diff --git a/.changeset/old-teachers-bow.md b/.changeset/old-teachers-bow.md
new file mode 100644
index 000000000000..c7eb420a2a18
--- /dev/null
+++ b/.changeset/old-teachers-bow.md
@@ -0,0 +1,7 @@
+---
+"wrangler": minor
+---
+
+feat: add sanitised error messages to Wrangler telemetry
+
+Error messages that have been audited for potential inclusion of personal information, and explicitly opted-in, are now included in Wrangler's telemetry collection. Collected error messages will not include any filepaths, user input or any other potentially private content.
diff --git a/packages/wrangler/src/__tests__/errors.test.ts b/packages/wrangler/src/__tests__/errors.test.ts
new file mode 100644
index 000000000000..8cec76ebf27a
--- /dev/null
+++ b/packages/wrangler/src/__tests__/errors.test.ts
@@ -0,0 +1,135 @@
+import {
+	CommandLineArgsError,
+	DeprecationError,
+	FatalError,
+	MissingConfigError,
+	UserError,
+} from "../errors";
+import { APIError, ParseError } from "../parse";
+
+describe("errors", () => {
+	describe("UserError", () => {
+		it("takes a custom telemetry message", () => {
+			const error = new UserError("message", { telemetryMessage: "telemetry" });
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("telemetry");
+		});
+		it("can set telemetryMessage to equal the main message", () => {
+			const error = new UserError("message", { telemetryMessage: true });
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("message");
+		});
+	});
+
+	describe("DeprecationError", () => {
+		it("takes a custom telemetry message", () => {
+			const error = new DeprecationError("message", {
+				telemetryMessage: "telemetry",
+			});
+			expect(error.message).toBe("Deprecation:\nmessage");
+			expect(error.telemetryMessage).toBe("telemetry");
+		});
+		it("can set telemetryMessage to equal the main message", () => {
+			const error = new DeprecationError("message", { telemetryMessage: true });
+			expect(error.message).toBe("Deprecation:\nmessage");
+			expect(error.telemetryMessage).toBe("Deprecation:\nmessage");
+		});
+	});
+
+	describe("FatalError", () => {
+		it("takes a custom telemetry message", () => {
+			const error = new FatalError("message", undefined, {
+				telemetryMessage: "telemetry",
+			});
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("telemetry");
+			expect(error.code).toBeUndefined();
+		});
+		it("can set telemetryMessage to equal the main message", () => {
+			const error = new FatalError("message", 1, { telemetryMessage: true });
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("message");
+			expect(error.code).toBe(1);
+		});
+	});
+
+	describe("CommandLineArgsError", () => {
+		it("takes a custom telemetry message", () => {
+			const error = new CommandLineArgsError("message", {
+				telemetryMessage: "telemetry",
+			});
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("telemetry");
+		});
+		it("can set telemetryMessage to equal the main message", () => {
+			const error = new CommandLineArgsError("message", {
+				telemetryMessage: true,
+			});
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("message");
+		});
+	});
+
+	describe("JsonFriendlyFatalError", () => {
+		it("takes a custom telemetry message", () => {
+			const error = new FatalError("message", undefined, {
+				telemetryMessage: "telemetry",
+			});
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("telemetry");
+			expect(error.code).toBeUndefined();
+		});
+		it("can set telemetryMessage to equal the main message", () => {
+			const error = new FatalError("message", 1, { telemetryMessage: true });
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("message");
+			expect(error.code).toBe(1);
+		});
+	});
+
+	describe("MissingConfigError", () => {
+		it("just sets the telemetry message as the main message", () => {
+			const error = new MissingConfigError("message");
+			expect(error.message).toBe("Missing config value for message");
+			expect(error.telemetryMessage).toBe("Missing config value for message");
+		});
+	});
+
+	describe("ParseError", () => {
+		it("takes a custom telemetry message", () => {
+			const error = new ParseError({
+				text: "message",
+				telemetryMessage: "telemetry",
+			});
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("telemetry");
+		});
+		it("can set telemetryMessage to equal the main message", () => {
+			const error = new ParseError({
+				text: "message",
+				telemetryMessage: true,
+			});
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("message");
+		});
+	});
+
+	describe("APIError", () => {
+		it("takes a custom telemetry message", () => {
+			const error = new APIError({
+				text: "message",
+				telemetryMessage: "telemetry",
+			});
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("telemetry");
+		});
+		it("can set telemetryMessage to equal the main message", () => {
+			const error = new APIError({
+				text: "message",
+				telemetryMessage: true,
+			});
+			expect(error.message).toBe("message");
+			expect(error.telemetryMessage).toBe("message");
+		});
+	});
+});
diff --git a/packages/wrangler/src/__tests__/metrics.test.ts b/packages/wrangler/src/__tests__/metrics.test.ts
index d0b5ac3d18b9..2b995223470f 100644
--- a/packages/wrangler/src/__tests__/metrics.test.ts
+++ b/packages/wrangler/src/__tests__/metrics.test.ts
@@ -321,6 +321,7 @@ describe("metrics", () => {
 						durationSeconds: 6,
 						durationMinutes: 0.1,
 						errorType: "TypeError",
+						errorMessage: undefined,
 					},
 				};
 
