diff --git a/src/bun.js/node/node_util_binding.zig b/src/bun.js/node/node_util_binding.zig
index bbff581841..89fd03cde0 100644
--- a/src/bun.js/node/node_util_binding.zig
+++ b/src/bun.js/node/node_util_binding.zig
@@ -216,7 +216,7 @@ pub fn parseEnv(globalThis: *jsc.JSGlobalObject, callframe: *jsc.CallFrame) bun.
 
     var map = envloader.Map.init(allocator);
     var p = envloader.Loader.init(&map, allocator);
-    p.loadFromString(str.slice(), true, false);
+    try p.loadFromString(str.slice(), true, false);
 
     var obj = jsc.JSValue.createEmptyObject(globalThis, map.map.count());
     for (map.map.keys(), map.map.values()) |k, v| {
diff --git a/src/cli/create_command.zig b/src/cli/create_command.zig
index 4f7ed16287..e90ec614bd 100644
--- a/src/cli/create_command.zig
+++ b/src/cli/create_command.zig
@@ -213,7 +213,7 @@ pub const CreateCommand = struct {
             break :brk DotEnv.Loader.init(map, ctx.allocator);
         };
 
-        env_loader.loadProcess();
+        try env_loader.loadProcess();
 
         const dirname: string = brk: {
             if (positionals.len == 1) {
@@ -1683,7 +1683,7 @@ pub const CreateCommand = struct {
             break :brk DotEnv.Loader.init(map, ctx.allocator);
         };
 
-        env_loader.loadProcess();
+        try env_loader.loadProcess();
 
         // var unsupported_packages = UnsupportedPackages{};
         const template = brk: {
@@ -2282,7 +2282,7 @@ pub const CreateListExamplesCommand = struct {
             break :brk DotEnv.Loader.init(map, ctx.allocator);
         };
 
-        env_loader.loadProcess();
+        try env_loader.loadProcess();
 
         var progress = Progress{};
         progress.supports_ansi_escape_codes = Output.enable_ansi_colors_stderr;
diff --git a/src/cli/run_command.zig b/src/cli/run_command.zig
index 681e8e286c..800d3a87cb 100644
--- a/src/cli/run_command.zig
+++ b/src/cli/run_command.zig
@@ -786,7 +786,7 @@ pub const RunCommand = struct {
         this_transpiler.resolver.store_fd = false;
 
         if (env == null) {
-            this_transpiler.env.loadProcess();
+            try this_transpiler.env.loadProcess();
 
             if (this_transpiler.env.get("NODE_ENV")) |node_env| {
                 if (strings.eqlComptime(node_env, "production")) {
@@ -973,7 +973,7 @@ pub const RunCommand = struct {
         const root_dir_info = (this_transpiler.resolver.readDirInfo(this_transpiler.fs.top_level_dir) catch null) orelse return shell_out;
 
         {
-            this_transpiler.env.loadProcess();
+            try this_transpiler.env.loadProcess();
 
             if (this_transpiler.env.get("NODE_ENV")) |node_env| {
                 if (strings.eqlComptime(node_env, "production")) {
diff --git a/src/cli/upgrade_command.zig b/src/cli/upgrade_command.zig
index cc83cbc352..08006f4c8c 100644
--- a/src/cli/upgrade_command.zig
+++ b/src/cli/upgrade_command.zig
@@ -358,7 +358,7 @@ pub const UpgradeCommand = struct {
 
             break :brk DotEnv.Loader.init(map, ctx.allocator);
         };
-        env_loader.loadProcess();
+        try env_loader.loadProcess();
 
         const use_canary = brk: {
             const default_use_canary = Environment.is_canary;
diff --git a/src/env_loader.zig b/src/env_loader.zig
index d2399ff509..fb1787f758 100644
--- a/src/env_loader.zig
+++ b/src/env_loader.zig
@@ -393,7 +393,7 @@ pub const Loader = struct {
                         const value: string = entry.value_ptr.value;
 
