diff --git a/cli/tools/check.rs b/cli/tools/check.rs
index b41c340187..861aa87433 100644
--- a/cli/tools/check.rs
+++ b/cli/tools/check.rs
@@ -28,6 +28,7 @@ use regex::Regex;
 use crate::args::deno_json::TsConfigResolver;
 use crate::args::CheckFlags;
 use crate::args::CliOptions;
+use crate::args::DenoSubcommand;
 use crate::args::Flags;
 use crate::args::TsConfig;
 use crate::args::TsTypeLib;
@@ -94,8 +95,16 @@ pub async fn check(
 
 #[derive(Debug, thiserror::Error, deno_error::JsError)]
 #[class(type)]
-#[error("Type checking failed.")]
-pub struct FailedTypeCheckingError;
+#[error("Type checking failed.{}", if self.can_skip {
+  color_print::cstr!(
+    "\n\n  <y>info:</y> The program failed type-checking, but it still might work correctly.\n  <c>hint:</c> Re-run with <u>--no-check</u> to skip type-checking.",
+  )
+} else {
+  ""
+})]
+pub struct FailedTypeCheckingError {
+  can_skip: bool,
+}
 
 #[derive(Debug, thiserror::Error, deno_error::JsError)]
 pub enum CheckError {
@@ -199,7 +208,15 @@ impl TypeChecker {
       }
     }
     if failed {
-      Err(FailedTypeCheckingError.into())
+      Err(
+        FailedTypeCheckingError {
+          can_skip: !matches!(
+            self.cli_options.sub_command(),
+            DenoSubcommand::Check(_)
+          ),
+        }
+        .into(),
+      )
     } else {
       Ok(diagnostics.into_graph())
     }
diff --git a/tests/specs/bench/check_local_by_default2/check_local_by_default2.out b/tests/specs/bench/check_local_by_default2/check_local_by_default2.out
index 7ebc39c48a..b049816607 100644
--- a/tests/specs/bench/check_local_by_default2/check_local_by_default2.out
+++ b/tests/specs/bench/check_local_by_default2/check_local_by_default2.out
@@ -4,3 +4,6 @@ const b: "b" = 12;
     at [WILDCARD]/check_local_by_default2.ts:3:7
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/bench/no_run/no_run.out b/tests/specs/bench/no_run/no_run.out
index c048f2b1d8..92bf50709b 100644
--- a/tests/specs/bench/no_run/no_run.out
+++ b/tests/specs/bench/no_run/no_run.out
@@ -5,3 +5,6 @@ const _value: string = 1;
     at [WILDCARD]/no_run.ts:1:7
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/check/css_import/__test__.jsonc b/tests/specs/check/css_import/__test__.jsonc
index 4e16560ec2..997d815770 100644
--- a/tests/specs/check/css_import/__test__.jsonc
+++ b/tests/specs/check/css_import/__test__.jsonc
@@ -12,7 +12,7 @@
     "exitCode": 1
   }, {
     "args": "run --check not_exists.ts",
-    "output": "not_exists.out",
+    "output": "not_exists_run.out",
     "exitCode": 1
   }, {
     "args": "check exists_and_try_uses.ts",
diff --git a/tests/specs/check/css_import/not_exists_run.out b/tests/specs/check/css_import/not_exists_run.out
new file mode 100644
index 0000000000..c7dd797457
--- /dev/null
+++ b/tests/specs/check/css_import/not_exists_run.out
@@ -0,0 +1,8 @@
+Check [WILDLINE]exists.ts
+TS2307 [ERROR]: Cannot find module 'file:///[WILDLINE]/not_exists.css'.
+    at file:///[WILDLINE]/not_exists.ts:1:8
+
+error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/check/module_not_found/__test__.jsonc b/tests/specs/check/module_not_found/__test__.jsonc
index 5e7cfa2e59..16783275cc 100644
--- a/tests/specs/check/module_not_found/__test__.jsonc
+++ b/tests/specs/check/module_not_found/__test__.jsonc
@@ -7,7 +7,7 @@
     },
     "run": {
       "args": "run --check --allow-import main.ts",
-      "output": "main.out",
+      "output": "main_run.out",
       "exitCode": 1
     },
     "missing_local_root": {
diff --git a/tests/specs/check/module_not_found/main_run.out b/tests/specs/check/module_not_found/main_run.out
new file mode 100644
index 0000000000..f3baff6109
--- /dev/null
+++ b/tests/specs/check/module_not_found/main_run.out
@@ -0,0 +1,14 @@
+Download http://localhost:4545/remote.ts
+Check file:///[WILDLINE]/module_not_found/main.ts
+TS2307 [ERROR]: Cannot find module 'file:///[WILDLINE]/other.js'.
