diff --git a/src/features/run/contextRun.ts b/src/features/run/contextRun.ts
index be9e39187..c67144c11 100644
--- a/src/features/run/contextRun.ts
+++ b/src/features/run/contextRun.ts
@@ -29,9 +29,11 @@ import {
   scriptLanguage,
   type ContextInput,
   type Produced,
+  hasRelativeImports,
 } from "./producers";
 import { runWithExecutor } from "./executors";
 import { goModulePath, loadGoModules } from "./goModules";
+import { isPythonPackage, loadPythonPackages } from "./pythonPackages";
 import { remoteDebugBlocked } from "./remote";
 import { toolEnv } from "./runtimes";
 import { adoptTemporary, loadConfigs, modifyTemporary, startRun, useRun } from "./store";
@@ -88,7 +90,8 @@ export async function produceResolved(input: ContextInput, dir = false): Promise
   const configs = useRun.getState().configs;
   if (dir || /\.go$/.test(input.path)) await loadGoModules(input.root, configs);
   if (dir) return produceDirectory({ ...input, goModule: goModulePath });
-  const fresh = { ...input, configs, goModule: goModulePath };
+  if (/\.py$/.test(input.path) && hasRelativeImports(input.content)) await loadPythonPackages(input.path);
+  const fresh = { ...input, configs, goModule: goModulePath, pythonPackage: isPythonPackage };
   const named = produceContext(fresh, OPTIMISTIC);
   if (!named) return null;
   // Project configurations (tests, cargo, gradle…) need no runtime lookup.
diff --git a/src/features/run/index.ts b/src/features/run/index.ts
index e32a1eec6..a663c368c 100644
--- a/src/features/run/index.ts
+++ b/src/features/run/index.ts
@@ -38,6 +38,7 @@ import { EditConfigsOverlay } from "./EditConfigsDialog";
 import { openImport } from "./importConfigs";
 import { registerGoActions } from "./goActions";
 import { invalidateGoModules } from "./goModules";
+import { invalidatePythonPackages } from "./pythonPackages";
 import { RunWidget } from "./RunWidget";
 import { runConfigsRunAnything } from "./runAnything";
 import { cleanupRemovedProject, recordRun, runServiceProvider } from "./services";
@@ -574,6 +575,7 @@ export function activate(): () => void {
     onIdeEvent("fsChanged", (e) => {
       const paths = [...e.created, ...e.modified, ...e.removed];
       if (paths.some((p) => /(?:^|\/)go\.(?:mod|work)$/.test(p))) invalidateGoModules();
+      if (paths.some((p) => p.endsWith("/__init__.py"))) invalidatePythonPackages();
       if (paths.some((p) => CONFIG_FILES.test(p))) scheduleReload();
     }),
     onIdeEvent("runExited", (e) => {
diff --git a/src/features/run/producers.test.ts b/src/features/run/producers.test.ts
index 00299b4ce..6a800050c 100644
--- a/src/features/run/producers.test.ts
+++ b/src/features/run/producers.test.ts
@@ -162,6 +162,31 @@ describe("single-file producers (scratches)", () => {
     expect(produceContext(scratch("hi.py"), env({}))!.missing!.title).toBe("Cannot run 'hi.py'");
   });
 
+  it("Python: a module with relative imports runs with -m from above its top package", () => {
+    const venv = [cfg({ id: "pytest", kind: "pytest", command: ".venv/bin/pytest" })];
+    const packages = new Set([`${ROOT}/src/tasks`, `${ROOT}/src/tasks/sub`]);
+    const at = (path: string, content: string) =>
+      run({ path, root: ROOT, configs: venv, content, pythonPackage: (d) => packages.has(d) });
+    const relative = "from .models import TaskList\n";
+    expect(at(`${ROOT}/src/tasks/cli.py`, relative)).toMatchObject({
+      command: `${ROOT}/.venv/bin/python`,
+      args: ["-m", "tasks.cli"],
+      cwd: "src",
+    });
+    expect(at(`${ROOT}/src/tasks/sub/__main__.py`, "from ..models import X\n")).toMatchObject({
+      args: ["-m", "tasks.sub"],
+      cwd: "src",
+    });
+    // A directory without `__init__.py` is still the module's package; a top-level one runs from the root.
+    expect(at(`${ROOT}/scripts/gen.py`, relative)).toMatchObject({ args: ["-m", "scripts.gen"], cwd: null });
+    // Without relative imports, the file runs as a script.
