diff --git a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_program_state.cpp b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_program_state.cpp
index 476906846793f..46ae81872fa99 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_program_state.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_program_state.cpp
@@ -2,11 +2,9 @@
 //      Check that \DexExpectProgramState correctly applies a penalty when
 //      an expected program state is never found.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: not %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -glldb" -- %s \
-// RUN:     | FileCheck %s
+// RUN: not %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expect_program_state.cpp:
 
 int GCD(int lhs, int rhs)
diff --git a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_step_kinds.cpp b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_step_kinds.cpp
index 9612c068ad611..2075cd22fa673 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_step_kinds.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_step_kinds.cpp
@@ -2,11 +2,9 @@
 //      Check that \DexExpectStepKind correctly applies a penalty when
 //      unexpected step kinds are encountered.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: not %dexter_base test --fail-lt 1.0 -w  \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// RUN: not %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expect_step_kinds.cpp:
 
 int abs(int i){
diff --git a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_step_order.cpp b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_step_order.cpp
index e52a7fffe203e..dc5f8c6b0c92b 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_step_order.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_step_order.cpp
@@ -2,11 +2,9 @@
 //      Check that \DexExpectStepOrder correctly applies a penalty for steps
 //      found out of expected order.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: not %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// RUN: not %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expect_step_order.cpp:
 
 int main()
diff --git a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_watch_type.cpp b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_watch_type.cpp
index 145eeed7ef861..838e1f87e3039 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_watch_type.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_watch_type.cpp
@@ -2,11 +2,14 @@
 //      Check that \DexExpectWatchType applies penalties when expected
 //      types are not found and unexpected types are.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: not %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+//
+// NOTE: This test passes but not in the expected way on Windows.
+// TODO: Reduce this test's coverage and be more specific about
+// expected behaviour.
+//
+// RUN: not %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expect_watch_type.cpp:
 
 template<class T>
diff --git a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_watch_value.cpp b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_watch_value.cpp
index b4c60fa321791..fa0ed119980ea 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_watch_value.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/penalty/expect_watch_value.cpp
@@ -2,11 +2,10 @@
 //      Check that \DexExpectWatchValue correctly applies a penalty when
 //      expected values are not found.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: not %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+//
+// RUN: not %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expect_watch_value.cpp:
 
 int main()
diff --git a/debuginfo-tests/dexter/feature_tests/commands/penalty/unreachable.cpp b/debuginfo-tests/dexter/feature_tests/commands/penalty/unreachable.cpp
index 5cea1c4257d0c..48f56b7d0452f 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/penalty/unreachable.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/penalty/unreachable.cpp
@@ -2,11 +2,10 @@
 //      Check that \DexUnreachable correctly applies a penalty if the command
 //      line is stepped on.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: not %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+//
+// RUN: not %dexter_regression_test -- %s | FileCheck %s
 // CHECK: unreachable.cpp:
 
 int
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_program_state.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_program_state.cpp
index ebb4766f089a8..3e77938446b07 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_program_state.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_program_state.cpp
@@ -2,11 +2,10 @@
 //      Check that \DexExpectWatchValue applies no penalties when expected
 //      program states are found.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -glldb" -- %s \
-// RUN:     | FileCheck %s
+//
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expect_program_state.cpp:
 
 int GCD(int lhs, int rhs)
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/direction.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/direction.cpp
index 3ff0e9fecbc67..1f7a96bafffae 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/direction.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/direction.cpp
@@ -5,11 +5,12 @@
 //      'VERTICAL_FORWARD' for every step onto a greater source line number in
 //      the same function.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter_base test --fail-lt 1.0 -w  \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// TODO: The dbgeng debugger does not support column step reporting at present.
+// XFAIL: system-windows
+//
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: direction.cpp:
 
 int func(int i) {
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/func.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/func.cpp
index d5ab3ffbd0367..b386dc4aa48c6 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/func.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/func.cpp
@@ -3,11 +3,9 @@
 //      trivial test. Expect one 'FUNC' per call to a function which is defined
 //      in one of the source files in the test directory.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter_base test --fail-lt 1.0 -w  \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: func.cpp:
 
 int func(int i) {
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/func_external.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/func_external.cpp
index 6dff5c8029687..cbefcb9690822 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/func_external.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/func_external.cpp
@@ -2,13 +2,13 @@
 //      Check that \DexExpectStepKind correctly counts 'FUNC_EXTERNAL' steps
 //      for a trivial test. Expect one 'FUNC_EXTERNAL' per external call.
 //
-// REQUIRES: system-linux, lldb
-// XFAIL: system-linux
-// This fails right now on my linux machine, needs examining as to why.
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter --fail-lt 1.0 -w  \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// XFAIL:*
+// This fails right now on my linux and windows machine, needs examining as to
+// why.
+//
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: func_external.cpp:
 
