7 +24,7 @@ Query aggregate event data (Explore)
 - `-s, --sort <value> - Sort field (prefix with - for desc, e.g., "-count()")`
 - `-e, --environment <value>... - Replay environment filter for --dataset replays (repeatable, comma-separated)`
 - `-n, --limit <value> - Number of rows (1-1000) - (default: "25")`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01" - (default: "24h")`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01" - (default: "24h")`
 - `-f, --fresh - Bypass cache, re-detect projects, and fetch fresh data`
 - `-c, --cursor <value> - Navigate pages: "next", "prev", "first" (or raw cursor string)`
 

plugins/sentry-cli/skills/sentry-cli/references/issue.md

@@ -19,7 +19,7 @@ List issues in a project
 - `-q, --query <value> - Search query (Sentry syntax, implicit AND, no OR operator)`
 - `-n, --limit <value> - Maximum number of issues to list - (default: "25")`
 - `-s, --sort <value> - Sort by: recommended, date, new, freq, user (default: recommended on sentry.io, else date)`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01" - (default: "90d")`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01" - (default: "90d")`
 - `-c, --cursor <value> - Pagination cursor (use "next" for next page, "prev" for previous)`
 - `--compact - Single-line rows for compact output (auto-detects if omitted)`
 - `-f, --fresh - Bypass cache, re-detect projects, and fetch fresh data`
@@ -92,7 +92,7 @@ List events for a specific issue
 - `-n, --limit <value> - Number of events (1-1000) - (default: "25")`
 - `-q, --query <value> - Search query (Sentry search syntax)`
 - `--full - Include full event body (stacktraces)`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01" - (default: "7d")`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01" - (default: "7d")`
 - `-f, --fresh - Bypass cache, re-detect projects, and fetch fresh data`
 - `-c, --cursor <value> - Navigate pages: "next", "prev", "first" (or raw cursor string)`
 

plugins/sentry-cli/skills/sentry-cli/references/log.md

@@ -19,7 +19,7 @@ List logs from a project
 - `-n, --limit <value> - Number of log entries (1-1000) - (default: "100")`
 - `-q, --query <value> - Filter query (e.g., "level:error", "project:backend", "project:[a,b]")`
 - `-f, --follow <value> - Stream logs (optionally specify poll interval in seconds)`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01"`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01"`
 - `-s, --sort <value> - Sort order: "newest" (default) or "oldest" - (default: "newest")`
 - `--fresh - Bypass cache, re-detect projects, and fetch fresh data`
 

plugins/sentry-cli/skills/sentry-cli/references/replay.md

@@ -20,7 +20,7 @@ List recent Session Replays
 - `-q, --query <value> - Search query (Sentry replay search syntax)`
 - `-e, --environment <value>... - Filter by environment (repeatable, comma-separated)`
 - `-s, --sort <value> - Sort by: date, oldest, duration, errors, activity, or a raw replay sort field - (default: "date")`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01" - (default: "7d")`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01" - (default: "7d")`
 - `-f, --fresh - Bypass cache, re-detect projects, and fetch fresh data`
 - `-c, --cursor <value> - Navigate pages: "next", "prev", "first" (or raw cursor string)`
 

plugins/sentry-cli/skills/sentry-cli/references/span.md

@@ -19,7 +19,7 @@ List spans in a project or trace
 - `-n, --limit <value> - Number of spans (<=1000) - (default: "25")`
 - `-q, --query <value> - Filter spans (e.g., "op:db", "project:backend", "project:[cli,api]")`
 - `-s, --sort <value> - Sort order: date, duration - (default: "date")`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01" - (default: "7d")`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01" - (default: "7d")`
 - `-f, --fresh - Bypass cache, re-detect projects, and fetch fresh data`
 - `-c, --cursor <value> - Navigate pages: "next", "prev", "first" (or raw cursor string)`
 

plugins/sentry-cli/skills/sentry-cli/references/trace.md

@@ -19,7 +19,7 @@ List recent traces in a project
 - `-n, --limit <value> - Number of traces (1-1000) - (default: "25")`
 - `-q, --query <value> - Search query (Sentry search syntax)`
 - `-s, --sort <value> - Sort by: date, duration - (default: "date")`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01" - (default: "7d")`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01" - (default: "7d")`
 - `-f, --fresh - Bypass cache, re-detect projects, and fetch fresh data`
 - `-c, --cursor <value> - Navigate pages: "next", "prev", "first" (or raw cursor string)`
 
