diff --git a/apps/web/hooks/use-document-mutations.test.ts b/apps/web/hooks/use-document-mutations.test.ts
new file mode 100644
index 00000000..1ec4f211
--- /dev/null
+++ b/apps/web/hooks/use-document-mutations.test.ts
@@ -0,0 +1,177 @@
+import { afterAll, beforeEach, describe, expect, it, mock } from "bun:test"
+
+type SpaceSettingsResult =
+	| { containerTag: string; entityContext: string | null; name: string | null }
+	| Error
+
+type DocumentRequest = {
+	body?: Record<string, unknown>
+}
+
+let spaceSettingsResult: SpaceSettingsResult = new Error(
+	"space settings result not configured",
+)
+const documentRequests: { route: string; options: DocumentRequest }[] = []
+const fileRequestBodies: (FormData | null)[] = []
+
+const fetchQuery = mock(async () => {
+	if (spaceSettingsResult instanceof Error) throw spaceSettingsResult
+	return spaceSettingsResult
+})
+
+const originalFetch = globalThis.fetch
+const uploadFetch = mock(
+	async (
+		_input: Parameters<typeof fetch>[0],
+		init?: Parameters<typeof fetch>[1],
+	): Promise<Response> => {
+		fileRequestBodies.push(init?.body instanceof FormData ? init.body : null)
+		return Response.json({ id: "document-1" })
+	},
+)
+globalThis.fetch = Object.assign(uploadFetch, {
+	preconnect: originalFetch.preconnect,
+})
+
+mock.module("@tanstack/react-query", () => ({
+	useMutation: (options: {
+		mutationFn: (variables: unknown) => Promise<unknown>
+	}) => ({ mutateAsync: options.mutationFn }),
+	useQuery: () => ({}),
+	useQueryClient: () => ({ fetchQuery }),
+}))
+
+mock.module("sonner", () => ({
+	toast: {
+		error: () => {},
+		success: () => {},
+		warning: () => {},
+	},
+}))
+
+mock.module("@lib/api", () => ({
+	$fetch: async (route: string, options: DocumentRequest = {}) => {
+		documentRequests.push({ route, options })
+		return { data: { id: "document-1" }, error: null }
+	},
+}))
+
+mock.module("@lib/auth-context", () => ({
+	useAuth: () => ({ user: { name: "Ada" } }),
+}))
+
+mock.module("@/lib/analytics", () => ({
+	analytics: {
+		documentAdded: () => {},
+		documentDeleted: () => {},
+		documentEdited: () => {},
+		documentsBulkDeleted: () => {},
+	},
+}))
+
+const { useDocumentMutations } = await import("./use-document-mutations")
+
+afterAll(() => {
+	globalThis.fetch = originalFetch
+	mock.restore()
+})
+
+const defaultEntityContext =
+	"This is Ada, saving items in a personal knowledge management system. This may be websites, links, notes, journals, PDFs, etc. Understand the user from it into a graph."
+
+async function saveNote() {
+	const { noteMutation } = useDocumentMutations()
+	await noteMutation.mutateAsync({ content: "A note", project: "space-1" })
+	return documentRequests[0]
+}
+
+async function uploadFile() {
+	const { fileMutation } = useDocumentMutations()
+	await fileMutation.mutateAsync({
+		fileEntries: [
+			{
+				id: "file-1",
+				file: new File(["contents"], "note.txt", { type: "text/plain" }),
+			},
+		],
+		project: "space-1",
+	})
+	return fileRequestBodies[0]
+}
+
+describe("document mutation entity context", () => {
+	beforeEach(() => {
+		spaceSettingsResult = new Error("space settings result not configured")
+		documentRequests.length = 0
+		fileRequestBodies.length = 0
+		fetchQuery.mockClear()
+		uploadFetch.mockClear()
+	})
+
+	it("omits the default when the space has a configured context", async () => {
+		spaceSettingsResult = {
+			containerTag: "space-1",
+			entityContext: "Remember work decisions",
+			name: "Work",
+		}
+
+		const request = await saveNote()
+
+		expect(request).toEqual({
+			route: "@post/documents",
+			options: {
+				body: {
+					content: "A note",
+					containerTags: ["space-1"],
+					metadata: { sm_source: "consumer" },
+				},
+			},
+		})
+		expect(fetchQuery).toHaveBeenCalledTimes(1)
+	})
+
+	it("includes the default after settings confirm the context is empty", async () => {
+		spaceSettingsResult = {
+			containerTag: "space-1",
+			entityContext: null,
+			name: "Personal",
+		}
+
+		const request = await saveNote()
+
+		expect(request?.options.body).toEqual({
+			content: "A note",
+			containerTags: ["space-1"],
+			entityContext: defaultEntityContext,
+			metadata: { sm_source: "consumer" },
+		})
+	})
+
+	it("still saves but omits the context when settings cannot be read", async () => {
+		spaceSettingsResult = new Error("settings unavailable")
+
+		const request = await saveNote()
+
+		expect(request).toEqual({
+			route: "@post/documents",
+			options: {
+				body: {
+					content: "A note",
+					containerTags: ["space-1"],
+					metadata: { sm_source: "consumer" },
+				},
+			},
+		})
+		expect(fetchQuery).toHaveBeenCalledTimes(1)
+	})
+
+	it("omits the context from file uploads when settings cannot be read", async () => {
+		spaceSettingsResult = new Error("settings unavailable")
+
+		const formData = await uploadFile()
+
+		expect(formData?.get("containerTags")).toBe('["space-1"]')
+		expect(formData?.get("entityContext")).toBeNull()
+		expect(uploadFetch).toHaveBeenCalledTimes(1)
+	})
+})
diff --git a/apps/web/hooks/use-document-mutations.ts b/apps/web/hooks/use-document-mutations.ts
index 7f0e6384..a467e103 100644
--- a/apps/web/hooks/use-document-mutations.ts
+++ b/apps/web/hooks/use-document-mutations.ts
@@ -230,7 +230,7 @@ export function useDocumentMutations({
 
 	const defaultEntityContext = `This is ${user?.name ?? "a user"}, saving items in a personal knowledge management system. This may be websites, links, notes, journals, PDFs, etc. Understand the user from it into a graph.`
 
-	// Skip when the space has its own context — sending one would overwrite the stored value.
+	// Only send the default after settings confirm the context is empty; otherwise it could overwrite the stored value.
 	const resolveEntityContext = async (
 		project: string,
 	): Promise<string | undefined> => {
@@ -242,7 +242,7 @@ export function useDocumentMutations({
 			})
 			return settings?.entityContext ? undefined : defaultEntityContext
 		} catch {
-			return defaultEntityContext
+			return undefined
 		}
 	}