                         if (strings.startsWith(entry.key_ptr.*, prefix)) {
-                            const key_str = std.fmt.allocPrint(key_allocator, "process.env.{s}", .{entry.key_ptr.*}) catch unreachable;
+                            const key_str = try std.fmt.allocPrint(key_allocator, "process.env.{s}", .{entry.key_ptr.*});
 
                             e_strings[0] = js_ast.E.String{
                                 .data = if (value.len > 0)
@@ -442,7 +442,7 @@ pub const Loader = struct {
                 } else {
                     while (iter.next()) |entry| {
                         const value: string = entry.value_ptr.value;
-                        const key = std.fmt.allocPrint(key_allocator, "process.env.{s}", .{entry.key_ptr.*}) catch unreachable;
+                        const key = try std.fmt.allocPrint(key_allocator, "process.env.{s}", .{entry.key_ptr.*});
 
                         e_strings[0] = js_ast.E.String{
                             .data = if (entry.value_ptr.value.len > 0)
@@ -484,21 +484,21 @@ pub const Loader = struct {
         };
     }
 
-    pub fn loadProcess(this: *Loader) void {
+    pub fn loadProcess(this: *Loader) OOM!void {
         if (this.did_load_process) return;
 
-        this.map.map.ensureTotalCapacity(std.os.environ.len) catch unreachable;
+        try this.map.map.ensureTotalCapacity(std.os.environ.len);
         for (std.os.environ) |_env| {
             var env = bun.span(_env);
             if (strings.indexOfChar(env, '=')) |i| {
                 const key = env[0..i];
                 const value = env[i + 1 ..];
                 if (key.len > 0) {
-                    this.map.put(key, value) catch unreachable;
+                    try this.map.put(key, value);
                 }
             } else {
                 if (env.len > 0) {
-                    this.map.put(env, "") catch unreachable;
+                    try this.map.put(env, "");
                 }
             }
         }
@@ -506,9 +506,11 @@ pub const Loader = struct {
     }
 
     // mostly for tests
-    pub fn loadFromString(this: *Loader, str: string, comptime overwrite: bool, comptime expand: bool) void {
+    pub fn loadFromString(this: *Loader, str: string, comptime overwrite: bool, comptime expand: bool) OOM!void {
         const source = &logger.Source.initPathString("test", str);
-        Parser.parse(source, this.allocator, this.map, overwrite, false, expand);
+        var value_buffer = std.ArrayList(u8).init(this.allocator);
+        defer value_buffer.deinit();
+        try Parser.parse(source, this.allocator, this.map, &value_buffer, overwrite, false, expand);
         std.mem.doNotOptimizeAway(&source);
     }
 
@@ -521,8 +523,13 @@ pub const Loader = struct {
     ) !void {
         const start = std.time.nanoTimestamp();
 
+        // Create a reusable buffer with stack fallback for parsing multiple files
+        var stack_fallback = std.heap.stackFallback(4096, this.allocator);
+        var value_buffer = std.ArrayList(u8).init(stack_fallback.get());
+        defer value_buffer.deinit();
+
         if (env_files.len > 0) {
-            try this.loadExplicitFiles(env_files);
+            try this.loadExplicitFiles(env_files, &value_buffer);
         } else {
             // Do not automatically load .env files in `bun run <script>`
             // Instead, it is the responsibility of the script's instance of `bun` to load .env,
@@ -532,7 +539,7 @@ pub const Loader = struct {
             // See https://github.com/oven-sh/bun/issues/9635#issuecomment-2021350123
             // for more details on how this edge case works.
             if (!skip_default_env)
-                try this.loadDefaultFiles(dir, suffix);
+                try this.loadDefaultFiles(dir, suffix, &value_buffer);
         }
 
