diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/penalty/missing_dex_address.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/penalty/missing_dex_address.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/penalty/missing_dex_address.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/penalty/missing_dex_address.cpp
@@ -2,7 +2,8 @@
 //      Test that when a \DexDeclareAddress never resolves to a value, it is
 //      counted as a missing value in any \DexExpectWatchValues.
 //
-// REQUIRES: system-linux
+// The dbgeng driver doesn't support \DexDeclareAddress yet.
+// UNSUPPORTED: system-windows
 //
 // RUN: not %dexter_regression_test -- %s | FileCheck %s
 // CHECK: missing_dex_address.cpp
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/command_line.c b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/command_line.c
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/command_line.c
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/command_line.c
@@ -1,4 +1,5 @@
-// UNSUPPORTED: dbgeng
+// The dbgeng driver doesn't support \DexCommandLine yet.
+// UNSUPPORTED: system-windows
 //
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: command_line.c:
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/address_after_ref.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/address_after_ref.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/address_after_ref.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/address_after_ref.cpp
@@ -2,8 +2,6 @@
 //      Test that a \DexDeclareAddress value can have its value defined after
 //      the first reference to that value.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: address_after_ref.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/address_hit_count.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/address_hit_count.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/address_hit_count.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/address_hit_count.cpp
@@ -4,8 +4,6 @@
 //      expression after the target line has been stepped on a given number of
 //      times.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: address_hit_count.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/expression_address.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/expression_address.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/expression_address.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/expression_address.cpp
@@ -2,8 +2,6 @@
 //      Test that a \DexDeclareAddress value can be used to compare the
 //      addresses of two local variables that refer to the same address.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: expression_address.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/identical_address.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/identical_address.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/identical_address.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/identical_address.cpp
@@ -2,8 +2,6 @@
 //      Test that a \DexDeclareAddress value can be used to compare two equal
 //      pointer variables.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: identical_address.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/lit.local.cfg b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/lit.local.cfg
new file mode 100644
--- /dev/null
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/lit.local.cfg
@@ -0,0 +1,3 @@
+# The dbgeng driver doesn't support DexDeclareAddress yet.
+if config.is_msvc:
+    config.unsupported = True
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/multiple_address.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/multiple_address.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/multiple_address.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/multiple_address.cpp
@@ -2,8 +2,6 @@
 //      Test that multiple \DexDeclareAddress references that point to different
 //      addresses can be used within a single \DexExpectWatchValue.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: multiple_address.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/offset_address.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/offset_address.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/offset_address.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/offset_address.cpp
@@ -2,8 +2,6 @@
 //      Test that a \DexDeclareAddress value can be used to compare two pointer
 //      variables that have a fixed offset between them.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: offset_address.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/self_comparison.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/self_comparison.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/self_comparison.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_address/self_comparison.cpp
@@ -2,8 +2,6 @@
 //      Test that a \DexDeclareAddress value can be used to check the change in
 //      value of a variable over time, relative to its initial value.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: self_comparison.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_file/lit.local.cfg b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_file/lit.local.cfg
new file mode 100644
--- /dev/null
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_file/lit.local.cfg
@@ -0,0 +1,3 @@
+# FIXME: These tests compile code with %clang substitution which needs to run
+# natively but doesn't specify target triple (i.e. default triple is used).
+config.unsupported = True
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_file/precompiled_binary_different_dir/dex_commands/source_root_dir.dex b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_file/precompiled_binary_different_dir/dex_commands/source_root_dir.dex
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_file/precompiled_binary_different_dir/dex_commands/source_root_dir.dex
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_declare_file/precompiled_binary_different_dir/dex_commands/source_root_dir.dex
@@ -2,7 +2,6 @@
 ##    Check that \DexDeclareFile's file declaration can be made relative to the
 ##    --source-root-dir path.
 
