diff --git a/cli/src/commands/sync/sync.ts b/cli/src/commands/sync/sync.ts
index 32cff4a3cb..6185decc5a 100644
--- a/cli/src/commands/sync/sync.ts
+++ b/cli/src/commands/sync/sync.ts
@@ -1153,7 +1153,7 @@ export function ZipFSElement(
             ? "script"
             : p.endsWith(".resource.json")
               ? "resource"
-              : p.startsWith("dependencies/")
+              : isWorkspaceDependencies(p)
                 ? "dependencies"
                 : "other";
 
@@ -2752,7 +2752,7 @@ export async function compareDynFSElement(
       if (skipMetadata) {
         continue;
       }
-      if (k.startsWith("dependencies/")) {
+      if (isWorkspaceDependencies(k)) {
         if (!workspaceDependenciesPathToLanguageAndFilename(k)) {
           log.warn(`Skipping unrecognized workspace dependencies file: ${k}`);
           continue;
diff --git a/cli/src/types.ts b/cli/src/types.ts
index 5713d06390..866b2be21e 100644
--- a/cli/src/types.ts
+++ b/cli/src/types.ts
@@ -391,7 +391,7 @@ export function getTypeStrFromPath(
   if (isSharedLockPath(p)) {
     return "shared_lock";
   }
-  if (p.startsWith("dependencies" + SEP)) {
+  if (isWorkspaceDependencies(p)) {
     return "workspace_dependencies";
   }
   if (isFileResource(p) || isFilesetResource(p)) {
diff --git a/cli/src/utils/script_common.ts b/cli/src/utils/script_common.ts
index d804318491..611268c27c 100644
--- a/cli/src/utils/script_common.ts
+++ b/cli/src/utils/script_common.ts
@@ -45,7 +45,9 @@ export const workspaceDependenciesLanguages: WorkspaceDependenciesLanguage[] = [
 ] as const;
 
 export function workspaceDependenciesPathToLanguageAndFilename(path: string): { name: string | undefined, language: ScriptLanguage } | undefined {
-  const relativePath = path.replace("dependencies/", "");
+  // Sync paths carry the platform separator, while a set's name is always
+  // forward-slashed.
+  const relativePath = path.replaceAll("\\", "/").replace("dependencies/", "");
   for (const { filename, language } of workspaceDependenciesLanguages) {
     if (relativePath.endsWith(filename)) {
       return {
diff --git a/cli/src/utils/utils.ts b/cli/src/utils/utils.ts
index 0801c03911..526dffbde4 100644
--- a/cli/src/utils/utils.ts
+++ b/cli/src/utils/utils.ts
@@ -223,8 +223,9 @@ export function isRawAppFile(path: string): boolean {
   return isRawAppPath(path);
 }
 
+/** Sync paths carry the platform separator: `dependencies\x` on Windows. */
 export function isWorkspaceDependencies(path: string): boolean {
-  return path.startsWith("dependencies/");
+  return path.startsWith("dependencies/") || path.startsWith("dependencies\\");
 }
 
 export function printSync(input: string | Uint8Array) {
diff --git a/cli/test/gitsync_deploy_branch_config.test.ts b/cli/test/gitsync_deploy_branch_config.test.ts
index 39c435d872..eeab7a0120 100644
--- a/cli/test/gitsync_deploy_branch_config.test.ts
+++ b/cli/test/gitsync_deploy_branch_config.test.ts
@@ -63,7 +63,10 @@ test("git-sync fork deploy follows the fork branch's wmill.yaml", async () => {
       git(seed, "commit", "-m", "dedupe");
       git(seed, "push", "origin", forkBranch);
 
-      git(work, "clone", `file://${bare}`, ".");
+      // Git for Windows defaults to autocrlf=true, which checks the pulled LF
+      // files out as CRLF; the deploy's pull would rewrite every one of them
+      // and the clean-tree assertion below would read that as a change.
+      git(work, "clone", "-c", "core.autocrlf=false", `file://${bare}`, ".");
       const deployed = await backend.runCLICommand(
         [
           "sync",
diff --git a/cli/test/sync_pull_push.test.ts b/cli/test/sync_pull_push.test.ts
index 24c4a282a3..fa52510e6c 100644
--- a/cli/test/sync_pull_push.test.ts
+++ b/cli/test/sync_pull_push.test.ts
@@ -2185,18 +2185,20 @@ describe("settings sync", () => {
       const files = await listFilesRecursive(tempDir);
       expect(files).toContain("settings.yaml");
 
-      // Read and modify a safe setting (webhook URL)
+      // Read and modify a safe setting (webhook URL). The server resolves the
+      // webhook host when it is saved and refuses one that does not resolve to a
+      // public address, so this must be a real public hostname.
+      const webhook = "https://example.com/hook";
       const settingsContent = await readFile(`${tempDir}/settings.yaml`, "utf-8");
 
       let modifiedSettings: string;
       if (settingsContent.includes("webhook:")) {
         modifiedSettings = settingsContent.replace(
           /webhook:.*/,
-          'webhook: "https://test-webhook.example.com/hook"'
+          `webhook: "${webhook}"`
         );
       } else {
-        modifiedSettings =
-          settingsContent + '\nwebhook: "https://test-webhook.example.com/hook"\n';
+        modifiedSettings = settingsContent + `\nwebhook: "${webhook}"\n`;
       }
       await writeFile(`${tempDir}/settings.yaml`, modifiedSettings, "utf-8");
 
@@ -2213,7 +2215,7 @@ describe("settings sync", () => {
       );
       expect(apiResp.status).toEqual(200);
       const settingsData = await apiResp.json();
-      expect(settingsData.webhook).toEqual("https://test-webhook.example.com/hook");
+      expect(settingsData.webhook).toEqual(webhook);
     });
   });
 });
diff --git a/cli/test/workspace_deps_path_unit.test.ts b/cli/test/workspace_deps_path_unit.test.ts
new file mode 100644
index 0000000000..45d725c6e5
--- /dev/null
+++ b/cli/test/workspace_deps_path_unit.test.ts
@@ -0,0 +1,23 @@
+import { expect, test } from "bun:test";
+import { isWorkspaceDependencies } from "../src/utils/utils.ts";
+import { workspaceDependenciesPathToLanguageAndFilename } from "../src/utils/script_common.ts";
+
+// Sync paths carry the platform separator. A Windows path parsed to a different
+// set name pushes the file to a set the workspace does not have.
+test("workspace dependency paths parse the same with either separator", () => {
+  for (const sep of ["/", "\\"]) {
+    expect(isWorkspaceDependencies(`dependencies${sep}requirements.in`)).toBe(true);
+    expect(
+      workspaceDependenciesPathToLanguageAndFilename(`dependencies${sep}requirements.in`),
+    ).toEqual({ name: undefined, language: "python3" });
+    expect(
+      workspaceDependenciesPathToLanguageAndFilename(`dependencies${sep}team.package.json`),
+    ).toEqual({ name: "team", language: "bun" });
+    expect(
+      workspaceDependenciesPathToLanguageAndFilename(
+        `dependencies${sep}team${sep}python.requirements.in`,
+      ),
+    ).toEqual({ name: "team/python", language: "python3" });
+  }
+  expect(isWorkspaceDependencies("f\\dependencies\\requirements.in")).toBe(false);
+});