+    at file:///[WILDLINE]/main.ts:1:22
+
+TS2307 [ERROR]: Cannot find module 'http://localhost:4545/remote.ts'.
+    at file:///[WILDLINE]/main.ts:2:24
+
+Found 2 errors.
+
+error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/publish/sloppy_imports/sloppy_imports_not_enabled.out b/tests/specs/publish/sloppy_imports/sloppy_imports_not_enabled.out
index b531c0e6e2..ffa0bf5a65 100644
--- a/tests/specs/publish/sloppy_imports/sloppy_imports_not_enabled.out
+++ b/tests/specs/publish/sloppy_imports/sloppy_imports_not_enabled.out
@@ -3,3 +3,6 @@ TS2307 [ERROR]: Cannot find module 'file:///[WILDLINE]/b'. Maybe specify path to
     at file:///[WILDLINE]/mod.ts:1:20
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/_038_checkjs/038_checkjs.js.out b/tests/specs/run/_038_checkjs/038_checkjs.js.out
index 2601f27172..73c5d61489 100644
--- a/tests/specs/run/_038_checkjs/038_checkjs.js.out
+++ b/tests/specs/run/_038_checkjs/038_checkjs.js.out
@@ -22,3 +22,6 @@ const foo = new Foo();
 Found 2 errors.
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/test.js.out b/tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/test.js.out
index ad9d41c8b4..df0068f75c 100644
--- a/tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/test.js.out
+++ b/tests/specs/run/check_js_points_to_ts/check_js_points_to_ts/test.js.out
@@ -4,3 +4,6 @@ TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
     at [WILDCARD]
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/check_remote/no_check_remote.ts.disabled.out b/tests/specs/run/check_remote/no_check_remote.ts.disabled.out
index 94bab0a59b..e85bf71595 100644
--- a/tests/specs/run/check_remote/no_check_remote.ts.disabled.out
+++ b/tests/specs/run/check_remote/no_check_remote.ts.disabled.out
@@ -4,3 +4,6 @@ export const a: "a" = 12;
     at [WILDCARD]/type_error.ts:1:14
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/error_003_typescript/error_003_typescript.ts.out b/tests/specs/run/error_003_typescript/error_003_typescript.ts.out
index 58e88bbd28..1ce859a4ee 100644
--- a/tests/specs/run/error_003_typescript/error_003_typescript.ts.out
+++ b/tests/specs/run/error_003_typescript/error_003_typescript.ts.out
@@ -7,3 +7,6 @@ x = y;
     at [WILDCARD]/error_003_typescript.ts:20:1
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/error_003_typescript2/error_003_typescript.ts.out b/tests/specs/run/error_003_typescript2/error_003_typescript.ts.out
index 58e88bbd28..1ce859a4ee 100644
--- a/tests/specs/run/error_003_typescript2/error_003_typescript.ts.out
+++ b/tests/specs/run/error_003_typescript2/error_003_typescript.ts.out
@@ -7,3 +7,6 @@ x = y;
     at [WILDCARD]/error_003_typescript.ts:20:1
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/error_017_hide_long_source_ts/error_017_hide_long_source_ts.ts.out b/tests/specs/run/error_017_hide_long_source_ts/error_017_hide_long_source_ts.ts.out
index 714f654267..059b64cd84 100644
--- a/tests/specs/run/error_017_hide_long_source_ts/error_017_hide_long_source_ts.ts.out
+++ b/tests/specs/run/error_017_hide_long_source_ts/error_017_hide_long_source_ts.ts.out
@@ -3,3 +3,6 @@ TS2532 [ERROR]: Object is possibly 'undefined'.
     at [WILDCARD]/error_017_hide_long_source_ts.ts:3:1
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/error_for_await/error_for_await.ts.out b/tests/specs/run/error_for_await/error_for_await.ts.out
index 0e7a3f5d18..48cd8bf04e 100644
--- a/tests/specs/run/error_for_await/error_for_await.ts.out
+++ b/tests/specs/run/error_for_await/error_for_await.ts.out
@@ -10,3 +10,6 @@ TS1356 [ERROR]:     Did you mean to mark this function as 'async'?
         at [WILDCARD]error_for_await.ts:7:10
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/import_attributes_type_check/type_check.out b/tests/specs/run/import_attributes_type_check/type_check.out
index 5d5c95ebb7..022f5ddc16 100644
--- a/tests/specs/run/import_attributes_type_check/type_check.out
+++ b/tests/specs/run/import_attributes_type_check/type_check.out
@@ -12,3 +12,6 @@ console.log(data2.foo);
 Found 2 errors.
