diff --git a/llvm/test/tools/UpdateTestChecks/update_mc_test_checks/Inputs/error_reporting.s b/llvm/test/tools/UpdateTestChecks/update_mc_test_checks/Inputs/error_reporting.s
new file mode 100644
index 0000000000000..9f303b19c1cd7
--- /dev/null
+++ b/llvm/test/tools/UpdateTestChecks/update_mc_test_checks/Inputs/error_reporting.s
@@ -0,0 +1,3 @@
+// RUN: llvm-mc -triple=riscv64 %s | FileCheck %s
+
+add x1, x2, x3, x4
diff --git a/llvm/test/tools/UpdateTestChecks/update_mc_test_checks/error-reporting.test b/llvm/test/tools/UpdateTestChecks/update_mc_test_checks/error-reporting.test
new file mode 100644
index 0000000000000..fca1e753762b3
--- /dev/null
+++ b/llvm/test/tools/UpdateTestChecks/update_mc_test_checks/error-reporting.test
@@ -0,0 +1,11 @@
+# REQUIRES: riscv-registered-target
+## Check that update_mc_test_checks prints a useful error message with stderr when the command fails
+
+# RUN: cp -f %S/Inputs/error_reporting.s %t.s
+# RUN: not %update_mc_test_checks %t.s 2>&1 | FileCheck %s
+
+# CHECK: Error running command: {{.*}}llvm-mc{{.*}} -triple=riscv64
+# CHECK: Exit code: 1
+# CHECK: Stderr:
+# CHECK: error: expected
+# CHECK: Error: Failed to update test
diff --git a/llvm/utils/update_mc_test_checks.py b/llvm/utils/update_mc_test_checks.py
index 565e1ad085dff..d60d1c2df5e0e 100755
--- a/llvm/utils/update_mc_test_checks.py
+++ b/llvm/utils/update_mc_test_checks.py
@@ -79,17 +79,24 @@ def invoke_tool(
     if verbose:
         print("Command: ", cmd)
 
-    out = subprocess.run(
-        cmd,
-        shell=True,
-        input=full_input.encode(),
-        check=check_rc,
-        stdout=subprocess.PIPE,
-        stderr=subprocess.DEVNULL,
-    ).stdout
+    try:
+        completed = subprocess.run(
+            cmd,
+            shell=True,
+            input=full_input.encode(),
+            check=check_rc,
+            stdout=subprocess.PIPE,
+            stderr=subprocess.PIPE,
+        )
+    except subprocess.CalledProcessError as e:
+        sys.stderr.write(f"Error running command: {cmd}\n")
+        sys.stderr.write(f"Exit code: {e.returncode}\n")
+        if e.stderr:
+            sys.stderr.write(f"Stderr:\n{e.stderr.decode(errors='replace')}\n")
+        raise e
 
     # Fix line endings to unix CR style.
-    return out.decode().replace("\r\n", "\n")
+    return completed.stdout.decode().replace("\r\n", "\n")
 
 
 def isRunLine(l):