diff --git a/.changeset/deploy-positional-path-telemetry.md b/.changeset/deploy-positional-path-telemetry.md
new file mode 100644
index 0000000000..9c265d9c5e
--- /dev/null
+++ b/.changeset/deploy-positional-path-telemetry.md
@@ -0,0 +1,7 @@
+---
+"wrangler": minor
+---
+
+Categorise the positional path argument to `wrangler deploy` and `wrangler versions upload` in command telemetry
+
+Command telemetry now records a coarse category for the entry-point/assets positional (`wrangler deploy <path>`) under `sanitizedArgs.path`, so we can understand whether people pass a file, a directory, or a relational reference such as `.` or `../example`. The possible values are `file`, `directory`, `current-dir`, `parent-relative`, and `not-found`, or `null` when no positional is provided. The raw path is never sent — only the category.
diff --git a/packages/wrangler/src/__tests__/deploy/entry-points.test.ts b/packages/wrangler/src/__tests__/deploy/entry-points.test.ts
index e3d3a6cd05..594d3e18ea 100644
--- a/packages/wrangler/src/__tests__/deploy/entry-points.test.ts
+++ b/packages/wrangler/src/__tests__/deploy/entry-points.test.ts
@@ -11,6 +11,7 @@ import * as esbuild from "esbuild";
 import { http, HttpResponse } from "msw";
 import dedent from "ts-dedent";
 import { afterEach, assert, beforeEach, describe, it, vi } from "vitest";
+import { logger } from "../../logger";
 import { clearOutputFilePath } from "../../output";
 import { mockAccountId, mockApiToken } from "../helpers/mock-account-id";
 import { mockConsoleMethods } from "../helpers/mock-console";
@@ -1275,4 +1276,71 @@ addEventListener('fetch', event => {});`
 			});
 		});
 	});
+
+	describe("positional path telemetry categorisation", () => {
+		beforeEach(() => {
+			logger.loggerLevel = "debug";
+		});
+		afterEach(() => {
+			logger.resetLoggerLevel();
+		});
+
+		it("records null when no positional is passed", async ({ expect }) => {
+			writeWranglerConfig({ main: "index.js" });
+			fs.writeFileSync("index.js", "export default {};");
+
+			await runWrangler("deploy --dry-run --outdir out");
+
+			expect(std.debug).toContain('"sanitizedCommand":"deploy"');
+			expect(std.debug).toContain('"path":null');
+		});
+
+		it("categorises a file entry-point as 'file'", async ({ expect }) => {
+			writeWranglerConfig();
+			fs.writeFileSync("index.js", "export default {};");
+
+			await runWrangler("deploy index.js --dry-run --outdir out");
+
+			expect(std.debug).toContain('"sanitizedCommand":"deploy"');
+			expect(std.debug).toContain('"path":"file"');
+			// The raw path is never sent in the categorised property.
+			expect(std.debug).not.toContain('"path":"index.js"');
+		});
+
+		it("categorises a directory as 'directory'", async ({ expect }) => {
+			writeWranglerConfig({ name: "test-name" });
+			fs.mkdirSync("public");
+			fs.writeFileSync("public/index.html", "<h1>Hello</h1>");
+
+			await runWrangler("deploy public --dry-run --outdir out --no-autoconfig");
+
+			expect(std.debug).toContain('"path":"directory"');
+		});
+
+		it("categorises the current directory reference as 'current-dir'", async ({
+			expect,
+		}) => {
+			writeWranglerConfig({ name: "test-name" });
+			fs.writeFileSync("index.html", "<h1>Hello</h1>");
+
+			await runWrangler("deploy . --dry-run --outdir out --no-autoconfig");
+
+			expect(std.debug).toContain('"path":"current-dir"');
+		});
+
+		it("categorises a parent-relative reference as 'parent-relative'", async ({
+			expect,
+		}) => {
+			writeWranglerConfig();
+
+			// The path does not need to resolve — the started event (which fires
+			// before the handler) already carries the category. The handler then
+			// fails because the entry-point cannot be found.
+			await expect(
+				runWrangler("deploy ../missing-entry.js --dry-run --outdir out")
+			).rejects.toThrow();
+
+			expect(std.debug).toContain('"path":"parent-relative"');
+		});
+	});
 });
diff --git a/packages/wrangler/src/__tests__/metrics/sanitization.test.ts b/packages/wrangler/src/__tests__/metrics/sanitization.test.ts
index bb5307d905..a06e0ad3d6 100644
--- a/packages/wrangler/src/__tests__/metrics/sanitization.test.ts
+++ b/packages/wrangler/src/__tests__/metrics/sanitization.test.ts
@@ -1,6 +1,10 @@
+import * as fs from "node:fs";
+import { runInTempDir } from "@cloudflare/workers-utils/test-helpers";
 import { describe, it } from "vitest";
 import {
 	ALLOW,
+	categoriseArgs,
+	categorisePositionalPath,
 	COMMAND_ARG_ALLOW_LIST,
 	getAllowedArgs,
 	REDACT,
@@ -136,6 +140,92 @@ describe("getAllowedArgs", () => {
 	});
 });
 