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/js_root_with_ts_check/js_root_with_ts_check.js.out b/tests/specs/run/js_root_with_ts_check/js_root_with_ts_check.js.out
index 09402bc381..d303c2ed83 100644
--- a/tests/specs/run/js_root_with_ts_check/js_root_with_ts_check.js.out
+++ b/tests/specs/run/js_root_with_ts_check/js_root_with_ts_check.js.out
@@ -4,3 +4,6 @@ const a = "";
     at [WILDCARD]
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/jsx_import_source/jsx_import_source_error.out b/tests/specs/run/jsx_import_source/jsx_import_source_error.out
index 0847f13ef2..3129b6744a 100644
--- a/tests/specs/run/jsx_import_source/jsx_import_source_error.out
+++ b/tests/specs/run/jsx_import_source/jsx_import_source_error.out
@@ -3,3 +3,6 @@ TS2307 [ERROR]: Cannot find module 'file:///[WILDCARD]/nonexistent/jsx-runtime'.
     at file:///[WILDLINE]/jsx_import_source_no_pragma.tsx:1:1
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/no_config_auto_discovery_for_local_script/no_auto_discovery.out b/tests/specs/run/no_config_auto_discovery_for_local_script/no_auto_discovery.out
index dbfb3d8133..9065e2a11c 100644
--- a/tests/specs/run/no_config_auto_discovery_for_local_script/no_auto_discovery.out
+++ b/tests/specs/run/no_config_auto_discovery_for_local_script/no_auto_discovery.out
@@ -4,3 +4,6 @@ TS2584 [ERROR]: Cannot find name 'document'. Do you need to change your target l
     at [WILDCARD]frontend_work.ts:2:15
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/reference_types_error/reference_types_error.js.out b/tests/specs/run/reference_types_error/reference_types_error.js.out
index 1c9e9a4b8a..7a1ceb841d 100644
--- a/tests/specs/run/reference_types_error/reference_types_error.js.out
+++ b/tests/specs/run/reference_types_error/reference_types_error.js.out
@@ -3,3 +3,6 @@ TS2307 [ERROR]: Cannot find module 'file:///[WILDLINE]/nonexistent.d.ts'.
     at file:///[WILDLINE]/reference_types_error.js:1:22
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js.out b/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js.out
index 1c9e9a4b8a..7a1ceb841d 100644
--- a/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js.out
+++ b/tests/specs/run/reference_types_error_vendor_dir/reference_types_error.js.out
@@ -3,3 +3,6 @@ TS2307 [ERROR]: Cannot find module 'file:///[WILDLINE]/nonexistent.d.ts'.
     at file:///[WILDLINE]/reference_types_error.js:1:22
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/sloppy_imports/no_sloppy.out b/tests/specs/run/sloppy_imports/no_sloppy.out
index 1f88cab635..f3c1d2b496 100644
--- a/tests/specs/run/sloppy_imports/no_sloppy.out
+++ b/tests/specs/run/sloppy_imports/no_sloppy.out
@@ -26,3 +26,6 @@ TS2307 [ERROR]: Cannot find module 'file:///[WILDLINE]/dir'. Maybe specify path
 Found 8 errors.