@@ -445,6 +446,34 @@ describe("metrics", () => {
 				expect(std.debug).toContain('"isInteractive":false,');
 			});
 
+			it("should include an error message if the specific error has been allow-listed with {telemetryMessage:true}", async () => {
+				setIsTTY(false);
+				const requests = mockMetricRequest();
+
+				await expect(
+					runWrangler("docs arg -j=false")
+				).rejects.toThrowErrorMatchingInlineSnapshot(
+					`[Error: Wrangler now supports wrangler.json configuration files by default and ignores the value of the \`--experimental-json-config\` flag.]`
+				);
+				expect(requests.count).toBe(2);
+				expect(std.debug).toContain(
+					'"errorMessage":"Wrangler now supports wrangler.json configuration files by default and ignores the value of the `--experimental-json-config` flag."'
+				);
+			});
+
+			it("should include an error message if the specific error has been allow-listed with a custom telemetry message", async () => {
+				setIsTTY(false);
+				const requests = mockMetricRequest();
+
+				await expect(
+					runWrangler("bloop")
+				).rejects.toThrowErrorMatchingInlineSnapshot(
+					`[Error: Unknown argument: bloop]`
+				);
+				expect(requests.count).toBe(2);
+				expect(std.debug).toContain('"errorMessage":"yargs validation error"');
+			});
+
 			describe("banner", () => {
 				beforeEach(() => {
 					vi.mocked(getWranglerVersion).mockReturnValue("1.2.3");
diff --git a/packages/wrangler/src/__tests__/parse.test.ts b/packages/wrangler/src/__tests__/parse.test.ts
index b87828136ec3..88d21ad5f99f 100644
--- a/packages/wrangler/src/__tests__/parse.test.ts
+++ b/packages/wrangler/src/__tests__/parse.test.ts
@@ -142,6 +142,7 @@ describe("parseTOML", () => {
 					lineText: "name = 'fail\"",
 				},
 				notes: [],
+				telemetryMessage: "TOML parse error",
 			});
 		}
 	});
@@ -163,6 +164,7 @@ describe("parseTOML", () => {
 					fileText: "\n[name",
 				},
 				notes: [],
+				telemetryMessage: "TOML parse error",
 			});
 		}
 	});
@@ -232,6 +234,7 @@ describe("parseJSON", () => {
 					fileText: `\n{\n"version" "1\n}\n`,
 				},
 				notes: [],
+				telemetryMessage: "JSON(C) parse error",
 			});
 			expect(text).toEqual("UnexpectedEndOfString");
 		}
@@ -257,6 +260,7 @@ describe("parseJSON", () => {
 					lineText: `\t\t\t"c":[012345]`,
 				},
 				notes: [],
+				telemetryMessage: "JSON(C) parse error",
 			});
 		}
 	});
@@ -339,6 +343,7 @@ describe("parseJSONC", () => {
 					fileText: `\n{\n"version" "1\n}\n`,
 				},
 				notes: [],
+				telemetryMessage: "JSON(C) parse error",
 			});
 		}
 	});
@@ -363,6 +368,7 @@ describe("parseJSONC", () => {
 					lineText: `\t\t\t"c":[012345]`,
 				},
 				notes: [],
+				telemetryMessage: "JSON(C) parse error",
 			});
 		}
 	});
diff --git a/packages/wrangler/src/assets.ts b/packages/wrangler/src/assets.ts
index e22c6e95703e..7df9018404e4 100644
--- a/packages/wrangler/src/assets.ts
+++ b/packages/wrangler/src/assets.ts
@@ -77,7 +77,8 @@ export const syncAssets = async (
 		if (!initializeAssetsResponse.jwt) {
 			throw new FatalError(
 				"Could not find assets information to attach to deployment. Please try again.",
-				1
+				1,
+				{ telemetryMessage: true }
 			);
 		}
 		logger.info(`No files to upload. Proceeding with deployment...`);
@@ -102,7 +103,11 @@ export const syncAssets = async (
 			if (manifestEntry === undefined) {
 				throw new FatalError(
 					`A file was requested that does not appear to exist.`,
-					1
+					1,
+					{
+						telemetryMessage:
+							"A file was requested that does not appear to exist. (asset manifest upload)",
+					}
 				);
 			}
 			// just logging file uploads at the moment...
@@ -182,7 +187,9 @@ export const syncAssets = async (
 					throw new FatalError(
 						`Upload took too long.\n` +
 							`Asset upload took too long on bucket ${bucketIndex + 1}/${initializeAssetsResponse.buckets.length}. Please try again.\n` +
-							`Assets already uploaded have been saved, so the next attempt will automatically resume from this point.`
+							`Assets already uploaded have been saved, so the next attempt will automatically resume from this point.`,
+						undefined,
+						{ telemetryMessage: "Asset upload took too long" }
 					);
 				} else {
 					throw e;
@@ -207,7 +214,8 @@ export const syncAssets = async (
 	if (!completionJwt) {
 		throw new FatalError(
 			"Failed to complete asset upload. Please try again.",
-			1
+			1,
+			{ telemetryMessage: true }
 		);
 	}
 