         if (!this.quiet) this.printLoaded(start);
@@ -541,6 +548,7 @@ pub const Loader = struct {
     fn loadExplicitFiles(
         this: *Loader,
         env_files: []const []const u8,
+        value_buffer: *std.ArrayList(u8),
     ) !void {
         // iterate backwards, so the latest entry in the latest arg instance assumes the highest priority
         var i: usize = env_files.len;
@@ -550,7 +558,7 @@ pub const Loader = struct {
                 var iter = std.mem.splitBackwardsScalar(u8, arg_value, ',');
                 while (iter.next()) |file_path| {
                     if (file_path.len > 0) {
-                        try this.loadEnvFileDynamic(file_path, false);
+                        try this.loadEnvFileDynamic(file_path, false, value_buffer);
                         analytics.Features.dotenv += 1;
                     }
                 }
@@ -566,25 +574,26 @@ pub const Loader = struct {
         this: *Loader,
         dir: *Fs.FileSystem.DirEntry,
         comptime suffix: DotEnvFileSuffix,
+        value_buffer: *std.ArrayList(u8),
     ) !void {
         const dir_handle: std.fs.Dir = std.fs.cwd();
 
         switch (comptime suffix) {
             .development => {
                 if (dir.hasComptimeQuery(".env.development.local")) {
-                    try this.loadEnvFile(dir_handle, ".env.development.local", false);
+                    try this.loadEnvFile(dir_handle, ".env.development.local", false, value_buffer);
                     analytics.Features.dotenv += 1;
                 }
             },
             .production => {
                 if (dir.hasComptimeQuery(".env.production.local")) {
-                    try this.loadEnvFile(dir_handle, ".env.production.local", false);
+                    try this.loadEnvFile(dir_handle, ".env.production.local", false, value_buffer);
                     analytics.Features.dotenv += 1;
                 }
             },
             .@"test" => {
                 if (dir.hasComptimeQuery(".env.test.local")) {
-                    try this.loadEnvFile(dir_handle, ".env.test.local", false);
+                    try this.loadEnvFile(dir_handle, ".env.test.local", false, value_buffer);
                     analytics.Features.dotenv += 1;
                 }
             },
@@ -592,7 +601,7 @@ pub const Loader = struct {
 
         if (comptime suffix != .@"test") {
             if (dir.hasComptimeQuery(".env.local")) {
-                try this.loadEnvFile(dir_handle, ".env.local", false);
+                try this.loadEnvFile(dir_handle, ".env.local", false, value_buffer);
                 analytics.Features.dotenv += 1;
             }
         }
@@ -600,26 +609,26 @@ pub const Loader = struct {
         switch (comptime suffix) {
             .development => {
                 if (dir.hasComptimeQuery(".env.development")) {
-                    try this.loadEnvFile(dir_handle, ".env.development", false);
+                    try this.loadEnvFile(dir_handle, ".env.development", false, value_buffer);
                     analytics.Features.dotenv += 1;
                 }
             },
             .production => {
                 if (dir.hasComptimeQuery(".env.production")) {
-                    try this.loadEnvFile(dir_handle, ".env.production", false);
+                    try this.loadEnvFile(dir_handle, ".env.production", false, value_buffer);
                     analytics.Features.dotenv += 1;
                 }
             },
             .@"test" => {
                 if (dir.hasComptimeQuery(".env.test")) {
-                    try this.loadEnvFile(dir_handle, ".env.test", false);
+                    try this.loadEnvFile(dir_handle, ".env.test", false, value_buffer);
                     analytics.Features.dotenv += 1;
                 }
             },
         }
 
         if (dir.hasComptimeQuery(".env")) {
-            try this.loadEnvFile(dir_handle, ".env", false);
+            try this.loadEnvFile(dir_handle, ".env", false, value_buffer);
             analytics.Features.dotenv += 1;
         }
     }
@@ -694,6 +703,7 @@ pub const Loader = struct {
         dir: std.fs.Dir,
         comptime base: string,
         comptime override: bool,
+        value_buffer: *std.ArrayList(u8),
     ) !void {
         if (@field(this, base) != null) {
             return;
@@ -765,10 +775,11 @@ pub const Loader = struct {
 
         const source = &logger.Source.initPathString(base, buf[0..amount_read]);
 