+describe("categorisePositionalPath", () => {
+	runInTempDir();
+
+	it("returns null when no value is provided", ({ expect }) => {
+		expect(categorisePositionalPath(undefined)).toBeNull();
+		expect(categorisePositionalPath("")).toBeNull();
+		expect(categorisePositionalPath(123)).toBeNull();
+	});
+
+	it("categorises the current directory reference", ({ expect }) => {
+		expect(categorisePositionalPath(".")).toBe("current-dir");
+		expect(categorisePositionalPath("./")).toBe("current-dir");
+	});
+
+	it("categorises parent-relative references", ({ expect }) => {
+		expect(categorisePositionalPath("..")).toBe("parent-relative");
+		expect(categorisePositionalPath("../example")).toBe("parent-relative");
+		expect(categorisePositionalPath("../../dist")).toBe("parent-relative");
+	});
+
+	it("categorises an existing directory", ({ expect }) => {
+		fs.mkdirSync("./public");
+		expect(categorisePositionalPath("./public")).toBe("directory");
+		expect(categorisePositionalPath("public")).toBe("directory");
+	});
+
+	it("categorises an existing file", ({ expect }) => {
+		fs.writeFileSync("./index.js", "export default {};");
+		expect(categorisePositionalPath("./index.js")).toBe("file");
+		expect(categorisePositionalPath("index.js")).toBe("file");
+	});
+
+	it("categorises a path that does not exist as not-found", ({ expect }) => {
+		expect(categorisePositionalPath("does-not-exist")).toBe("not-found");
+		expect(categorisePositionalPath("src/missing.ts")).toBe("not-found");
+	});
+});
+
+describe("categoriseArgs", () => {
+	runInTempDir();
+
+	it("only categorises args whose allow-list entry is a categoriser", ({
+		expect,
+	}) => {
+		fs.mkdirSync("./public");
+		const allowedArgs: AllowedArgs = {
+			path: categorisePositionalPath,
+			force: ALLOW,
+			config: REDACT,
+		};
+		const result = categoriseArgs(
+			{ path: "./public", force: true, config: "wrangler.toml" },
+			allowedArgs
+		);
+		expect(result).toEqual({ path: "directory" });
+	});
+
+	it("reads positional values straight from the full args object", ({
+		expect,
+	}) => {
+		// `path` here mirrors the positional set by yargs, which sanitizeArgKeys
+		// would otherwise drop because it is not passed as `--path` in argv.
+		const result = categoriseArgs(
+			{ path: "../example" },
+			{ path: categorisePositionalPath }
+		);
+		expect(result).toEqual({ path: "parent-relative" });
+	});
+
+	it("records null when a positional is absent", ({ expect }) => {
+		const result = categoriseArgs(
+			{ path: undefined },
+			{ path: categorisePositionalPath }
+		);
+		expect(result).toEqual({ path: null });
+	});
+
+	it("omits args when the categoriser returns undefined", ({ expect }) => {
+		const result = categoriseArgs(
+			{ path: "anything" },
+			{ path: () => undefined }
+		);
+		expect(result).toEqual({});
+	});
+});
+
 describe("COMMAND_ARG_ALLOW_LIST", () => {
 	it("should pass boolean flag values through the full sanitisation pipeline for any command", ({
 		expect,
diff --git a/packages/wrangler/src/__tests__/versions/versions.upload.test.ts b/packages/wrangler/src/__tests__/versions/versions.upload.test.ts
index 1230b67a25..886e42c07b 100644
--- a/packages/wrangler/src/__tests__/versions/versions.upload.test.ts
+++ b/packages/wrangler/src/__tests__/versions/versions.upload.test.ts
@@ -16,6 +16,7 @@ import { http, HttpResponse } from "msw";
  * TODO: remove this `expect` import
  */
 import { beforeEach, describe, expect, it, test, vi } from "vitest";
+import { logger } from "../../logger";
 import * as metrics from "../../metrics";
 import { dedent } from "../../utils/dedent";
 import { makeApiRequestAsserter } from "../helpers/assert-request";
@@ -1746,6 +1747,23 @@ describe("versions upload", () => {
 			expect(std.out).toContain("MY_KV");
 			expect(std.out).toContain("--dry-run: exiting now.");
 		});
+
+		test("categorises the positional path in command telemetry", async ({
+			expect,
+		}) => {
+			logger.loggerLevel = "debug";
+			writeWranglerConfig({ name: "test-name" });
+			writeWorkerSource();
+
+			try {
+				await runWrangler("versions upload index.js --dry-run");
+			} finally {
+				logger.resetLoggerLevel();
+			}
+
+			expect(std.debug).toContain('"sanitizedCommand":"versions upload"');
+			expect(std.debug).toContain('"path":"file"');
+		});
 	});
 