@@ -249,7 +257,8 @@ const buildAssetManifest = async (dir: string) => {
 					throw new UserError(
 						`Maximum number of assets exceeded.\n` +
 							`Cloudflare Workers supports up to ${MAX_ASSET_COUNT.toLocaleString()} assets in a version. We found ${counter.toLocaleString()} files in the specified assets directory "${dir}".\n` +
-							`Ensure your assets directory contains a maximum of ${MAX_ASSET_COUNT.toLocaleString()} files, and that you have specified your assets directory correctly.`
+							`Ensure your assets directory contains a maximum of ${MAX_ASSET_COUNT.toLocaleString()} files, and that you have specified your assets directory correctly.`,
+						{ telemetryMessage: "Maximum number of assets exceeded" }
 					);
 				}
 
@@ -267,7 +276,8 @@ const buildAssetManifest = async (dir: string) => {
 									binary: true,
 								}
 							)}.\n` +
-							`Ensure all assets in your assets directory "${dir}" conform with the Workers maximum size requirement.`
+							`Ensure all assets in your assets directory "${dir}" conform with the Workers maximum size requirement.`,
+						{ telemetryMessage: "Asset too large" }
 					);
 				}
 				manifest[normalizeFilePath(relativeFilepath)] = {
@@ -335,12 +345,15 @@ export function getAssetsOptions(
 
 	if (directory === undefined) {
 		throw new UserError(
-			"The `assets` property in your configuration is missing the required `directory` property."
+			"The `assets` property in your configuration is missing the required `directory` property.",
+			{ telemetryMessage: true }
 		);
 	}
 
 	if (directory === "") {
-		throw new UserError("`The assets directory cannot be an empty string.");
+		throw new UserError("`The assets directory cannot be an empty string.", {
+			telemetryMessage: true,
+		});
 	}
 
 	const assetsBasePath = getAssetsBasePath(config, args.assets);
@@ -353,7 +366,11 @@ export function getAssetsOptions(
 
 		throw new UserError(
 			`The directory specified by the ${sourceOfTruthMessage} does not exist:\n` +
-				`${resolvedAssetsPath}`
+				`${resolvedAssetsPath}`,
+
+			{
+				telemetryMessage: `The assets directory specified does not exist`,
+			}
 		);
 	}
 