 #include <cstdlib>
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/recursive.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/recursive.cpp
index f2b54e4426790..0264420a46be2 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/recursive.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/recursive.cpp
@@ -3,11 +3,9 @@
 //      Specifically, ensure recursive calls count towards 'FUNC' and not
 //      'VERTICAL_BACKWARD'.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter_base test --fail-lt 1.0 -w  \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: recursive.cpp:
 
 int func(int i) {
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/small_loop.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/small_loop.cpp
index 1f9060747ec2c..fb19869f9182d 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/small_loop.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_kind/small_loop.cpp
@@ -3,11 +3,9 @@
 //      where the last source line in the loop is a call. Expect steps out
 //      of a function to a line before the call to count as 'VERTICAL_BACKWARD'.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter_base test --fail-lt 1.0 -w  \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: small_loop.cpp:
 
 int func(int i){
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_order.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_order.cpp
index a89a0cee3cc5c..cbcb5063c10f1 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_order.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_step_order.cpp
@@ -2,11 +2,9 @@
 //      Check that \DexExpectStepOrder applies no penalty when the expected
 //      order is found.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expect_step_order.cpp:
 
 int main()
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_watch_type.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_watch_type.cpp
index 41593837a9c88..67077bebcef8c 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_watch_type.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_watch_type.cpp
@@ -2,11 +2,13 @@
 //      Check that \DexExpectWatchType applies no penalties when expected
 //      types are found.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// TODO: On Windows WITH dbgeng, This test takes a long time to run and doesn't evaluate type values
+// in the same manner as LLDB.
+// XFAIL: system-windows
+//
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expect_watch_type.cpp:
 
 template<class T>
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_watch_value.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_watch_value.cpp
index 035e411369803..f22431a0900d9 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_watch_value.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/expect_watch_value.cpp
@@ -2,11 +2,9 @@
 //      Check that \DexExpectWatchValue applies no penalties when expected
 //      values are found.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expect_watch_value.cpp:
 
 unsigned long Factorial(int n) {
diff --git a/debuginfo-tests/dexter/feature_tests/commands/perfect/unreachable.cpp b/debuginfo-tests/dexter/feature_tests/commands/perfect/unreachable.cpp
index b158b4851be44..bcc1b835a6487 100644
--- a/debuginfo-tests/dexter/feature_tests/commands/perfect/unreachable.cpp
+++ b/debuginfo-tests/dexter/feature_tests/commands/perfect/unreachable.cpp
@@ -2,11 +2,9 @@
 //    Check that \DexUnreachable has no effect if the command line is never
 //    stepped on.
 //
-// REQUIRES: system-linux, lldb
+// UNSUPPORTED: system-darwin
 //
-// RUN: %dexter_base test --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: unreachable.cpp:
 
 int main()
diff --git a/debuginfo-tests/dexter/feature_tests/subtools/view.cpp b/debuginfo-tests/dexter/feature_tests/subtools/view.cpp
index 43598dbdc9b91..03e0b9420fb1d 100644
--- a/debuginfo-tests/dexter/feature_tests/subtools/view.cpp
+++ b/debuginfo-tests/dexter/feature_tests/subtools/view.cpp
@@ -1,11 +1,7 @@
 // Purpose:
 //      Check the `view` subtool works with typical inputs.
 //
-// REQUIRES: system-linux, lldb
-//
-// RUN: %dexter_base test --fail-lt 1.0 -w \
-// RUN:    --builder 'clang' --debugger 'lldb' --cflags "-O0 -g" \
-// RUN:    --results %t -- %s
+// RUN: %dexter_regression_test --results %t -- %s
 //
 // RUN: %dexter_base view %t/view.cpp.dextIR | FileCheck %s
 // CHECK: ## BEGIN
diff --git a/debuginfo-tests/lit.cfg.py b/debuginfo-tests/lit.cfg.py
index 2d93b8da9bf6d..fb2f72357b263 100644
--- a/debuginfo-tests/lit.cfg.py
+++ b/debuginfo-tests/lit.cfg.py
@@ -112,6 +112,35 @@ def get_required_attr(config, attr_name):
 dexter_base_cmd = '"{}" "{}"'.format(config.python3_executable, dexter_path)
 tools.append(ToolSubst('%dexter_base', dexter_base_cmd))
 
+# Set up commands for DexTer regression tests.
+# Builder, debugger, optimisation level and several other flags differ
+# depending on whether we're running a unix like or windows os.
+if platform.system() == 'Windows': 
+  dexter_regression_test_builder = '--builder clang-cl_vs2015'
+  dexter_regression_test_debugger = '--debugger dbgeng'
+  dexter_regression_test_cflags = '--cflags "/Zi /Od"'
+  dexter_regression_test_ldflags = '--ldflags "/Zi"'
+else:
+  dexter_regression_test_builder = '--builder clang'
+  dexter_regression_test_debugger = "--debugger lldb"
+  dexter_regression_test_cflags = '--cflags "-O0 -glldb"'
+  dexter_regression_test_ldflags = ''
+
+# Typical command would take the form:
+# ./path_to_py/python.exe ./path_to_dex/dexter.py test --fail-lt 1.0 -w --builder clang --debugger lldb --cflags '-O0 -g'
+dexter_regression_test_command = ' '.join(
+  # "python3", "dexter.py", test, fail_mode, builder, debugger, cflags, ldflags
+  ["{}".format(config.python3_executable),
+  "{}".format(dexter_path),
+  'test',
+  '--fail-lt 1.0 -w',
+  dexter_regression_test_builder,
+  dexter_regression_test_debugger,
+  dexter_regression_test_cflags,
+  dexter_regression_test_ldflags])
+
+tools.append(ToolSubst('%dexter_regression_test', dexter_regression_test_command))
+
 tool_dirs = [config.llvm_tools_dir]
 
 llvm_config.add_tool_substitutions(tools, tool_dirs)