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/ts_type_imports/ts_type_imports.ts.out b/tests/specs/run/ts_type_imports/ts_type_imports.ts.out
index 54592beac1..7dfe46cfb3 100644
--- a/tests/specs/run/ts_type_imports/ts_type_imports.ts.out
+++ b/tests/specs/run/ts_type_imports/ts_type_imports.ts.out
@@ -6,3 +6,6 @@ const foo: Foo = new Map<string, string>();
     at [WILDCARD]ts_type_imports.ts:5:7
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/run/type_definitions_for_export/type_definitions_for_export.ts.out b/tests/specs/run/type_definitions_for_export/type_definitions_for_export.ts.out
index 4138dbf823..ab81ecda0a 100644
--- a/tests/specs/run/type_definitions_for_export/type_definitions_for_export.ts.out
+++ b/tests/specs/run/type_definitions_for_export/type_definitions_for_export.ts.out
@@ -5,3 +5,6 @@ bar(foo);
     at [WILDCARD]type_definitions_for_export.ts:7:5
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/serve/type_check/main.out b/tests/specs/serve/type_check/main.out
index b584c58985..f2463d3d67 100644
--- a/tests/specs/serve/type_check/main.out
+++ b/tests/specs/serve/type_check/main.out
@@ -5,3 +5,6 @@ TS2353 [ERROR]: Object literal may only specify known properties, and 'bad' does
     at [WILDCARD]main.ts:2:3
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/serve/type_check2/main.out b/tests/specs/serve/type_check2/main.out
index bc72afd9a5..766af20125 100644
--- a/tests/specs/serve/type_check2/main.out
+++ b/tests/specs/serve/type_check2/main.out
@@ -5,3 +5,6 @@ TS2339 [ERROR]: Property 'doesnt_exist' does not exist on type 'Request'.
     at [WILDCARD]main.ts:3:25
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/test/check_local_by_default2/main.out b/tests/specs/test/check_local_by_default2/main.out
index 92973d6919..1f73b5f00a 100644
--- a/tests/specs/test/check_local_by_default2/main.out
+++ b/tests/specs/test/check_local_by_default2/main.out
@@ -4,3 +4,6 @@ const b: "b" = 12;
     at [WILDCARD]/main.ts:3:7
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/test/doc/main.out b/tests/specs/test/doc/main.out
index 8ffc033d14..3f2e013a06 100644
--- a/tests/specs/test/doc/main.out
+++ b/tests/specs/test/doc/main.out
@@ -9,3 +9,6 @@ TS2367 [ERROR]: This comparison appears to be unintentional because the types 's
     at [WILDCARD]/main.ts$30-35.ts:3:20
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/test/markdown/main.out b/tests/specs/test/markdown/main.out
index 4536680651..c325c69435 100644
--- a/tests/specs/test/markdown/main.out
+++ b/tests/specs/test/markdown/main.out
@@ -7,3 +7,6 @@ TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
     at [WILDCARD]/main.md$29-32.ts:2:11
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/test/markdown_full_block_names/main.out b/tests/specs/test/markdown_full_block_names/main.out
index b270bfe047..adc66917ae 100644
--- a/tests/specs/test/markdown_full_block_names/main.out
+++ b/tests/specs/test/markdown_full_block_names/main.out
@@ -6,3 +6,6 @@ TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
     at [WILDCARD]/main.md$17-20.ts:2:11
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/test/markdown_ignore_html_comment/main.out b/tests/specs/test/markdown_ignore_html_comment/main.out
index cc52f5530f..de758b9bd3 100644
--- a/tests/specs/test/markdown_ignore_html_comment/main.out
+++ b/tests/specs/test/markdown_ignore_html_comment/main.out
@@ -5,3 +5,6 @@ TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
     at [WILDCARD]/main.md$34-37.ts:2:11
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/test/markdown_windows/main.out b/tests/specs/test/markdown_windows/main.out
index 4536680651..c325c69435 100644
--- a/tests/specs/test/markdown_windows/main.out
+++ b/tests/specs/test/markdown_windows/main.out
@@ -7,3 +7,6 @@ TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
     at [WILDCARD]/main.md$29-32.ts:2:11
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/test/no_run/main.out b/tests/specs/test/no_run/main.out
index 3124c7229b..e1cd887e40 100644
--- a/tests/specs/test/no_run/main.out
+++ b/tests/specs/test/no_run/main.out
@@ -5,3 +5,6 @@ const _value: string = 1;
     at [WILDCARD]/main.ts:1:7
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.
diff --git a/tests/specs/test/type_check_with_doc/main.out b/tests/specs/test/type_check_with_doc/main.out
index 54fcdade1d..21c4137fc4 100644
--- a/tests/specs/test/type_check_with_doc/main.out
+++ b/tests/specs/test/type_check_with_doc/main.out
@@ -13,3 +13,6 @@ TS2322 [ERROR]: Type 'string' is not assignable to type 'number'.
 Found 2 errors.
 
 error: Type checking failed.
+
+  info: The program failed type-checking, but it still might work correctly.
+  hint: Re-run with --no-check to skip type-checking.