 	// --no-bundle, --var/--define/--alias, annotations, non-versioned fields,
diff --git a/packages/wrangler/src/core/register-yargs-command.ts b/packages/wrangler/src/core/register-yargs-command.ts
index 00842a5d9b..e5adc5a6c0 100644
--- a/packages/wrangler/src/core/register-yargs-command.ts
+++ b/packages/wrangler/src/core/register-yargs-command.ts
@@ -27,6 +27,7 @@ import { isNonInteractiveOrCI } from "../is-interactive";
 import { logger } from "../logger";
 import { getMetricsDispatcher } from "../metrics";
 import {
+	categoriseArgs,
 	COMMAND_ARG_ALLOW_LIST,
 	getAllowedArgs,
 	sanitizeArgKeys,
@@ -295,10 +296,12 @@ function createHandler(def: InternalCommandDefinition, argv: string[]) {
 					sanitizedCommand
 				);
 				const argsWithSanitizedKeys = sanitizeArgKeys(args, argv);
-				const sanitizedArgs = sanitizeArgValues(
-					argsWithSanitizedKeys,
-					allowedArgs
-				);
+				const sanitizedArgs = {
+					...sanitizeArgValues(argsWithSanitizedKeys, allowedArgs),
+					// Categorised positional args (e.g. the deploy path) are added
+					// separately because positionals are excluded by sanitizeArgKeys.
+					...categoriseArgs(args, allowedArgs),
+				};
 				const argsUsed = Object.keys(argsWithSanitizedKeys).sort();
 
 				dispatcher.sendCommandEvent(
diff --git a/packages/wrangler/src/metrics/sanitization.ts b/packages/wrangler/src/metrics/sanitization.ts
index 12e086b002..a4e27a4f46 100644
--- a/packages/wrangler/src/metrics/sanitization.ts
+++ b/packages/wrangler/src/metrics/sanitization.ts
@@ -1,3 +1,4 @@
+import { statSync } from "node:fs";
 import { UserError } from "@cloudflare/workers-utils";
 import { getErrorType } from "../core/handle-errors";
 
@@ -30,11 +31,51 @@ export function sanitizeArgKeys(
 export const REDACT = Symbol("REDACT");
 /** Allow all values for this arg. */
 export const ALLOW = Symbol("ALLOW");
+/**
+ * Transform this arg's value into a coarse, non-identifying category label
+ * instead of logging it raw. Return `null` to record that the arg was absent,
+ * or `undefined` to omit the arg entirely.
+ *
+ * Categorisers are the safe way to gather telemetry about high-cardinality or
+ * potentially sensitive values (such as file paths) — only the returned label
+ * is ever sent, never the original value. Unlike the other allow-list values,
+ * categorisers are also applied to positional args (see `categoriseArgs`).
+ */
+export type Categoriser = (value: unknown) => string | null | undefined;
 export type AllowedArgs = {
-	[arg: string]: unknown[] | typeof REDACT | typeof ALLOW;
+	[arg: string]: unknown[] | typeof REDACT | typeof ALLOW | Categoriser;
 };
 export type AllowList = Record<string, AllowedArgs>;
 
