diff --git a/apps/wing/src/cli.ts b/apps/wing/src/cli.ts
index 7083289cda8..dfd15b2d6bc 100644
--- a/apps/wing/src/cli.ts
+++ b/apps/wing/src/cli.ts
@@ -4,7 +4,6 @@ import { satisfies } from "compare-versions";
 import { optionallyDisplayDisclaimer } from "./analytics/disclaimer";
 import { exportAnalytics } from "./analytics/export";
 import { SNAPSHOTS_HELP } from "./commands/test/snapshots-help";
-import { loadEnvVariables } from "./env";
 import { currentPackage, projectTemplateNames } from "./util";
 
 export const PACKAGE_VERSION = currentPackage.version;
@@ -22,10 +21,6 @@ const DEFAULT_PLATFORM = ["sim"];
 let analyticsExportFile: Promise<string | undefined> | undefined;
 
 function runSubCommand(subCommand: string, path: string = subCommand) {
-  loadEnvVariables({
-    mode: subCommand,
-  });
-
   return async (...args: any[]) => {
     try {
       // paths other than the root path aren't working unless specified in the path arg
diff --git a/apps/wing/src/commands/compile.ts b/apps/wing/src/commands/compile.ts
index 2697a0d0ad8..caefeb6b318 100644
--- a/apps/wing/src/commands/compile.ts
+++ b/apps/wing/src/commands/compile.ts
@@ -1,5 +1,5 @@
 import { promises as fsPromise } from "fs";
-import { relative, resolve } from "path";
+import { dirname, relative, resolve } from "path";
 
 import * as wingCompiler from "@winglang/compiler";
 import { prettyPrintError } from "@winglang/sdk/lib/util/enhanced-error";
@@ -7,6 +7,7 @@ import chalk from "chalk";
 import { CHARS_ASCII, emitDiagnostic, File, Label } from "codespan-wasm";
 import debug from "debug";
 import { glob } from "glob";
+import { loadEnvVariables } from "../env";
 
 // increase the stack trace limit to 50, useful for debugging Rust panics
 // (not setting the limit too high in case of infinite recursion)
@@ -78,7 +79,7 @@ export async function compile(entrypoint?: string, options?: CompileOptions): Pr
     }
     entrypoint = wingFiles[0];
   }
-
+  loadEnvVariables({ cwd: resolve(dirname(entrypoint)) });
   const coloring = chalk.supportsColor ? chalk.supportsColor.hasBasic : false;
   try {
     return await wingCompiler.compile(entrypoint, {
diff --git a/apps/wing/src/commands/pack.ts b/apps/wing/src/commands/pack.ts
index 3929a82e17b..059e00a3543 100644
--- a/apps/wing/src/commands/pack.ts
+++ b/apps/wing/src/commands/pack.ts
@@ -8,6 +8,7 @@ import { BuiltinPlatform } from "@winglang/compiler";
 import packlist from "npm-packlist";
 import * as tar from "tar";
 import { compile } from "./compile";
+import { loadEnvVariables } from "../env";
 
 // TODO: add --dry-run option?
 // TODO: let the user specify library's supported targets in package.json, and compile to each before packaging
@@ -79,6 +80,7 @@ export async function pack(options: PackageOptions = {}): Promise<string> {
   const outfile = options.outFile ? resolve(options.outFile) : undefined;
   const outdir = outfile ? path.dirname(outfile) : userDir;
 
+  loadEnvVariables({ cwd: userDir });
   // check package.json exists
   const originalPkgJsonPath = path.join(userDir, "package.json");
   if (!(await exists(originalPkgJsonPath))) {
diff --git a/apps/wing/src/commands/run.ts b/apps/wing/src/commands/run.ts
index bfd0612f9c4..e93fc5687fe 100644
--- a/apps/wing/src/commands/run.ts
+++ b/apps/wing/src/commands/run.ts
@@ -1,10 +1,11 @@
 import { existsSync } from "fs";
-import { resolve } from "path";
+import { dirname, resolve } from "path";
 import { createConsoleApp } from "@wingconsole/app";
 import { BuiltinPlatform } from "@winglang/compiler";
 import { debug } from "debug";
 import { glob } from "glob";
 import once from "lodash.once";
+import { loadEnvVariables } from "../env";
 import { parseNumericString } from "../util";
 import { beforeShutdown } from "../util.before-shutdown.js";
 
@@ -63,6 +64,8 @@ export async function run(entrypoint?: string, options?: RunOptions) {
     throw new Error(entrypoint + " doesn't exist");
   }
 
+  loadEnvVariables({ cwd: resolve(dirname(entrypoint)) });
+
   if (options?.platform && options?.platform[0] !== BuiltinPlatform.SIM) {
     throw new Error(
       `The first platform in the list must be the sim platform (try "-t sim -t ${options.platform.join(
diff --git a/apps/wing/src/env.ts b/apps/wing/src/env.ts
index 250bd5b5259..f3198d10cc7 100644
--- a/apps/wing/src/env.ts
+++ b/apps/wing/src/env.ts
@@ -11,12 +11,6 @@ export interface EnvLoadOptions {
    * @default process.cwd()
    */
   cwd?: string;
-
-  /**
-   * The mode to load additional environment variables from.
-   * e.g. "wing compile" has mode "compile", which will load ".env.compile" and ".env.compile.local".
-   */
-  mode?: string;
 }
 
 /**
@@ -24,9 +18,7 @@ export interface EnvLoadOptions {
  */
 export function loadEnvVariables(options?: EnvLoadOptions): Record<string, string> | undefined {
   const envDir = options?.cwd ?? process.cwd();
-  const envFiles = DEFAULT_ENV_FILES.concat(
-    options?.mode ? [`.env.${options.mode}`, `.env.${options.mode}.local`] : []
-  ).map((file) => join(envDir, file));
+  const envFiles = DEFAULT_ENV_FILES.map((file) => join(envDir, file));
 
   // Parse `envFiles` and combine their variables into a single object
   const parsed = Object.fromEntries(
diff --git a/libs/wingsdk/src/target-sim/secret.inflight.ts b/libs/wingsdk/src/target-sim/secret.inflight.ts
index c6521dca11e..ebfe657c1bc 100644
--- a/libs/wingsdk/src/target-sim/secret.inflight.ts
+++ b/libs/wingsdk/src/target-sim/secret.inflight.ts
@@ -1,5 +1,3 @@
-import * as fs from "fs";
-import * as path from "path";
 import { SecretAttributes, SecretSchema } from "./schema-resources";
 import { ISecretClient, SECRET_FQN } from "../cloud";
 import {
@@ -11,18 +9,9 @@ import { Json, TraceType } from "../std";
 
 export class Secret implements ISecretClient, ISimulatorResourceInstance {
   private _context: ISimulatorContext | undefined;
-  private readonly secretsFile: string;
   private readonly name: string;
 
   constructor(props: SecretSchema) {
-    this.secretsFile = path.join(process.cwd(), ".env");
-
-    if (!fs.existsSync(this.secretsFile)) {
-      throw new Error(
-        `No secrets file found at ${this.secretsFile} while looking for secret ${props.name}`
-      );
-    }
-
     this.name = props.name;
   }