+    expect(at(`${ROOT}/src/tasks/cli.py`, "import argparse\n")).toMatchObject({
+      command: ".venv/bin/python",
+      args: ["src/tasks/cli.py"],
+      cwd: null,
+    });
+  });
+
   it("shell scripts: the shell of the #! line, else by extension; extensionless files by #!", () => {
     expect(run(scratch("a.sh", "#!/usr/bin/env bash\necho hi"))).toMatchObject({
       command: "/bin/bash",
diff --git a/src/features/run/producers.ts b/src/features/run/producers.ts
index c0cb58d2e..461a39d9b 100644
--- a/src/features/run/producers.ts
+++ b/src/features/run/producers.ts
@@ -55,6 +55,8 @@ export interface ContextInput {
   content?: string;
   /** Go: the module path of a module directory (`go.mod`), when known. */
   goModule?: (dir: string) => string | null | undefined;
+  /** Python: whether a directory is a package (`__init__.py`), when known. */
+  pythonPackage?: (dir: string) => boolean | undefined;
   /** 0-based caret line: the element at the caret wins over the file. */
   line?: number;
   /**
@@ -409,6 +411,31 @@ function fileConfig(
   };
 }
 
+const PYTHON_RELATIVE_IMPORT = /^\s*from\s+\.+[\w.]*\s+import\b/m;
+
+/** Whether Python source imports relatively (`from .models import X`): it only runs as a module. */
+export function hasRelativeImports(content: string | undefined): boolean {
+  return !!content && PYTHON_RELATIVE_IMPORT.test(content);
+}
+
+/**
+ * A module with relative imports, run as `python -m package.module` from the directory above
+ * its top package (its own directory is a package for the import, `__init__.py` or not).
+ */
+function pythonModule(input: ContextInput): { name: string; dir: string } | null {
+  if (!hasRelativeImports(input.content)) return null;
+  let top = dirName(input.path);
+  for (let up = dirName(top); up && up !== top && input.pythonPackage?.(up); up = dirName(up)) top = up;
+  const dir = dirName(top);
+  if (!dir || dir === top) return null;
+  const parts = input.path
+    .slice(dir === "/" ? 1 : dir.length + 1)
+    .replace(/\.py$/, "")
+    .split("/");
+  if (parts.length > 1 && (parts.at(-1) === "__init__" || parts.at(-1) === "__main__")) parts.pop();
+  return { name: parts.join("."), dir };
+}
+
 /** Python: the interpreter from settings, the detected project interpreter, then `python3` on the PATH. */
 function pythonCommand(input: ContextInput, env: ToolEnv, s: FileSite): { command: string; prefix: string[] } | null {
   if (env.python) return { command: env.python, prefix: [] };
@@ -655,6 +682,22 @@ export function produceFile(input: ContextInput, env: ToolEnv): Produced | null
     case "python": {
       const py = pythonCommand(input, env, s);
       if (!py) return { name: s.file, scope: "file", missing: missing("python", s.file, ["python3", "python"]) };
+      const module = pythonModule(input);
+      if (module) {
+        // It runs in another directory: a venv-relative interpreter is relative to the project root.
+        const command =
+          input.root && py.command.includes("/") && !py.command.startsWith("/")
+            ? `${input.root}/${py.command}`
+            : py.command;
+        return {
+          name: s.file,
+          scope: "file",
+          config: {
+            ...fileConfig(s, "python", command, [...py.prefix, "-m", module.name], "debugpy"),
+            cwd: module.dir === input.root ? null : relTo(module.dir, input.root),
+          },
+        };
+      }
       return {
         name: s.file,
         scope: "file",
diff --git a/src/features/run/pythonPackages.ts b/src/features/run/pythonPackages.ts
new file mode 100644
index 000000000..819e94a35
--- /dev/null
+++ b/src/features/run/pythonPackages.ts
@@ -0,0 +1,30 @@
+/**
+ * Which directories are Python packages (`__init__.py`), for running a module with relative
+ * imports as `python -m package.module`. Read once per directory.
+ */
+import { call, commands, isTauri } from "@/platform/ipc";
+
+const known = new Map<string, boolean>();
+
+export function invalidatePythonPackages() {
+  known.clear();
+}
+
+/** Whether `dir` is a package, when already read. */
+export function isPythonPackage(dir: string): boolean | undefined {
+  return known.get(dir);
+}
+
+const parent = (p: string) => (p.includes("/") ? p.slice(0, p.lastIndexOf("/")) || "/" : "");
+
+/** Reads the packages enclosing `path`'s directory, up to the first directory that isn't one. */
+export async function loadPythonPackages(path: string): Promise<void> {
+  if (!isTauri()) return;
+  for (let dir = parent(parent(path)); dir; dir = parent(dir)) {
+    if (!known.has(dir)) {
+      const kind = await call(commands.fsEntryKind(`${dir}/__init__.py`)).catch(() => null);
+      known.set(dir, kind === "file");
+    }
+    if (!known.get(dir) || dir === "/") return;
+  }
+}