+/**
+ * Categorises a positional path argument (e.g. the entry-point or assets path
+ * passed to `wrangler deploy` / `wrangler versions upload`) into a coarse,
+ * non-identifying label.
+ *
+ * The raw value is never returned — paths can leak sensitive information and
+ * are too high-cardinality to analyse. Relational references (`.`, `..`) are
+ * surfaced as their own categories; anything else is resolved against the
+ * filesystem to distinguish files from directories, mirroring how the deploy
+ * path positional is actually interpreted. Returns `null` when no positional
+ * was provided so the property is always present in telemetry.
+ */
+export function categorisePositionalPath(value: unknown): string | null {
+	if (typeof value !== "string" || value.length === 0) {
+		return null;
+	}
+	if (value === "." || value === "./" || value === ".\\") {
+		return "current-dir";
+	}
+	if (value === ".." || value.startsWith("../") || value.startsWith("..\\")) {
+		return "parent-relative";
+	}
+	try {
+		return statSync(value).isDirectory() ? "directory" : "file";
+	} catch {
+		return "not-found";
+	}
+}
+
 /**
  * A list of all the command args that are allowed.
  *
@@ -42,10 +83,12 @@ export type AllowList = Record<string, AllowedArgs>;
  * The top level "*" applies to all commands.
  * Specific commands can override or add to the allow list.
  *
- * Each arg can have one of three values:
+ * Each arg can have one of four values:
  * - an array of strings: only those specific values are allowed
  * - REDACT: the arg value will always be redacted
  * - ALLOW: all values for that arg are allowed
+ * - a Categoriser function: the value is transformed into a coarse category
+ *   label (also applied to positional args)
  */
 export const COMMAND_ARG_ALLOW_LIST: AllowList = {
 	// * applies to all commands.
@@ -98,6 +141,12 @@ export const COMMAND_ARG_ALLOW_LIST: AllowList = {
 	},
 	deploy: {
 		containersRollout: ["immediate", "gradual"],
+		// Categorise the entry-point/assets positional without logging the raw path.
+		path: categorisePositionalPath,
+	},
+	"versions upload": {
+		// `versions upload` shares the same positional path semantics as `deploy`.
+		path: categorisePositionalPath,
 	},
 };
 
@@ -155,6 +204,33 @@ export function sanitizeArgValues(
 	return result;
 }
 
+/**
+ * Applies categoriser transforms from the allow-list to the raw args.
+ *
+ * Unlike {@link sanitizeArgValues}, this reads from the *full* args object
+ * rather than the argv-filtered set produced by {@link sanitizeArgKeys}. That
+ * is what allows positional args — which are otherwise deliberately excluded
+ * from telemetry — to be safely categorised into a fixed label. Only args whose
+ * allow-list entry is a {@link Categoriser} are considered, and only the label
+ * it returns (never the raw value) is emitted. A `null` result is recorded as-is
+ * (the arg was absent); an `undefined` result omits the arg entirely.
+ */
+export function categoriseArgs(
+	args: Record<string, unknown>,
+	allowedArgs: AllowedArgs
+): Record<string, string | null> {
+	const result: Record<string, string | null> = {};
+	for (const [key, allowed] of Object.entries(allowedArgs)) {
+		if (typeof allowed === "function") {
+			const category = allowed(args[key]);
+			if (category !== undefined) {
+				result[key] = category;
+			}
+		}
+	}
+	return result;
+}
+
 /**
  * Returns the canonical argument name for metrics reporting.
  */
diff --git a/packages/wrangler/src/metrics/types.ts b/packages/wrangler/src/metrics/types.ts
index 88c64f8e7d..fbdf75fdf3 100644
--- a/packages/wrangler/src/metrics/types.ts
+++ b/packages/wrangler/src/metrics/types.ts
@@ -103,6 +103,12 @@ type CommandEventProperties = CommonCommandEventProperties & {
 	 * the sanitized args would only contain `{ format: "json" }` since that is the only allowed value.
 	 * The `<key>` positional argument and `--namespace-id` flag would be omitted since they are not allowed.
 	 *
+	 * Positional args are normally excluded entirely, but an allow-list entry may
+	 * define a categoriser that maps a positional value to a coarse, non-identifying
+	 * label (never the raw value). For example, `wrangler deploy ./dist` records
+	 * `{ path: "directory" }`, while `wrangler deploy` with no positional records
+	 * `{ path: null }`.
+	 *
 	 * It is named `sanitizedArgs` to distinguish it from the historical `args` field which
 	 * may have contained sensitive data in older Wrangler versions.
 	 */