@@ -413,7 +430,11 @@ export function validateAssetsArgsAndConfig(
 	) {
 		throw new UserError(
 			"Cannot use assets and legacy assets in the same Worker.\n" +
-				"Please remove either the `legacy_assets` or `assets` field from your configuration file."
+				"Please remove either the `legacy_assets` or `assets` field from your configuration file.",
+			{
+				telemetryMessage:
+					"Cannot use assets and legacy assets in the same Worker",
+			}
 		);
 	}
 
@@ -440,7 +461,8 @@ export function validateAssetsArgsAndConfig(
 	) {
 		throw new UserError(
 			"Cannot use assets with a binding in an assets-only Worker.\n" +
-				"Please remove the asset binding from your configuration file, or provide a Worker script in your configuration file (`main`)."
+				"Please remove the asset binding from your configuration file, or provide a Worker script in your configuration file (`main`).",
+			{ telemetryMessage: true }
 		);
 	}
 
@@ -481,7 +503,8 @@ export function validateAssetsArgsAndConfig(
 	) {
 		throw new UserError(
 			"Cannot set experimental_serve_directly=false without a Worker script.\n" +
-				"Please remove experimental_serve_directly from your configuration file, or provide a Worker script in your configuration file (`main`)."
+				"Please remove experimental_serve_directly from your configuration file, or provide a Worker script in your configuration file (`main`).",
+			{ telemetryMessage: true }
 		);
 	}
 }
@@ -526,12 +549,15 @@ function errorOnLegacyPagesWorkerJSAsset(
 					? "directory"
 					: null;
 		if (workerJsType !== null) {
-			throw new UserError(dedent`
+			throw new UserError(
+				dedent`
 			Uploading a Pages _worker.js ${workerJsType} as an asset.
 			This could expose your private server-side code to the public Internet. Is this intended?
 			If you do not want to upload this ${workerJsType}, either remove it or add an "${CF_ASSETS_IGNORE_FILENAME}" file, to the root of your asset directory, containing "_worker.js" to avoid uploading.
 			If you do want to upload this ${workerJsType}, you can add an empty "${CF_ASSETS_IGNORE_FILENAME}" file, to the root of your asset directory, to hide this error.
-		`);
+		`,
+				{ telemetryMessage: true }
+			);
 		}
 	}
 }
diff --git a/packages/wrangler/src/d1/execute.ts b/packages/wrangler/src/d1/execute.ts
index 24d76c5c8651..f9fcd8071af8 100644
--- a/packages/wrangler/src/d1/execute.ts
+++ b/packages/wrangler/src/d1/execute.ts
@@ -116,7 +116,9 @@ export const Handler = async (args: HandlerOptions): Promise<void> => {
 	if (file && command) {
 		throw createFatalError(
 			`Error: can't provide both --command and --file.`,
-			json
+			json,
+			undefined,
+			{ telemetryMessage: true }
 		);
 	}
 
diff --git a/packages/wrangler/src/delete.ts b/packages/wrangler/src/delete.ts
index 6a05069d29f8..5f074ba2eaa1 100644
--- a/packages/wrangler/src/delete.ts
+++ b/packages/wrangler/src/delete.ts
@@ -98,7 +98,8 @@ export async function deleteHandler(args: DeleteArgs) {
 	if (config.pages_build_output_dir) {
 		throw new UserError(
 			"It looks like you've run a Workers-specific command in a Pages project.\n" +
-				"For Pages, please run `wrangler pages project delete` instead."
+				"For Pages, please run `wrangler pages project delete` instead.",
+			{ telemetryMessage: true }
 		);
 	}
 	metrics.sendMetricsEvent(
@@ -112,7 +113,11 @@ export async function deleteHandler(args: DeleteArgs) {
 	const scriptName = getScriptName(args, config);
 	if (!scriptName) {
 		throw new UserError(
-			`A worker name must be defined, either via --name, or in your ${configFileName(config.configPath)} file`
+			`A worker name must be defined, either via --name, or in your ${configFileName(config.configPath)} file`,
+			{
+				telemetryMessage:
+					"`A worker name must be defined, either via --name, or in your config file",
+			}
 		);
 	}
 