-        Parser.parse(
+        try Parser.parse(
             source,
             this.allocator,
             this.map,
+            value_buffer,
             override,
             false,
             true,
@@ -781,6 +792,7 @@ pub const Loader = struct {
         this: *Loader,
         file_path: []const u8,
         comptime override: bool,
+        value_buffer: *std.ArrayList(u8),
     ) !void {
         if (this.custom_files_loaded.contains(file_path)) {
             return;
@@ -836,10 +848,11 @@ pub const Loader = struct {
 
         const source = &logger.Source.initPathString(file_path, buf[0..amount_read]);
 
-        Parser.parse(
+        try Parser.parse(
             source,
             this.allocator,
             this.map,
+            value_buffer,
             override,
             false,
             true,
@@ -852,10 +865,9 @@ pub const Loader = struct {
 const Parser = struct {
     pos: usize = 0,
     src: string,
+    value_buffer: *std.ArrayList(u8),
 
     const whitespace_chars = "\t\x0B\x0C \xA0\n\r";
-    // You get 4k. I hope you don't need more than that.
-    threadlocal var value_buffer: [4096]u8 = undefined;
 
     fn skipLine(this: *Parser) void {
         if (strings.indexOfAny(this.src[this.pos..], "\n\r")) |i| {
@@ -912,10 +924,10 @@ const Parser = struct {
         return null;
     }
 
-    fn parseQuoted(this: *Parser, comptime quote: u8) ?string {
+    fn parseQuoted(this: *Parser, comptime quote: u8) !?string {
         if (comptime Environment.allow_assert) bun.assert(this.src[this.pos] == quote);
         const start = this.pos;
-        const max_len = value_buffer.len;
+        this.value_buffer.clearRetainingCapacity(); // Reset the buffer
         var end = start + 1;
         while (end < this.src.len) : (end += 1) {
             switch (this.src[end]) {
@@ -929,52 +941,42 @@ const Parser = struct {
                         strings.indexOfChar(this.src[end..this.pos], '\n') != null or
                         strings.indexOfChar(this.src[end..this.pos], '\r') != null)
                     {
-                        var ptr: usize = 0;
                         var i = start;
-                        while (i < end and ptr < max_len) {
+                        while (i < end) {
                             switch (this.src[i]) {
                                 '\\' => if (comptime quote == '"') {
                                     if (comptime Environment.allow_assert) bun.assert(i + 1 < end);
                                     switch (this.src[i + 1]) {
                                         'n' => {
-                                            value_buffer[ptr] = '\n';
-                                            ptr += 1;
+                                            try this.value_buffer.append('\n');
                                             i += 2;
                                         },
                                         'r' => {
-                                            value_buffer[ptr] = '\r';
-                                            ptr += 1;
+                                            try this.value_buffer.append('\r');
                                             i += 2;
                                         },
                                         else => {
-                                            if (ptr + 1 < max_len) {
-                                                value_buffer[ptr] = this.src[i];
-                                                value_buffer[ptr + 1] = this.src[i + 1];
-                                            }
-                                            ptr += 2;
+                                            try this.value_buffer.appendSlice(this.src[i..][0..2]);
                                             i += 2;
                                         },
                                     }
                                 } else {
-                                    value_buffer[ptr] = '\\';
-                                    ptr += 1;
+                                    try this.value_buffer.append('\\');
                                     i += 1;
                                 },
                                 '\r' => {
                                     i += 1;
                                     if (i >= end or this.src[i] != '\n') {
-                                        value_buffer[ptr] = '\n';
-                                        ptr += 1;
+                                        try this.value_buffer.append('\n');
                                     }
                                 },
                                 else => |c| {
-                                    value_buffer[ptr] = c;
-                                    ptr += 1;
+                                    try this.value_buffer.append(c);
                                     i += 1;
                                 },
                             }
                         }
-                        return value_buffer[0..ptr];
+                        return this.value_buffer.items;
                     }
                     this.pos = start;
                 },
@@ -984,14 +986,14 @@ const Parser = struct {
         return null;
     }
 
