diff --git a/.changeset/honest-walls-jog.md b/.changeset/honest-walls-jog.md
new file mode 100644
index 0000000000..fa24cdf22a
--- /dev/null
+++ b/.changeset/honest-walls-jog.md
@@ -0,0 +1,6 @@
+---
+"graphile": patch
+---
+
+Don't throw error for `graphile --help` when certain libraries are not
+installed.
diff --git a/eslint.config.mjs b/eslint.config.mjs
index 88eefc9957..88508a3b94 100644
--- a/eslint.config.mjs
+++ b/eslint.config.mjs
@@ -1,4 +1,6 @@
 // @ts-check
+import { builtinModules } from "node:module";
+
 import babelParser from "@babel/eslint-parser";
 import js from "@eslint/js";
 import graphql from "@graphql-eslint/eslint-plugin";
@@ -18,6 +20,78 @@ import path from "path";
 import tseslint from "typescript-eslint";
 
 const __dirname = import.meta.dirname;
+const graphileCliRoot = "/utils/graphile/src";
+const stripAnsiPath = `${graphileCliRoot}/stripAnsi.ts`;
+const builtinModuleNames = new Set(
+  builtinModules.flatMap((name) =>
+    name.startsWith("node:") ? [name, name.slice("node:".length)] : [name],
+  ),
+);
+
+function normalizePath(filePath) {
+  return filePath.replaceAll(path.sep, "/");
+}
+
+function isGraphileCliFile(filename) {
+  const normalized = normalizePath(filename);
+  return normalized.includes(graphileCliRoot) && normalized.endsWith("/cli.ts");
+}
+
+function resolvesToAllowedRelativeImport(filename, source) {
+  if (!source.startsWith(".")) {
+    return false;
+  }
+  const resolved = normalizePath(path.resolve(path.dirname(filename), source));
+  return resolved.endsWith("/cli.ts") || resolved.endsWith(stripAnsiPath);
+}
+
+const graphileCliImportsRule = {
+  meta: {
+    type: "problem",
+    schema: [],
+  },
+  create(context) {
+    const filename = context.filename ?? context.getFilename();
+    if (!isGraphileCliFile(filename)) {
+      return {};
+    }
+
+    return {
+      ImportDeclaration(node) {
+        if (node.importKind === "type") {
+          return;
+        }
+        const source = node.source.value;
+        if (typeof source !== "string") {
+          context.report({
+            node,
+            message:
+              "Static imports in `utils/graphile/src/**/cli.ts` must use a string module specifier.",
+          });
+          return;
+        }
+        const allowed =
+          source === "graphile-config" ||
+          source.startsWith("graphile-config/") ||
+          source === "chalk" ||
+          source === "yargs" ||
+          source === "yargs/helpers" ||
+          builtinModuleNames.has(source) ||
+          resolvesToAllowedRelativeImport(filename, source);
+        if (!allowed) {
+          context.report({
+            node,
+            message:
+              "Static import '{{ source }}' is not allowed in `utils/graphile/src/**/cli.ts` because it might require software to be installed even when this command isn't invoked; use `await import(...)` inside `run()` instead.",
+            data: {
+              source,
+            },
+          });
+        }
+      },
+    };
+  },
+};
 
 const globalIgnoresFromFile = fs
   .readFileSync(path.resolve(__dirname, ".lintignore"), "utf8")
@@ -64,6 +138,11 @@ const config = {
   },
 
   plugins: {
+    crystal: {
+      rules: {
+        "graphile-cli-imports": graphileCliImportsRule,
+      },
+    },
     jest,
     "@graphql-eslint": graphql,
     tsdoc,
@@ -331,6 +410,13 @@ const oldConfig = {
       },
     },
 