diff --git a/packages/wrangler/src/deployments.ts b/packages/wrangler/src/deployments.ts
index 999b81e30184..106592d55647 100644
--- a/packages/wrangler/src/deployments.ts
+++ b/packages/wrangler/src/deployments.ts
@@ -157,13 +157,16 @@ export async function rollbackDeployment(
 
 		if (deploys.length < 2) {
 			throw new UserError(
-				"Cannot rollback to previous deployment since there are less than 2 deployments"
+				"Cannot rollback to previous deployment since there are less than 2 deployments",
+				{ telemetryMessage: true }
 			);
 		}
 
 		deploymentId = deploys.at(-2)?.id;
 		if (deploymentId === undefined) {
-			throw new UserError("Cannot find previous deployment");
+			throw new UserError("Cannot find previous deployment", {
+				telemetryMessage: true,
+			});
 		}
 	}
 
@@ -265,7 +268,9 @@ export async function viewDeployment(
 
 		deploymentId = latest.id;
 		if (deploymentId === undefined) {
-			throw new UserError("Cannot find previous deployment");
+			throw new UserError("Cannot find previous deployment", {
+				telemetryMessage: true,
+			});
 		}
 	}
 
@@ -333,7 +338,10 @@ export async function commonDeploymentCMDSetup(
 
 	if (!scriptName) {
 		throw new UserError(
-			`Required Worker name missing. Please specify the Worker name in your ${configFileName(config.configPath)} file, or pass it as an argument with \`--name\``
+			`Required Worker name missing. Please specify the Worker name in your ${configFileName(config.configPath)} file, or pass it as an argument with \`--name\``,
+			{
+				telemetryMessage: `Required Worker name missing. Please specify the Worker name in your config file, or pass it as an argument with \`--name\``,
+			}
 		);
 	}
 
diff --git a/packages/wrangler/src/dialogs.ts b/packages/wrangler/src/dialogs.ts
index f8ecba8a4cf2..8c47c0caf8f2 100644
--- a/packages/wrangler/src/dialogs.ts
+++ b/packages/wrangler/src/dialogs.ts
@@ -9,7 +9,9 @@ export class NoDefaultValueProvided extends UserError {
 		// This is user-facing, so make the message something understandable
 		// It _should_ always be caught and replaced with a more descriptive error
 		// but this is fine as a fallback.
-		super("This command cannot be run in a non-interactive context");
+		super("This command cannot be run in a non-interactive context", {
+			telemetryMessage: true,
+		});
 		Object.setPrototypeOf(this, new.target.prototype);
 	}
 }
diff --git a/packages/wrangler/src/errors.ts b/packages/wrangler/src/errors.ts
index e273d9572c98..509ff98b1909 100644
--- a/packages/wrangler/src/errors.ts
+++ b/packages/wrangler/src/errors.ts
@@ -1,3 +1,11 @@
+/**
+ * This is used to provide telemetry with a sanitised error
+ * message that could not have any user-identifying information.
+ * Set to `true` to duplicate `message`.
+ *  */
+export type TelemetryMessage = {
+	telemetryMessage?: string | true;
+};
 /**
  * Base class for errors where the user has done something wrong. These are not
  * reported to Sentry. API errors are intentionally *not* `UserError`s, and are
@@ -5,26 +13,33 @@
  * messaging.
  */
 export class UserError extends Error {
-	constructor(...args: ConstructorParameters<typeof Error>) {
-		super(...args);
+	telemetryMessage: string | undefined;
+	constructor(
+		message?: string | undefined,
+		options?: (ErrorOptions & TelemetryMessage) | undefined
+	) {
+		super(message, options);
 		// Restore prototype chain:
 		// https://www.typescriptlang.org/docs/handbook/release-notes/typescript-2-2.html#support-for-newtarget
 		Object.setPrototypeOf(this, new.target.prototype);
+		this.telemetryMessage =
+			options?.telemetryMessage === true ? message : options?.telemetryMessage;
 	}
 }
 
