diff --git a/src/features/run/configs.test.ts b/src/features/run/configs.test.ts
index d27eb265..1a02731b 100644
--- a/src/features/run/configs.test.ts
+++ b/src/features/run/configs.test.ts
@@ -256,6 +256,37 @@ describe("context configuration", () => {
     expect(contextConfig("docs/readme.md", configs)).toBeNull();
   });
 
+  it("runs a module that imports relatively as a module of its package", () => {
+    const cli = "from .models import Priority, TaskList\n\n\ndef main():\n    pass\n";
+    expect(contextConfig("src/tasks/cli.py", configs, cli)).toMatchObject({
+      kind: "python",
+      command: "../.venv/bin/python",
+      args: ["-m", "tasks.cli"],
+      cwd: "src",
+      debugAdapter: "debugpy",
+    });
+    expect(contextConfig("app/api/routes.py", [], "from . import models\n")).toMatchObject({
+      command: "python3",
+      args: ["-m", "app.api.routes"],
+      cwd: null,
+    });
+    expect(contextConfig("src/app/__main__.py", [], "from .cli import main\n")).toMatchObject({
+      args: ["-m", "app"],
+      cwd: "src",
+    });
+    // Inside a nested Python project: from its folder (the venv command stays relative to the root).
+    const nested = [cfg({ id: "pytest", kind: "pytest", command: "backend/.venv/bin/pytest", cwd: "backend" })];
+    expect(contextConfig("backend/app/jobs.py", nested, "from .db import session\n")).toMatchObject({
+      command: "../backend/.venv/bin/python",
+      args: ["-m", "app.jobs"],
+      cwd: "backend",
+    });
+    // Absolute imports, a top-level file, a folder that can't be a package: as a script.
+    expect(contextConfig("src/tasks/cli.py", configs, "import os\n")!.args).toEqual(["src/tasks/cli.py"]);
+    expect(contextConfig("tool.py", [], "from .x import y\n")!.args).toEqual(["tool.py"]);
+    expect(contextConfig("my-scripts/run.py", [], "from .x import y\n")!.args).toEqual(["my-scripts/run.py"]);
+  });
+
   it("runs pytest for a test file even without a detected pytest config", () => {
     expect(contextConfig("worker/test_worker.py", [])).toMatchObject({
       command: "python3",
diff --git a/src/features/run/context.ts b/src/features/run/context.ts
index 69e2050e..fe8c40b9 100644
--- a/src/features/run/context.ts
+++ b/src/features/run/context.ts
@@ -236,7 +236,48 @@ function mainConfigFor(relPath: string, configs: RunConfig[]): RunConfig | null
   return null;
 }
 
-function scriptConfigFor(relPath: string, configs: RunConfig[], windows = isWindows()): RunConfig | null {
+/** `from .models import …`, `from . import x`: the file is a module of a package. */
+const RELATIVE_IMPORT = /^[ \t]*from[ \t]+\.+[\w.]*[ \t]+import\b/m;
+const IDENTIFIER = /^[A-Za-z_]\w*$/;
+
+/**
+ * A module that imports relatively runs as `python -m <package>.<module>` from the folder its top
+ * package sits in (the last `src` of its path, else the Python project's folder): run as a script,
+ * its relative imports fail. `null` for other files.
+ */
+export function pythonModuleRun(
+  relPath: string,
+  content: string | undefined,
+  configs: RunConfig[],
+): { cwd: string; module: string } | null {
+  if (!content || !RELATIVE_IMPORT.test(content)) return null;
+  const project = closest(
+    configs.filter((c) => c.kind === "python" || c.kind === "pytest"),
+    relPath,
+  )?.cwd?.replace(/^\.\/?|\/+$/g, "");
+  const segs = relPath.replace(/\.py$/, "").split("/");
+  const first = project && relPath.startsWith(`${project}/`) ? project.split("/").length : 0;
+  const src = segs.lastIndexOf("src", segs.length - 2);
+  const start = src >= first ? src + 1 : first;
+  const parts = segs.slice(start);
+  // Only a module inside a package can import relatively.
+  if (parts.length < 2 || !parts.every((p) => IDENTIFIER.test(p))) return null;
+  if (parts.at(-1) === "__main__" || parts.at(-1) === "__init__") parts.pop();
+  return { cwd: segs.slice(0, start).join("/"), module: parts.join(".") };
+}
+
+/** A command relative to the project root (`.venv/bin/python`), from `cwd` inside it. */
+function fromSubfolder(command: string, cwd: string): string {
+  if (!cwd || !command.includes("/") || command.startsWith("/") || /^[A-Za-z]:/.test(command)) return command;
+  return "../".repeat(cwd.split("/").length) + command;
+}
+
+function scriptConfigFor(
+  relPath: string,
+  configs: RunConfig[],
+  windows = isWindows(),
+  content?: string,
+): RunConfig | null {
   const base: RunConfig = {
     id: `context:file:${relPath}`,
     name: relPath.split("/").pop() ?? relPath,
@@ -251,10 +292,18 @@ function scriptConfigFor(relPath: string, configs: RunConfig[], windows = isWind
   };
   if (relPath.endsWith(".py")) {
     // Reuse the project's interpreter (venv / uv / poetry) when detected.
-    const py = projectPython(configs);
-    if (py)
-      return { ...base, kind: "python", command: py.command, args: [...py.prefix, relPath], debugAdapter: "debugpy" };
-    return { ...base, kind: "python", command: "python3", args: [relPath], debugAdapter: "debugpy" };
+    const py = projectPython(configs) ?? { command: "python3", prefix: [] };
+    const module = pythonModuleRun(relPath, content, configs);
+    if (module)
+      return {
+        ...base,
+        kind: "python",
+        command: fromSubfolder(py.command, module.cwd),
+        args: [...py.prefix, "-m", module.module],
+        cwd: module.cwd || null,
+        debugAdapter: "debugpy",
+      };
+    return { ...base, kind: "python", command: py.command, args: [...py.prefix, relPath], debugAdapter: "debugpy" };
   }
   if (/\.[cm]?js$/.test(relPath)) return { ...base, command: "node", args: [relPath], debugAdapter: "js-debug" };
   if (/\.ts$/.test(relPath)) return { ...base, command: "npx", args: ["tsx", relPath], debugAdapter: "js-debug" };
@@ -278,7 +327,7 @@ export function contextConfig(
 ): RunConfig | null {
   const role = fileRole(relPath, content, windows, hasDjangoTests(configs));
   if (role === "test") return testConfigFor(relPath, configs);
-  if (role === "main") return mainConfigFor(relPath, configs) ?? scriptConfigFor(relPath, configs, windows);
-  if (role === "script") return scriptConfigFor(relPath, configs, windows);
+  if (role === "main") return mainConfigFor(relPath, configs) ?? scriptConfigFor(relPath, configs, windows, content);
+  if (role === "script") return scriptConfigFor(relPath, configs, windows, content);
   return null;
 }