@@ -91,7 +91,7 @@ View logs associated with a trace
 
 **Flags:**
 - `-w, --web - Open trace in browser`
-- `-t, --period <value> - Time range: "7d", "2026-05-01..2026-06-01", ">=2026-05-01" - (default: "14d")`
+- `-t, --period <value> - Time range: "7d", "2026-06-01..2026-07-01", ">=2026-06-01" - (default: "14d")`
 - `-n, --limit <value> - Number of log entries (<=1000) - (default: "100")`
 - `-q, --query <value> - Filter query (e.g., "level:error", "project:backend", "project:[a,b]")`
 - `-s, --sort <value> - Sort order: "newest" (default) or "oldest" - (default: "newest")`

src/commands/debug-files/upload.ts

@@ -11,9 +11,10 @@
  * Honors the server-advertised `max_file_size` (oversized files are skipped)
  * and `max_wait` (clamps the processing wait). `.zip` archives are scanned in
  * place (disable with `--no-zips`); `--derived-data` additionally scans Xcode's
- * DerivedData folder on macOS. `--symbol-maps` (BCSymbolMap resolution) and
- * `--il2cpp-mapping` line mappings are deferred to follow-up PRs (see the
- * command's full description).
+ * DerivedData folder on macOS. Managed PE assemblies that embed a Portable PDB
+ * have it extracted and uploaded automatically as a separate DIF. `--symbol-maps`
+ * (BCSymbolMap resolution) and `--il2cpp-mapping` line mappings are deferred to
+ * follow-up PRs (see the command's full description).
  */
 
 import { createHash } from "node:crypto";
@@ -173,6 +174,9 @@ function difKey(dif: DebugFileUpload): string {
  * Convert prepared files into the DIF upload list, optionally appending a
  * source bundle per file when `--include-sources` is set.
  *
+ * Embedded Portable PDBs (extracted from managed PE assemblies during scanning)
+ * arrive here as ordinary prepared DIFs, so no special handling is needed.
+ *
  * Source files are read synchronously from the paths recorded in each object's
  * debug info; files not present locally are skipped. A bundle is only added
  * when it contains at least one source file.
@@ -454,6 +458,8 @@ export const uploadCommand = buildCommand({
       "  --no-zips        Do not scan inside .zip archives\n\n" +
       ".zip archives are scanned in place by default; nested archives are not " +
       "recursed.\n\n" +
+      "Managed PE assemblies (.NET) that embed a Portable PDB have it extracted " +
+      "and uploaded automatically as a separate <name>.pdb debug file.\n\n" +
       "Usage:\n" +
       "  sentry debug-files upload ./build\n" +
       "  sentry debug-files upload ./symbols.zip\n" +

src/lib/dif/index.ts

@@ -157,6 +157,60 @@ export function peekFormat(data: Uint8Array): string {
   return Archive.peek(data) ?? "unknown";
 }
 
+/** An embedded Portable PDB extracted from a managed PE object. */
+export type EmbeddedPpdbResult = {
+  /** The decompressed, standalone Portable PDB bytes. */
+  ppdb: Uint8Array;
+  /** Debug id of the PE the Portable PDB was embedded in (its advisory id). */
+  debugId: string;
+};
+
+/**
+ * Extract a Portable PDB embedded inside a managed Windows PE (.NET assembly).
+ *
+ * Managed PE images can carry their Portable PDB debug companion inline (debug
+ * directory entry type 17, deflate-compressed). This narrows each object in the
+ * archive to a PE via `ObjectFile.asPe()` and, for the first PE that embeds a
+ * Portable PDB, decompresses and returns those bytes together with that PE's
+ * debug id. The returned bytes are themselves a standalone Portable PDB that can
+ * be parsed and uploaded as a separate debug information file.
+ *
+ * Non-PE objects (and PEs without an embedded PPDB) are skipped, so this is safe
+ * to call unconditionally on any object file. A decompression/extraction error
+ * for an individual object is swallowed (logged at debug level) and treated as
+ * "no embedded PPDB", mirroring legacy `sentry-cli`, where a failed extraction
+ * never aborts the surrounding upload.
+ *
+ * @param data - The full contents of the object file (archive).
+ * @returns The embedded Portable PDB bytes plus the PE's debug id, or `null`
+ *   when no object in the archive embeds a Portable PDB.
+ * @throws If the buffer cannot be parsed as a known object format.
+ */
+export function extractEmbeddedPpdb(
+  data: Uint8Array
+): EmbeddedPpdbResult | null {
+  ensureInitialized();
+  const archive = new Archive(data);
+  for (const object of archive.objects()) {
+    const pe = object.asPe();
+    if (!pe) {
+      continue;
+    }
+    try {
+      const ppdb = pe.embeddedPpdb();
+      if (ppdb) {
+        return { ppdb, debugId: object.debugId };
+      }
+    } catch (err) {
+      log.debug(
+        `Failed to extract embedded Portable PDB for ${object.debugId}`,
+        err
+      );
+    }
+  }
+  return null;
+}
+
 /**
  * Select the single object that source-bundling operates on: the first object
  * that carries debug info, falling back to the first object in the archive.