 export class DeprecationError extends UserError {
-	constructor(message: string) {
-		super(`Deprecation:\n${message}`);
+	constructor(message: string, options?: TelemetryMessage) {
+		super(`Deprecation:\n${message}`, options);
 	}
 }
 
 export class FatalError extends UserError {
 	constructor(
 		message?: string,
-		readonly code?: number
+		readonly code?: number | undefined,
+		options?: TelemetryMessage
 	) {
-		super(message);
+		super(message, options);
 	}
 }
 
@@ -41,15 +56,18 @@ export class CommandLineArgsError extends UserError {}
 export class JsonFriendlyFatalError extends FatalError {
 	constructor(
 		message?: string,
-		readonly code?: number
+		readonly code?: number,
+		options?: TelemetryMessage
 	) {
-		super(message);
+		super(message, code, options);
 	}
 }
 
 export class MissingConfigError extends Error {
+	telemetryMessage: string | undefined;
 	constructor(key: string) {
 		super(`Missing config value for ${key}`);
+		this.telemetryMessage = `Missing config value for ${key}`;
 	}
 }
 
@@ -61,11 +79,16 @@ export class MissingConfigError extends Error {
 export function createFatalError(
 	message: unknown,
 	isJson: boolean,
-	code?: number
+	code?: number,
+	telemetryMessage?: TelemetryMessage
 ): Error {
 	if (isJson) {
-		return new JsonFriendlyFatalError(JSON.stringify(message), code);
+		return new JsonFriendlyFatalError(
+			JSON.stringify(message),
+			code,
+			telemetryMessage
+		);
 	} else {
-		return new FatalError(`${message}`, code);
+		return new FatalError(`${message}`, code, telemetryMessage);
 	}
 }
diff --git a/packages/wrangler/src/index.ts b/packages/wrangler/src/index.ts
index 33ce6dec0fa0..db04b6db7490 100644
--- a/packages/wrangler/src/index.ts
+++ b/packages/wrangler/src/index.ts
@@ -206,7 +206,9 @@ export function createCLIParser(argv: string[]) {
 			if (!error || error.name === "YError") {
 				// If there is no error or the error is a "YError", then this came from yargs own validation
 				// Wrap it in a `CommandLineArgsError` so that we can handle it appropriately further up.
-				error = new CommandLineArgsError(msg);
+				error = new CommandLineArgsError(msg, {
+					telemetryMessage: "yargs validation error",
+				});
 			}
 			throw error;
 		})
@@ -254,7 +256,8 @@ export function createCLIParser(argv: string[]) {
 		.check((args) => {
 			if (args["experimental-json-config"] === false) {
 				throw new CommandLineArgsError(
-					`Wrangler now supports wrangler.json configuration files by default and ignores the value of the \`--experimental-json-config\` flag.`
+					`Wrangler now supports wrangler.json configuration files by default and ignores the value of the \`--experimental-json-config\` flag.`,
+					{ telemetryMessage: true }
 				);
 			}
 			return true;
@@ -1143,6 +1146,7 @@ export async function main(argv: string[]): Promise<void> {
 				durationMinutes: durationMs / 1000 / 60,
 				errorType:
 					errorType ?? (e instanceof Error ? e.constructor.name : undefined),
+				errorMessage: e instanceof UserError ? e.telemetryMessage : undefined,
 			},
 			argv
 		);
diff --git a/packages/wrangler/src/metrics/types.ts b/packages/wrangler/src/metrics/types.ts
index 28ebdf2c2396..caa6d694817a 100644
--- a/packages/wrangler/src/metrics/types.ts
+++ b/packages/wrangler/src/metrics/types.ts
@@ -125,5 +125,9 @@ export type Events =
 				 * Type of error, e.g. UserError, APIError. Does not include stack trace or error message.
 				 */
 				errorType: string | undefined;
+				/**
+				 * Sanitised error messages that will not include user information like filepaths or stack traces (e.g. `Asset too large`).
+				 */
+				errorMessage: string | undefined;
 			};
 	  };
diff --git a/packages/wrangler/src/parse.ts b/packages/wrangler/src/parse.ts
index 6e662a0d476d..1e50cb2a4109 100644
--- a/packages/wrangler/src/parse.ts
+++ b/packages/wrangler/src/parse.ts
@@ -5,6 +5,7 @@ import { formatMessagesSync } from "esbuild";
 import * as jsoncParser from "jsonc-parser";
 import { UserError } from "./errors";
 import { logger } from "./logger";
+import type { TelemetryMessage } from "./errors";
 import type { ParseError as JsoncParseError } from "jsonc-parser";
 
