diff --git a/lib/src/index.ts b/lib/src/index.ts
index 5e7c508..e934cc7 100644
--- a/lib/src/index.ts
+++ b/lib/src/index.ts
@@ -10,6 +10,7 @@ import initAPIToken from "./services/apiToken/initAPIToken";
 import { initProjectConfig } from "./services/projectConfig";
 import appContext from "./utils/appContext";
 import type commander from "commander";
+import { ErrorType, isDittoError, isDittoErrorType } from "./utils/DittoError";
 
 type Command = "pull";
 
@@ -87,18 +88,33 @@ const executeCommand = async (
       }
     }
   } catch (error) {
-    const eventId = Sentry.captureException(error);
-    const eventStr = `\n\nError ID: ${logger.info(eventId)}`;
-
     if (process.env.DEBUG === "true") {
       console.error(logger.info("Development stack trace:\n"), error);
     }
 
-    return await quit(
-      logger.errorText(
-        "Something went wrong. Please contact support or try again later."
-      ) + eventStr
-    );
+    let sentryOptions = undefined;
+    let exitCode = undefined;
+    let errorText =
+      "Something went wrong. Please contact support or try again later.";
+
+    if (isDittoError(error)) {
+      exitCode = error.exitCode;
+
+      if (isDittoErrorType(error, ErrorType.ConfigYamlLoadError)) {
+        errorText = error.message;
+      } else if (isDittoErrorType(error, ErrorType.ConfigParseError)) {
+        errorText = `${error.data.messagePrefix}\n\n${error.data.formattedError}`;
+      }
+
+      sentryOptions = {
+        extra: { message: errorText, ...(error.data || {}) },
+      };
+    }
+
+    const eventId = Sentry.captureException(error, sentryOptions);
+    const eventStr = `\n\nError ID: ${logger.info(eventId)}`;
+
+    return await quit(logger.errorText(errorText) + eventStr, exitCode);
   }
 };
 
diff --git a/lib/src/outputs/json.ts b/lib/src/outputs/json.ts
index 21edefd..ab544ab 100644
--- a/lib/src/outputs/json.ts
+++ b/lib/src/outputs/json.ts
@@ -4,12 +4,12 @@ import { ZBaseOutputFilters } from "./shared";
 const ZBaseJSONOutput = ZBaseOutputFilters.extend({
   format: z.literal("json"),
   framework: z.undefined(),
-});
+}).strict();
 
 const Zi18NextJSONOutput = ZBaseJSONOutput.extend({
   framework: z.literal("i18next"),
   type: z.literal("module").or(z.literal("commonjs")).optional(),
-});
+}).strict();
 
 export const ZJSONOutput = z.discriminatedUnion("framework", [
   ZBaseJSONOutput,
diff --git a/lib/src/services/projectConfig.ts b/lib/src/services/projectConfig.ts
index 713b35b..d18fe9d 100644
--- a/lib/src/services/projectConfig.ts
+++ b/lib/src/services/projectConfig.ts
@@ -5,6 +5,7 @@ import appContext from "../utils/appContext";
 import yaml from "js-yaml";
 import { ZBaseOutputFilters } from "../outputs/shared";
 import { ZOutput } from "../outputs";
+import DittoError, { ErrorType } from "../utils/DittoError";
 
 const ZProjectConfigYAML = ZBaseOutputFilters.extend({
   outputs: z.array(ZOutput),
@@ -38,12 +39,30 @@ function readProjectConfigData(
   file = appContext.projectConfigFile,
   defaultData: ProjectConfigYAML = DEFAULT_PROJECT_CONFIG_JSON
 ): ProjectConfigYAML {
-  createFileIfMissingSync(file, yaml.dump(defaultData));
-  const fileContents = fs.readFileSync(file, "utf8");
-  const yamlData = yaml.load(fileContents);
+  let yamlData: unknown = defaultData;
+
+  try {
+    createFileIfMissingSync(file, yaml.dump(defaultData));
+    const fileContents = fs.readFileSync(file, "utf8");
+    yamlData = yaml.load(fileContents);
+  } catch (err) {
+    throw new DittoError({
+      type: ErrorType.ConfigYamlLoadError,
+      data: { rawErrorMessage: (err as any).message },
+      message:
+        "Could not load the project config file. Please check the file path and that it is a valid YAML file.",
+    });
+  }
+
   const parsedYAML = ZProjectConfigYAML.safeParse(yamlData);
   if (!parsedYAML.success) {
-    throw new Error("Failed to parse project config file");
+    throw new DittoError({
+      type: ErrorType.ConfigParseError,
+      data: {
+        formattedError: JSON.stringify(parsedYAML.error.flatten(), null, 2),
+        messagePrefix: "There is an error in your project config file.",
+      },
+    });
   }
   return parsedYAML.data;
 }
diff --git a/lib/src/utils/DittoError.ts b/lib/src/utils/DittoError.ts
new file mode 100644
index 0000000..31efb44
--- /dev/null
+++ b/lib/src/utils/DittoError.ts
@@ -0,0 +1,81 @@
+import { z } from "zod";
+
+/**
+ * An Error extension designed to be thrown from anywhere in the CLI.
+ * The custom properties provide a reliable way to include additional data
+ * (what the error was and context around it) that can be leveraged
+ * to pass along data to the user, to Sentry, or to other services.
+ */
+export default class DittoError<T extends ErrorType> extends Error {
+  exitCode: number | undefined;
+  type: ErrorType;
+  // Note: if you see the type error "Type 'T' cannot be used to index type 'ErrorDataMap'",
+  // a value is missing from the ErrorDataMap defined below
+  data: ErrorDataMap[T];
+
+  /**
+   * Creates a new custom error with the following properties:
+   * @param type The type of error, from the ErrorType enum
+   * @param message Optional: error message to display to the user
+   * @param exitCode Optional: exit code to return to the shell.
+   * @param data Optional: additional data to pass along with the error
+   */
+  constructor({
+    type,
+    message,
+    exitCode,
+    data,
+  }: {
+    type: T;
+    message?: string;
+    exitCode?: number;
+    data: ErrorDataMap[T];
+  }) {
+    const errorMessage =
+      message ||
+      "Something went wrong. Please contact support or try again later.";
+
+    super(errorMessage);
+
+    this.exitCode = exitCode;
+    this.type = type;
+    this.data = data;
+  }
+}
+
+/**
+ * Exhaustive list of DittoError types
+ * When adding to this list, you must also add a Data type to ErrorDataMap
+ */
+export enum ErrorType {
+  ConfigYamlLoadError = "ConfigYamlLoadError",
+  ConfigParseError = "ConfigParseError",
+}
+
+/**
+ * Map of DittoError types to the data that is required for that type
+ * The keys of this must exhaustively match the keys of the ErrorType enum
+ */
+type ErrorDataMap = {
+  [ErrorType.ConfigYamlLoadError]: ConfigYamlLoadErrorData;
+  [ErrorType.ConfigParseError]: ConfigParseErrorData;
+};
+
+type ConfigYamlLoadErrorData = {
+  rawErrorMessage: string;
+};
+
+type ConfigParseErrorData = {
+  formattedError: string;
+  messagePrefix: string;
+};
+
+export function isDittoError(error: unknown): error is DittoError<ErrorType> {
+  return error instanceof DittoError;
+}
+export function isDittoErrorType<T extends ErrorType>(
+  error: DittoError<ErrorType>,
+  type: T
+): error is DittoError<T> {
+  return error.type === type;
+}