diff --git a/src/install/PackageManager/install_with_manager.zig b/src/install/PackageManager/install_with_manager.zig
index 156d817f60..2dd6767a27 100644
--- a/src/install/PackageManager/install_with_manager.zig
+++ b/src/install/PackageManager/install_with_manager.zig
@@ -364,12 +364,14 @@ pub fn installWithManager(
                         for (manager.lockfile.buffers.dependencies.items, 0..) |*dependency, dependency_i| {
                             if (std.mem.indexOfScalar(PackageNameHash, all_name_hashes, dependency.name_hash)) |_| {
                                 manager.lockfile.buffers.resolutions.items[dependency_i] = invalid_package_id;
-                                try manager.enqueueDependencyWithMain(
+                                manager.enqueueDependencyWithMain(
                                     @truncate(dependency_i),
                                     dependency,
                                     invalid_package_id,
                                     false,
-                                );
+                                ) catch |err| {
+                                    addDependencyError(manager, dependency, err);
+                                };
                             }
                         }
                     }
@@ -380,12 +382,14 @@ pub fn installWithManager(
                             if (dep.version.tag != .catalog) continue;
 
                             manager.lockfile.buffers.resolutions.items[dep_id] = invalid_package_id;
-                            try manager.enqueueDependencyWithMain(
+                            manager.enqueueDependencyWithMain(
                                 dep_id,
                                 dep,
                                 invalid_package_id,
                                 false,
-                            );
+                            ) catch |err| {
+                                addDependencyError(manager, dep, err);
+                            };
                         }
                     }
 
@@ -401,12 +405,14 @@ pub fn installWithManager(
                             if (mapping[counter_i] == invalid_package_id) {
                                 const dependency_i = counter_i + off;
                                 const dependency = manager.lockfile.buffers.dependencies.items[dependency_i];
-                                try manager.enqueueDependencyWithMain(
+                                manager.enqueueDependencyWithMain(
                                     dependency_i,
                                     &dependency,
                                     manager.lockfile.buffers.resolutions.items[dependency_i],
                                     false,
-                                );
+                                ) catch |err| {
+                                    addDependencyError(manager, &dependency, err);
+                                };
                             }
                         }
                     }
@@ -1101,6 +1107,28 @@ pub fn getWorkspaceFilters(manager: *PackageManager, original_cwd: []const u8) !
     return .{ workspace_filters.items, install_root_dependencies };
 }
 
+/// Adds a contextual error for a dependency resolution failure.
+/// This provides better error messages than just propagating the raw error.
+/// The error is logged to manager.log, and the install will fail later when
+/// manager.log.hasErrors() is checked.
+fn addDependencyError(manager: *PackageManager, dependency: *const Dependency, err: anyerror) void {
+    const lockfile = manager.lockfile;
+    const note = .{
+        .fmt = "error occurred while resolving {f}",
+        .args = .{bun.fmt.fmtPath(u8, lockfile.str(&dependency.realname()), .{
+            .path_sep = switch (dependency.version.tag) {
+                .folder => .auto,
+                else => .any,
+            },
+        })},
+    };
+
+    if (dependency.behavior.isOptional() or dependency.behavior.isPeer())
+        manager.log.addWarningWithNote(null, .{}, manager.allocator, @errorName(err), note.fmt, note.args) catch unreachable
+    else
+        manager.log.addZigErrorWithNote(manager.allocator, err, note.fmt, note.args) catch unreachable;
+}
+
 const security_scanner = @import("./security_scanner.zig");
 const std = @import("std");
 const installHoistedPackages = @import("../hoisted_install.zig").installHoistedPackages;
diff --git a/test/regression/issue/26337.test.ts b/test/regression/issue/26337.test.ts
new file mode 100644
index 0000000000..8c6f27749d
--- /dev/null
+++ b/test/regression/issue/26337.test.ts
@@ -0,0 +1,78 @@
+// https://github.com/oven-sh/bun/issues/26337
+// Test that `bun install` with a stale lockfile that has a `file:` dependency path
+// that differs from the package.json shows a helpful error message indicating which
+// dependency caused the issue, rather than the misleading "Bun could not find a
+// package.json file to install from" error.
+
+import { describe, expect, it } from "bun:test";
+import { bunEnv, bunExe, tempDir } from "harness";
+
+describe("issue #26337 - missing file: dependency error should show dependency name", () => {
+  it("should show which dependency path is missing when lockfile has stale file: path", async () => {
+    // Create a workspace with a valid file: dependency
+    using dir = tempDir("issue-26337", {
+      "package.json": JSON.stringify({
+        name: "repro",
+        dependencies: {
+          "@scope/dep": "file:./packages/@scope/dep",
+        },
+      }),
+      "packages/@scope/dep/package.json": JSON.stringify({
+        name: "@scope/dep",
+        version: "1.0.0",
+      }),
+    });
+
+    // First install to create a lockfile with the valid path
+    await using installProc = Bun.spawn({
+      cmd: [bunExe(), "install"],
+      cwd: String(dir),
+      env: bunEnv,
+      stdout: "pipe",
+      stderr: "pipe",
+    });
+
+    // Consume streams to prevent buffer filling
+    const [, , installExitCode] = await Promise.all([
+      installProc.stdout.text(),
+      installProc.stderr.text(),
+      installProc.exited,
+    ]);
+    expect(installExitCode).toBe(0);
+
+    // Now update the package.json to point to a non-existent path
+    // This creates the stale lockfile scenario
+    await Bun.write(
+      `${dir}/package.json`,
+      JSON.stringify({
+        name: "repro",
+        dependencies: {
+          "@scope/dep": "file:./nonexistent/path",
+        },
+      }),
+    );
+
+    // Run bun install again - this should show a helpful error
+    await using failProc = Bun.spawn({
+      cmd: [bunExe(), "install"],
+      cwd: String(dir),
+      env: bunEnv,
+      stdout: "pipe",
+      stderr: "pipe",
+    });
+
+    const [stdout, stderr, exitCode] = await Promise.all([
+      failProc.stdout.text(),
+      failProc.stderr.text(),
+      failProc.exited,
+    ]);
+
+    // The error output should mention the dependency name
+    const output = stdout + stderr;
+    expect(output).toContain("@scope/dep");
+    expect(output).toContain("error occurred while resolving");
+
+    // The install should fail
+    expect(exitCode).toBe(1);
+  });
+});