-# REQUIRES: lldb
 # UNSUPPORTED: system-darwin
 
 # RUN: %clang %S/../source/test.cpp -O0 -g -o %t
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_conditional.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_conditional.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_conditional.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_conditional.cpp
@@ -1,11 +1,11 @@
+// FIXME: Feature appears to be broken on Windows with dbgeng.
+// XFAIL: system-windows
 // Purpose:
 //      Test that \DexFinishTest can be used with a condition, so the test exits
 //      when the line referenced by \DexFinishTest is stepped on and the given
 //      condition (x == 5) is satisfied.
 //      Tests using the default controller (no \DexLimitSteps).
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: default_conditional.cpp
 
@@ -15,4 +15,4 @@
 }
 
 // DexFinishTest('x', 5, on_line=ref('finish_line'))
-// DexExpectWatchValue('x', 0, 1, 2, 3, 4, 5)
+// DexExpectWatchValue('x', 0, 1, 2, 3, 4, 5, on_line=ref('finish_line'))
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_conditional_hit_count.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_conditional_hit_count.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_conditional_hit_count.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_conditional_hit_count.cpp
@@ -1,3 +1,5 @@
+// FIXME: Feature appears to be broken on Windows with dbgeng.
+// XFAIL: system-windows
 // Purpose:
 //      Test that \DexFinishTest can be used with a combination of a hit_count
 //      and a condition, so that the test exits after the line referenced
@@ -5,8 +7,6 @@
 //      given number of times.
 //      Tests using the default controller (no \DexLimitSteps).
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: default_conditional_hit_count.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_hit_count.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_hit_count.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_hit_count.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_hit_count.cpp
@@ -4,8 +4,6 @@
 //      specific number of times.
 //      Tests using the default controller (no \DexLimitSteps).
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: default_hit_count.cpp
 
@@ -15,4 +13,4 @@
 }
 
 // DexFinishTest(on_line=ref('finish_line'), hit_count=5)
-// DexExpectWatchValue('x', 0, 1, 2, 3, 4, 5)
+// DexExpectWatchValue('x', 0, 1, 2, 3, 4, 5, on_line=ref('finish_line'))
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_simple.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_simple.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_simple.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/default_simple.cpp
@@ -4,16 +4,14 @@
 //      is stepped on.
 //      Tests using the default controller (no \DexLimitSteps).
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: default_simple.cpp
 
 int main() {
-    int x = 0; // DexLabel('start_line')
-    x = 1;
+    int x = 0;
+    x = 1; // DexLabel('start_line')
     x = 2; // DexLabel('finish_line')
 }
 
