diff --git a/docs/notes/2.26.x.md b/docs/notes/2.26.x.md
index 48835fc3540..2ae79425a7e 100644
--- a/docs/notes/2.26.x.md
+++ b/docs/notes/2.26.x.md
@@ -36,6 +36,9 @@ Some deprecations have expired and been removed:
 
 The default version of the [Pex](https://docs.pex-tool.org/) tool has been updated from 2.32.0 to [2.33.0](https://github.com/pex-tool/pex/releases/tag/v2.33.0).  Among many improvements and bug fixes, this unlocks support for pip [25.0.1](https://pip.pypa.io/en/stable/news/#v25-0-1).
 
+#### Shell
+
+The `experiemental_test_shell_command` target type may now be used with the `test` goal's `--debug` flag to execute the test interactively.
 
 #### Terraform
 
diff --git a/src/python/pants/backend/shell/goals/test.py b/src/python/pants/backend/shell/goals/test.py
index 53a850c237b..85814d7cce7 100644
--- a/src/python/pants/backend/shell/goals/test.py
+++ b/src/python/pants/backend/shell/goals/test.py
@@ -14,10 +14,18 @@
 )
 from pants.backend.shell.util_rules import shell_command
 from pants.backend.shell.util_rules.shell_command import ShellCommandProcessFromTargetRequest
-from pants.core.goals.test import TestExtraEnv, TestFieldSet, TestRequest, TestResult, TestSubsystem
+from pants.core.goals.test import (
+    TestDebugRequest,
+    TestExtraEnv,
+    TestFieldSet,
+    TestRequest,
+    TestResult,
+    TestSubsystem,
+)
 from pants.core.util_rules.environments import EnvironmentField
 from pants.engine.internals.selectors import Get
 from pants.engine.process import (
+    InteractiveProcess,
     Process,
     ProcessCacheScope,
     ProcessResultWithRetries,
@@ -46,6 +54,7 @@ def opt_out(cls, tgt: Target) -> bool:
 class ShellTestRequest(TestRequest):
     tool_subsystem = ShellTestSubsystem
     field_set_type = TestShellCommandFieldSet
+    supports_debug = True
 
 
 @rule(desc="Test with shell command", level=LogLevel.DEBUG)
@@ -88,6 +97,31 @@ async def test_shell_command(
     )
 
 
+@rule(desc="Test with shell command (interactively)", level=LogLevel.DEBUG)
+async def test_shell_command_interactively(
+    batch: ShellTestRequest.Batch[TestShellCommandFieldSet, Any],
+) -> TestDebugRequest:
+    field_set = batch.single_element
+    wrapped_tgt = await Get(
+        WrappedTarget,
+        WrappedTargetRequest(field_set.address, description_of_origin="<infallible>"),
+    )
+
+    shell_process = await Get(
+        Process,
+        ShellCommandProcessFromTargetRequest(wrapped_tgt.target),
+    )
+
+    # This is probably not strictly necessary given the use of `InteractiveProcess` but good to be correct in any event.
+    shell_process = dataclasses.replace(shell_process, cache_scope=ProcessCacheScope.PER_SESSION)
+
+    return TestDebugRequest(
+        InteractiveProcess.from_process(
+            shell_process, forward_signals_to_process=False, restartable=True
+        )
+    )
+
+
 def rules():
     return (
         *collect_rules(),
diff --git a/src/python/pants/backend/shell/goals/test_test.py b/src/python/pants/backend/shell/goals/test_test.py
index 23109cc6447..85202c4c617 100644
--- a/src/python/pants/backend/shell/goals/test_test.py
+++ b/src/python/pants/backend/shell/goals/test_test.py
@@ -17,11 +17,11 @@
 )
 from pants.build_graph.address import Address
 from pants.core.goals import package
-from pants.core.goals.test import TestResult, get_filtered_environment
+from pants.core.goals.test import TestDebugRequest, TestResult, get_filtered_environment
 from pants.core.util_rules import archive, source_files
 from pants.engine.rules import QueryRule
 from pants.engine.target import Target
-from pants.testutil.rule_runner import RuleRunner
+from pants.testutil.rule_runner import RuleRunner, mock_console
 
 ATTEMPTS_DEFAULT_OPTION = 2
 
@@ -36,6 +36,7 @@ def rule_runner() -> RuleRunner:
             *package.rules(),
             get_filtered_environment,
             QueryRule(TestResult, (ShellTestRequest.Batch,)),
+            QueryRule(TestDebugRequest, [ShellTestRequest.Batch]),
         ],
         target_types=[
             ShellSourcesGeneratorTarget,
@@ -95,11 +96,11 @@ def test_shell_command_as_test(rule_runner: RuleRunner) -> None:
     )
     (Path(rule_runner.build_root) / "test.sh").chmod(0o555)
 
+    def test_batch_for_target(test_target: Target) -> ShellTestRequest.Batch:
+        return ShellTestRequest.Batch("", (TestShellCommandFieldSet.create(test_target),), None)
+
     def run_test(test_target: Target) -> TestResult:
-        input: ShellTestRequest.Batch = ShellTestRequest.Batch(
-            "", (TestShellCommandFieldSet.create(test_target),), None
-        )
-        return rule_runner.request(TestResult, [input])
+        return rule_runner.request(TestResult, [test_batch_for_target(test_target)])
 
     pass_target = rule_runner.get_target(Address("", target_name="pass"))
     pass_result = run_test(pass_target)
@@ -111,3 +112,14 @@ def run_test(test_target: Target) -> TestResult:
     assert fail_result.exit_code == 1
     assert fail_result.stdout_bytes == b"does not contain 'xyzzy'\n"
     assert len(fail_result.process_results) == ATTEMPTS_DEFAULT_OPTION
+
+    # Check whether interactive execution via the `test` goal's `--debug` flags succeeds.
+    pass_debug_request = rule_runner.request(TestDebugRequest, [test_batch_for_target(pass_target)])
+    with mock_console(rule_runner.options_bootstrapper):
+        pass_debug_result = rule_runner.run_interactive_process(pass_debug_request.process)
+        assert pass_debug_result.exit_code == 0
+
+    fail_debug_request = rule_runner.request(TestDebugRequest, [test_batch_for_target(pass_target)])
+    with mock_console(rule_runner.options_bootstrapper):
+        fail_debug_result = rule_runner.run_interactive_process(fail_debug_request.process)
+        assert fail_debug_result.exit_code == 0