-    fn parseValue(this: *Parser, comptime is_process: bool) string {
+    fn parseValue(this: *Parser, comptime is_process: bool) OOM!string {
         const start = this.pos;
         this.skipWhitespaces();
         var end = this.pos;
         if (end >= this.src.len) return this.src[this.src.len..];
         switch (this.src[end]) {
             inline '`', '"', '\'' => |quote| {
-                if (this.parseQuoted(quote)) |value| {
+                if (try this.parseQuoted(quote)) |value| {
                     return if (comptime is_process) value else value[1 .. value.len - 1];
                 }
             },
@@ -1008,22 +1010,17 @@ const Parser = struct {
         return strings.trim(this.src[start..end], whitespace_chars);
     }
 
-    inline fn writeBackwards(ptr: usize, bytes: []const u8) usize {
-        const end = ptr;
-        const start = end - bytes.len;
-        bun.copy(u8, value_buffer[start..end], bytes);
-        return start;
-    }
-
-    fn expandValue(map: *Map, value: string) ?string {
+    fn expandValue(this: *Parser, map: *Map, value: string) OOM!?string {
         if (value.len < 2) return null;
-        var ptr = value_buffer.len;
+
+        this.value_buffer.clearRetainingCapacity();
+
         var pos = value.len - 2;
         var last = value.len;
         while (true) : (pos -= 1) {
             if (value[pos] == '$') {
                 if (pos > 0 and value[pos - 1] == '\\') {
-                    ptr = writeBackwards(ptr, value[pos..last]);
+                    try this.value_buffer.insertSlice(0, value[pos..last]);
                     pos -= 1;
                 } else {
                     var end = if (value[pos + 1] == '{') pos + 2 else pos + 1;
@@ -1047,8 +1044,8 @@ const Parser = struct {
                         break :brk value[value_start..end];
                     } else "";
                     if (end < value.len and value[end] == '}') end += 1;
-                    ptr = writeBackwards(ptr, value[end..last]);
-                    ptr = writeBackwards(ptr, lookup_value orelse default_value);
+                    try this.value_buffer.insertSlice(0, value[end..last]);
+                    try this.value_buffer.insertSlice(0, lookup_value orelse default_value);
                 }
                 last = pos;
             }
@@ -1057,8 +1054,10 @@ const Parser = struct {
                 break;
             }
         }
-        if (last > 0) ptr = writeBackwards(ptr, value[0..last]);
-        return value_buffer[ptr..];
+        if (last > 0) {
+            try this.value_buffer.insertSlice(0, value[0..last]);
+        }
+        return this.value_buffer.items;
     }
 