 export type Message = {
@@ -12,7 +13,7 @@ export type Message = {
 	location?: Location;
 	notes?: Message[];
 	kind?: "warning" | "error";
-};
+} & TelemetryMessage;
 
 export type Location = File & {
 	line: number;
@@ -56,8 +57,8 @@ export class ParseError extends UserError implements Message {
 	readonly location?: Location;
 	readonly kind: "warning" | "error";
 
-	constructor({ text, notes, location, kind }: Message) {
-		super(text);
+	constructor({ text, notes, location, kind, telemetryMessage }: Message) {
+		super(text, { telemetryMessage });
 		this.name = this.constructor.name;
 		this.text = text;
 		this.notes = notes ?? [];
@@ -132,7 +133,11 @@ export function parseTOML(input: string, file?: string): TOML.JsonMap | never {
 			file,
 			fileText: input,
 		};
-		throw new ParseError({ text, location });
+		throw new ParseError({
+			text,
+			location,
+			telemetryMessage: "TOML parse error",
+		});
 	}
 }
 
@@ -180,6 +185,7 @@ export function parseJSONC(
 				...indexLocation({ file, fileText: input }, errors[0].offset + 1),
 				length: errors[0].length,
 			},
+			telemetryMessage: "JSON(C) parse error",
 		});
 	}
 	return data;
@@ -219,6 +225,7 @@ export function readFileSync(file: string): string {
 					text: message.replace(file, resolve(file)),
 				},
 			],
+			telemetryMessage: "Could not read file",
 		});
 	}
 }
diff --git a/packages/wrangler/src/tail/index.ts b/packages/wrangler/src/tail/index.ts
index a2fdf30b00ae..ee0a5aff703d 100644
--- a/packages/wrangler/src/tail/index.ts
+++ b/packages/wrangler/src/tail/index.ts
@@ -229,7 +229,8 @@ export const tailCommand = createCommand({
 					throw createFatalError(
 						"Tail disconnected, exiting.",
 						args.format === "json",
-						1
+						1,
+						{ telemetryMessage: true }
 					);
 				}
 				waitingForPong = true;
diff --git a/packages/wrangler/telemetry.md b/packages/wrangler/telemetry.md
index 6bf9fd86ff6c..0c867319748a 100644
--- a/packages/wrangler/telemetry.md
+++ b/packages/wrangler/telemetry.md
@@ -21,7 +21,7 @@ Telemetry in Wrangler allows us to better identify bugs and gain visibility on u
 - The format of the Wrangler configuration file (e.g. `toml`, `jsonc`)
 - Total session duration of the command run (e.g. 3 seconds, etc.)
 - Whether the Wrangler client is running in CI or in an interactive instance
-- Error _type_, if one occurs (e.g. `APIError` or `UserError`)
+- Error _type_ (e.g. `APIError` or `UserError`), and sanitised error messages that will not include user information like filepaths or stack traces (e.g. `Asset too large`).
 - General machine information such as OS and OS Version
 
 Cloudflare will receive the IP address associated with your machine and such information is handled in accordance with Cloudflare’s [Privacy Policy](https://www.cloudflare.com/privacypolicy/).