+    {
+      files: ["utils/graphile/src/**/cli.ts"],
+      rules: {
+        "crystal/graphile-cli-imports": "error",
+      },
+    },
+
     // Don't use Node.js builtins
     {
       files: ["grafast/grafast/src/**", "utils/graphile-config/src/**"],
diff --git a/utils/graphile/src/commands/behavior/debug/cli.ts b/utils/graphile/src/commands/behavior/debug/cli.ts
index f3232f6ecf..e54f770c4c 100644
--- a/utils/graphile/src/commands/behavior/debug/cli.ts
+++ b/utils/graphile/src/commands/behavior/debug/cli.ts
@@ -1,7 +1,5 @@
 import type { ArgsFromOptions, Argv } from "graphile-config/cli";
 
-import { main } from "./main.ts";
-
 export function options(yargs: Argv) {
   return yargs
     .positional("entityType", { type: "string" })
@@ -19,6 +17,7 @@ export function options(yargs: Argv) {
     });
 }
 export async function run(args: ArgsFromOptions<typeof options>) {
+  const { main } = await import("./main.ts");
   const text = await main({
     config: args.config,
     entityType: args.entityType,
diff --git a/utils/graphile/src/commands/config/options/cli.ts b/utils/graphile/src/commands/config/options/cli.ts
index 50261089b2..d341eaddc6 100644
--- a/utils/graphile/src/commands/config/options/cli.ts
+++ b/utils/graphile/src/commands/config/options/cli.ts
@@ -1,7 +1,5 @@
 import type { ArgsFromOptions, Argv } from "graphile-config/cli";
 
-import { main } from "./main.ts";
-
 export const command = "options [scope]";
 
 export const description = "Output the options your config may contain";
@@ -29,7 +27,8 @@ export function options(yargs: Argv) {
       type: "string",
     });
 }
-export function run(args: ArgsFromOptions<typeof options>) {
+export async function run(args: ArgsFromOptions<typeof options>) {
+  const { main } = await import("./main.ts");
   const text = main({ filename: args.config, scope: args.scope });
   console.log(text);
 }
diff --git a/utils/graphile/src/commands/inflection/list/cli.ts b/utils/graphile/src/commands/inflection/list/cli.ts
index ea6adb506c..638fa8093d 100644
--- a/utils/graphile/src/commands/inflection/list/cli.ts
+++ b/utils/graphile/src/commands/inflection/list/cli.ts
@@ -1,7 +1,5 @@
 import type { ArgsFromOptions, Argv } from "graphile-config/cli";
 
-import { main } from "./main.ts";
-
 export function options(yargs: Argv) {
   return yargs
     .example(
@@ -21,6 +19,7 @@ export function options(yargs: Argv) {
     });
 }
 export async function run(args: ArgsFromOptions<typeof options>) {
+  const { main } = await import("./main.ts");
   const text = await main({ filename: args.config, quiet: args.quiet });
   console.log(text);
 }
diff --git a/utils/graphile/src/commands/inflection/list/main.ts b/utils/graphile/src/commands/inflection/list/main.ts
index cebae2fef0..c76230d89c 100644
--- a/utils/graphile/src/commands/inflection/list/main.ts
+++ b/utils/graphile/src/commands/inflection/list/main.ts
@@ -3,22 +3,22 @@ import path from "node:path";
 
 import chalk from "chalk";
 import type { InflectorSource } from "graphile-build";
-import { buildInflection } from "graphile-build";
 import { resolvePreset } from "graphile-config";
 import { loadConfig } from "graphile-config/load";
 import type { CompletionEntry } from "typescript";
 
 import type { ResolvedDefinition } from "../../../utils/typescriptVfs.ts";
-import {
-  accessKey,
-  configVfs,
-  prettyDocumentation,
-  prettyQuickInfoDisplayParts,
-  tightDisplayParts,
-  tightDocumentation,
-} from "../../../utils/typescriptVfs.ts";
 
 export async function main(options: { filename?: string; quiet?: boolean }) {
+  const {
+    accessKey,
+    configVfs,
+    prettyDocumentation,
+    prettyQuickInfoDisplayParts,
+    tightDisplayParts,
+    tightDocumentation,
+  } = await import("../../../utils/typescriptVfs.ts");
+  const { buildInflection } = await import("graphile-build");
   const { filename, quiet } = options;
 
   // Create inflection so we can determine where the inflectors came from