     fn _parse(
@@ -1068,15 +1067,15 @@ const Parser = struct {
         comptime override: bool,
         comptime is_process: bool,
         comptime expand: bool,
-    ) void {
+    ) OOM!void {
         var count = map.map.count();
         while (this.pos < this.src.len) {
             const key = this.parseKey(true) orelse {
                 this.skipLine();
                 continue;
             };
-            const value = this.parseValue(is_process);
-            const entry = map.map.getOrPut(key) catch unreachable;
+            const value = try this.parseValue(is_process);
+            const entry = try map.map.getOrPut(key);
             if (entry.found_existing) {
                 if (entry.index < count) {
                     // Allow keys defined later in the same file to override keys defined earlier
@@ -1087,7 +1086,7 @@ const Parser = struct {
                 }
             }
             entry.value_ptr.* = .{
-                .value = allocator.dupe(u8, value) catch unreachable,
+                .value = try allocator.dupe(u8, value),
                 .conditional = false,
             };
         }
@@ -1096,10 +1095,10 @@ const Parser = struct {
             while (it.next()) |entry| {
                 if (count > 0) {
                     count -= 1;
-                } else if (expandValue(map, entry.value_ptr.value)) |value| {
+                } else if (try this.expandValue(map, entry.value_ptr.value)) |value| {
                     allocator.free(entry.value_ptr.value);
                     entry.value_ptr.* = .{
-                        .value = allocator.dupe(u8, value) catch unreachable,
+                        .value = try allocator.dupe(u8, value),
                         .conditional = false,
                     };
                 }
@@ -1111,12 +1110,18 @@ const Parser = struct {
         source: *const logger.Source,
         allocator: std.mem.Allocator,
         map: *Map,
+        value_buffer: *std.ArrayList(u8),
         comptime override: bool,
         comptime is_process: bool,
         comptime expand: bool,
-    ) void {
-        var parser = Parser{ .src = source.contents };
-        parser._parse(allocator, map, override, is_process, expand);
+    ) OOM!void {
+        // Clear the buffer before each parse to ensure no leftover data
+        value_buffer.clearRetainingCapacity();
+        var parser = Parser{
+            .src = source.contents,
+            .value_buffer = value_buffer,
+        };
+        try parser._parse(allocator, map, override, is_process, expand);
     }
 };
 
@@ -1135,7 +1140,7 @@ pub const Map = struct {
 
     map: HashTable,
 
-    pub fn createNullDelimitedEnvMap(this: *Map, arena: std.mem.Allocator) ![:null]?[*:0]const u8 {
+    pub fn createNullDelimitedEnvMap(this: *Map, arena: std.mem.Allocator) OOM![:null]?[*:0]const u8 {
         var env_map = &this.map;
 
         const envp_count = env_map.count();
@@ -1159,7 +1164,7 @@ pub const Map = struct {
     /// the keys and values, but instead points into the memory of the bun env map.
     ///
     /// To prevent
-    pub fn stdEnvMap(this: *Map, allocator: std.mem.Allocator) !StdEnvMapWrapper {
+    pub fn stdEnvMap(this: *Map, allocator: std.mem.Allocator) OOM!StdEnvMapWrapper {
         var env_map = std.process.EnvMap.init(allocator);
 
         var iter = this.map.iterator();
@@ -1217,7 +1222,7 @@ pub const Map = struct {
         return Map{ .map = HashTable.init(allocator) };
     }
 
-    pub inline fn put(this: *Map, key: string, value: string) !void {
+    pub inline fn put(this: *Map, key: string, value: string) OOM!void {
         if (Environment.isWindows and Environment.allow_assert) {
             bun.assert(bun.strings.indexOfChar(key, '\x00') == null);
         }
@@ -1227,7 +1232,7 @@ pub const Map = struct {
         });
     }
 
-    pub fn ensureUnusedCapacity(this: *Map, additional_count: usize) !void {
+    pub fn ensureUnusedCapacity(this: *Map, additional_count: usize) OOM!void {
         return this.map.ensureUnusedCapacity(additional_count);
     }
 
@@ -1241,7 +1246,7 @@ pub const Map = struct {
         });
     }
 
-    pub inline fn putAllocKeyAndValue(this: *Map, allocator: std.mem.Allocator, key: string, value: string) !void {
+    pub inline fn putAllocKeyAndValue(this: *Map, allocator: std.mem.Allocator, key: string, value: string) OOM!void {
         const gop = try this.map.getOrPut(key);
         gop.value_ptr.* = .{
             .value = try allocator.dupe(u8, value),
@@ -1252,7 +1257,7 @@ pub const Map = struct {
         }
     }
 
-    pub inline fn putAllocKey(this: *Map, allocator: std.mem.Allocator, key: string, value: string) !void {
+    pub inline fn putAllocKey(this: *Map, allocator: std.mem.Allocator, key: string, value: string) OOM!void {
         const gop = try this.map.getOrPut(key);
         gop.value_ptr.* = .{
             .value = value,
@@ -1263,14 +1268,14 @@ pub const Map = struct {
         }
     }
 
