diff --git a/extensions/ql-vscode/src/common/short-paths.ts b/extensions/ql-vscode/src/common/short-paths.ts
new file mode 100644
index 000000000..27eac829c
--- /dev/null
+++ b/extensions/ql-vscode/src/common/short-paths.ts
@@ -0,0 +1,111 @@
+import { platform } from "os";
+import { basename, dirname, join, normalize, resolve } from "path";
+import { lstat, readdir } from "fs/promises";
+import { extLogger } from "./logging/vscode";
+
+async function log(message: string): Promise<void> {
+  await extLogger.log(message);
+}
+
+/**
+ * Expand a single short path component
+ * @param dir The absolute path of the directory containing the short path component.
+ * @param shortBase The shot path component to expand.
+ * @returns The expanded path component.
+ */
+async function expandShortPathComponent(
+  dir: string,
+  shortBase: string,
+): Promise<string> {
+  await log(`Expanding short path component: ${shortBase}`);
+
+  const fullPath = join(dir, shortBase);
+
+  // Use `lstat` instead of `stat` to avoid following symlinks.
+  const stats = await lstat(fullPath, { bigint: true });
+  if (stats.dev === BigInt(0) || stats.ino === BigInt(0)) {
+    // No inode info, so we won't be able to find this in the directory listing.
+    await log(`No inode info available. Skipping.`);
+    return shortBase;
+  }
+  await log(`dev/inode: ${stats.dev}/${stats.ino}`);
+
+  try {
+    // Enumerate the children of the parent directory, and try to find one with the same dev/inode.
+    const children = await readdir(dir);
+    for (const child of children) {
+      await log(`considering child: ${child}`);
+      try {
+        const childStats = await lstat(join(dir, child), { bigint: true });
+        await log(`child dev/inode: ${childStats.dev}/${childStats.ino}`);
+        if (childStats.dev === stats.dev && childStats.ino === stats.ino) {
+          // Found a match.
+          await log(`Found a match: ${child}`);
+          return child;
+        }
+      } catch (e) {
+        // Can't read stats for the child, so skip it.
+        await log(`Error reading stats for child: ${e}`);
+      }
+    }
+  } catch (e) {
+    // Can't read the directory, so we won't be able to find this in the directory listing.
+    await log(`Error reading directory: ${e}`);
+    return shortBase;
+  }
+
+  await log(`No match found. Returning original.`);
+  return shortBase;
+}
+
+/**
+ * Expand the short path components in a path, including those in ancestor directories.
+ * @param shortPath The path to expand.
+ * @returns The expanded path.
+ */
+async function expandShortPathRecursive(shortPath: string): Promise<string> {
+  const shortBase = basename(shortPath);
+  if (shortBase.length === 0) {
+    // We've reached the root.
+    return shortPath;
+  }
+
+  const dir = await expandShortPathRecursive(dirname(shortPath));
+  await log(`dir: ${dir}`);
+  await log(`base: ${shortBase}`);
+  if (shortBase.indexOf("~") < 0) {
+    // This component doesn't have a short name, so just append it to the (long) parent.
+    await log(`Component is not a short name`);
+    return join(dir, shortBase);
+  }
+
+  // This component looks like it has a short name, so try to expand it.
+  const longBase = await expandShortPathComponent(dir, shortBase);
+  return join(dir, longBase);
+}
+
+/**
+ * Expands a path that potentially contains 8.3 short names (e.g. "C:\PROGRA~1" instead of "C:\Program Files").
+ * @param shortPath The path to expand.
+ * @returns A normalized, absolute path, with any short components expanded.
+ */
+export async function expandShortPaths(shortPath: string): Promise<string> {
+  const absoluteShortPath = normalize(resolve(shortPath));
+  if (platform() !== "win32") {
+    // POSIX doesn't have short paths.
+    return absoluteShortPath;
+  }
+
+  await log(`Expanding short paths in: ${absoluteShortPath}`);
+  // A quick check to see if there might be any short components.
+  // There might be a case where a short component doesn't contain a `~`, but if there is, I haven't
+  // found it.
+  // This may find long components that happen to have a '~', but that's OK.
+  if (absoluteShortPath.indexOf("~") < 0) {
+    // No short components to expand.
+    await log(`Skipping due to no short components`);
+    return absoluteShortPath;
+  }
+
+  return await expandShortPathRecursive(absoluteShortPath);
+}
diff --git a/extensions/ql-vscode/src/variant-analysis/run-remote-query.ts b/extensions/ql-vscode/src/variant-analysis/run-remote-query.ts
index 0b1f4f127..8938649a4 100644
--- a/extensions/ql-vscode/src/variant-analysis/run-remote-query.ts
+++ b/extensions/ql-vscode/src/variant-analysis/run-remote-query.ts
@@ -38,6 +38,7 @@ import type { QueryLanguage } from "../common/query-language";
 import { tryGetQueryMetadata } from "../codeql-cli/query-metadata";
 import { askForLanguage, findLanguage } from "../codeql-cli/query-language";
 import type { QlPackFile } from "../packaging/qlpack-file";
+import { expandShortPaths } from "../common/short-paths";
 
 /**
  * Well-known names for the query pack used by the server.
@@ -286,10 +287,16 @@ interface RemoteQueryTempDir {
 }
 
 async function createRemoteQueriesTempDirectory(): Promise<RemoteQueryTempDir> {
-  const remoteQueryDir = await dir({
+  const shortRemoteQueryDir = await dir({
     dir: tmpDir.name,
     unsafeCleanup: true,
   });
+  // Expand 8.3 filenames here to work around a CLI bug where `codeql pack bundle` produces an empty
+  // archive if the pack path contains any 8.3 components.
+  const remoteQueryDir = {
+    ...shortRemoteQueryDir,
+    dir: expandShortPaths(shortRemoteQueryDir.path),
+  };
   const queryPackDir = join(remoteQueryDir.path, "query-pack");
   await mkdirp(queryPackDir);
   const compiledPackDir = join(remoteQueryDir.path, "compiled-pack");