-    pub inline fn putAllocValue(this: *Map, allocator: std.mem.Allocator, key: string, value: string) !void {
+    pub inline fn putAllocValue(this: *Map, allocator: std.mem.Allocator, key: string, value: string) OOM!void {
         try this.map.put(key, .{
             .value = try allocator.dupe(u8, value),
             .conditional = false,
         });
     }
 
-    pub inline fn getOrPutWithoutValue(this: *Map, key: string) !GetOrPutResult {
+    pub inline fn getOrPutWithoutValue(this: *Map, key: string) OOM!GetOrPutResult {
         return this.map.getOrPut(key);
     }
 
@@ -1281,11 +1286,11 @@ pub const Map = struct {
         while (iter.next()) |entry| {
             _ = try writer.write("\n    ");
 
-            writer.write(entry.key_ptr.*) catch unreachable;
+            try writer.write(entry.key_ptr.*);
 
             _ = try writer.write(": ");
 
-            writer.write(entry.value_ptr.*) catch unreachable;
+            try writer.write(entry.value_ptr.*);
 
             if (iter.index <= self.map.count() - 1) {
                 _ = try writer.write(", ");
@@ -1302,14 +1307,14 @@ pub const Map = struct {
         return if (this.map.get(key)) |entry| entry.value else null;
     }
 
-    pub inline fn putDefault(this: *Map, key: string, value: string) !void {
+    pub inline fn putDefault(this: *Map, key: string, value: string) OOM!void {
         _ = try this.map.getOrPutValue(key, .{
             .value = value,
             .conditional = false,
         });
     }
 
-    pub inline fn getOrPut(this: *Map, key: string, value: string) !void {
+    pub inline fn getOrPut(this: *Map, key: string, value: string) OOM!void {
         _ = try this.map.getOrPutValue(key, .{
             .value = value,
             .conditional = false,
@@ -1320,7 +1325,7 @@ pub const Map = struct {
         _ = this.map.swapRemove(key);
     }
 
-    pub fn cloneWithAllocator(this: *const Map, new_allocator: std.mem.Allocator) !Map {
+    pub fn cloneWithAllocator(this: *const Map, new_allocator: std.mem.Allocator) OOM!Map {
         return .{ .map = try this.map.cloneWithAllocator(new_allocator) };
     }
 };
@@ -1338,6 +1343,7 @@ const which = @import("./which.zig").which;
 
 const bun = @import("bun");
 const Environment = bun.Environment;
+const OOM = bun.OOM;
 const Output = bun.Output;
 const analytics = bun.analytics;
 const logger = bun.logger;
diff --git a/src/install/PackageManager.zig b/src/install/PackageManager.zig
index 55e4d3fe77..fcb33f68ed 100644
--- a/src/install/PackageManager.zig
+++ b/src/install/PackageManager.zig
@@ -783,7 +783,7 @@ pub fn init(
         break :brk loader;
     };
 
-    env.loadProcess();
+    try env.loadProcess();
     try env.load(entries_option.entries, &[_][]u8{}, .production, false);
 
     initializeStore();
diff --git a/src/install/lockfile.zig b/src/install/lockfile.zig
index 28510beeaa..a0dbc5e6f6 100644
--- a/src/install/lockfile.zig
+++ b/src/install/lockfile.zig
@@ -1039,7 +1039,7 @@ pub const Printer = struct {
             break :brk loader;
         };
 
-        env_loader.loadProcess();
+        try env_loader.loadProcess();
         try env_loader.load(entries_option.entries, &[_][]u8{}, .production, false);
         var log = logger.Log.init(allocator);
         try options.load(
diff --git a/src/transpiler.zig b/src/transpiler.zig
index 3ec22ee790..44563c5ccd 100644
--- a/src/transpiler.zig
+++ b/src/transpiler.zig
@@ -480,7 +480,7 @@ pub const Transpiler = struct {
 
                 // Process always has highest priority.
                 const was_production = this.options.production;
-                this.env.loadProcess();
+                try this.env.loadProcess();
                 const has_production_env = this.env.isProduction();
                 if (!was_production and has_production_env) {
                     this.options.setProduction(true);
@@ -496,7 +496,7 @@ pub const Transpiler = struct {
                 }
             },
             .disable => {
-                this.env.loadProcess();
+                try this.env.loadProcess();
                 if (this.env.isProduction()) {
                     this.options.setProduction(true);
                     this.resolver.opts.setProduction(true);
diff --git a/test/cli/run/env.test.ts b/test/cli/run/env.test.ts
index 2bf13d3a9f..295c0e0056 100644
--- a/test/cli/run/env.test.ts
+++ b/test/cli/run/env.test.ts
@@ -443,21 +443,19 @@ describe("boundary tests", () => {
 
   test("buffer boundary", () => {
     const expected = "a".repeat(4094);
-    let content = expected + "a";
     const dir = tempDirWithFiles("dotenv", {
-      ".env": `KEY="${content}"`,
+      ".env": `KEY="${expected + "a"}"`,
       "index.ts": "console.log(process.env.KEY);",
     });
     const { stdout } = bunRun(`${dir}/index.ts`);
 
-    content = expected + "\\n";
     const dir2 = tempDirWithFiles("dotenv", {
-      ".env": `KEY="${content}"`,
+      ".env": `KEY="${expected + "\\n"}"`,
       "index.ts": "console.log(process.env.KEY);",
     });
     const { stdout: stdout2 } = bunRun(`${dir2}/index.ts`);
     // should be truncated
-    expect(stdout).toBe(expected);
+    expect(stdout).toBe(expected + "a");
     expect(stdout2).toBe(expected);
   });
 });
@@ -821,3 +819,41 @@ test("NODE_ENV=test loads .env.test even when .env.production exists", () => {
   const { stdout } = bunRun(`${dir}/index.ts`, { NODE_ENV: "test" });
   expect(stdout).toBe("test");
 });
+
+describe("env loader buffer handling", () => {
+  test("handles large quoted values with escape sequences", () => {
+    // This test ensures the env loader properly handles large values that exceed the initial buffer size
+    // The env loader doesn't process escape sequences, so \\\\ remains as \\\\
+    const dir = tempDirWithFiles("dotenv-buffer-overflow", {
+      ".env": `OVERFLOW_VAR="${"\\\\".repeat(2049)}"`, // 2049 * 2 = 4098 characters
+      "index.ts": "console.log(process.env.OVERFLOW_VAR?.length || 0);",
+    });
+    const { stdout } = bunRun(`${dir}/index.ts`);
+    expect(stdout).toBe("4098"); // Each \\\\ is 2 characters
+  });
+
+  test("handles multiple large values in same file", () => {
+    const dir = tempDirWithFiles("dotenv-multiple-large", {
+      ".env": `
+LARGE1="${"a".repeat(3000)}"
+LARGE2="${"b".repeat(3000)}"
+LARGE3="${"c".repeat(3000)}"
+`,
+      "index.ts":
+        "console.log([process.env.LARGE1?.length, process.env.LARGE2?.length, process.env.LARGE3?.length].join(','));",
+    });
+    const { stdout } = bunRun(`${dir}/index.ts`);
+    expect(stdout).toBe("3000,3000,3000");
+  });
+
+  test("handles escape sequences at buffer boundaries", () => {
+    // Test that values with content near the old 4096-byte buffer boundary work correctly
+    const prefix = "x".repeat(4090);
+    const dir = tempDirWithFiles("dotenv-boundary-escape", {
+      ".env": `BOUNDARY="${prefix}suffix"`, // Total length would exceed 4096
+      "index.ts": "console.log(process.env.BOUNDARY?.length || 0);",
+    });
+    const { stdout } = bunRun(`${dir}/index.ts`);
+    expect(stdout).toBe("4096");
+  });
+});