 // DexFinishTest(on_line=ref('finish_line'))
-// DexExpectWatchValue('x', 0, 1)
+// DexExpectWatchValue('x', 0, 1, from_line=ref('start_line'), to_line=ref('finish_line'))
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_conditional.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_conditional.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_conditional.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_conditional.cpp
@@ -4,7 +4,8 @@
 //      condition (x == 5) is satisfied.
 //      Test using the conditional controller (using \DexLimitSteps).
 //
-// REQUIRES: system-linux
+// The dbgeng driver doesn't support \DexLimitSteps yet.
+// UNSUPPORTED: system-windows
 //
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: limit_steps_conditional.cpp
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_conditional_hit_count.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_conditional_hit_count.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_conditional_hit_count.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_conditional_hit_count.cpp
@@ -5,7 +5,8 @@
 //      given number of times.
 //      Test using the conditional controller (using \DexLimitSteps).
 //
-// REQUIRES: system-linux
+// The dbgeng driver doesn't support \DexLimitSteps yet.
+// UNSUPPORTED: system-windows
 //
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: limit_steps_conditional_hit_count.cpp
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_hit_count.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_hit_count.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_hit_count.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_hit_count.cpp
@@ -4,7 +4,8 @@
 //      specific number of times.
 //      Test using the conditional controller (using \DexLimitSteps).
 //
-// REQUIRES: system-linux
+// The dbgeng driver doesn't support \DexLimitSteps yet.
+// UNSUPPORTED: system-windows
 //
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: limit_steps_hit_count.cpp
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_simple.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_simple.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_simple.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/dex_finish_test/limit_steps_simple.cpp
@@ -4,7 +4,8 @@
 //      is stepped on.
 //      Test using the conditional controller (using \DexLimitSteps).
 //
-// REQUIRES: system-linux
+// The dbgeng driver doesn't support \DexLimitSteps yet.
+// UNSUPPORTED: system-windows
 //
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: limit_steps_simple.cpp
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/hit_count.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/hit_count.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/hit_count.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/hit_count.cpp
@@ -2,8 +2,6 @@
 //      Test that \DexLimitSteps keyword argument hit_count correctly limits
 //      the number of times the command can trigger.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: hit_count.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_check_json_step_count.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_check_json_step_count.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_check_json_step_count.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_check_json_step_count.cpp
@@ -1,8 +1,6 @@
 // Purpose:
 //      Check number of step lines are correctly reported in json output.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test --verbose -- %s | FileCheck %s
 // CHECK: limit_steps_check_json_step_count.cpp
 // CHECK: ## BEGIN ##
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_expect_loop.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_expect_loop.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_expect_loop.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_expect_loop.cpp
@@ -2,8 +2,6 @@
 //      Check the DexLimit steps only gathers step info for 2 iterations of a
 //      for loop.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: limit_steps_expect_loop.cpp:
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_expect_value.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_expect_value.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_expect_value.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_expect_value.cpp
@@ -1,8 +1,6 @@
 // Purpose:
 //      Ensure that limited stepping breaks for all expected values.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: limit_steps_expect_value.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_line_mismatch.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_line_mismatch.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_line_mismatch.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_line_mismatch.cpp
@@ -3,11 +3,6 @@
 //      doesn't exist. This can happen due to optimisations or label is on an
 //      empty line.
 //
-// FIXME: Windows regression tests run with dbgeng. \DexLimitSteps isn't yet
-// supported with dbgeng.
-//
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: limit_steps_line_mismatch.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_overlapping_ranges.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_overlapping_ranges.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_overlapping_ranges.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_overlapping_ranges.cpp
@@ -1,8 +1,6 @@
 // Purpose:
 //      Ensure that multiple overlapping \DexLimitSteps ranges do not interfere.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: limit_steps_overlapping_ranges.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_same_line_conditional.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_same_line_conditional.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_same_line_conditional.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/limit_steps_same_line_conditional.cpp
@@ -1,8 +1,6 @@
 // Purpose:
 //      Test that LimitStep commands can exist on the same from line.
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: limit_steps_same_line_conditional.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/lit.local.cfg b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/lit.local.cfg
new file mode 100644
--- /dev/null
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/lit.local.cfg
@@ -0,0 +1,4 @@
+# The dbgeng driver doesn't support DexLimitSteps yet.
+if config.is_msvc:
+    config.unsupported = True
+
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/unconditional.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/unconditional.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/unconditional.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/limit_steps/unconditional.cpp
@@ -2,8 +2,6 @@
 //      Test that \DexLimitSteps can be used without a condition (i.e. the
 //      breakpoint range is set any time from_line is stepped on).
 //
-// REQUIRES: system-linux
-//
 // RUN: %dexter_regression_test -- %s | FileCheck %s
 // CHECK: unconditional.cpp
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/lit.local.cfg b/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/lit.local.cfg
deleted file mode 100644
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/commands/perfect/lit.local.cfg
+++ /dev/null
@@ -1,2 +0,0 @@
-if not 'lldb' in config.available_features:
-    config.unsupported = True
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/clang-opt-bisect/clang-opt-bisect.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/clang-opt-bisect/clang-opt-bisect.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/clang-opt-bisect/clang-opt-bisect.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/clang-opt-bisect/clang-opt-bisect.cpp
@@ -1,12 +1,14 @@
 // Purpose:
 //     Check the `clang-opt-bisect` tool runs with typical input.
 //
-// REQUIRES: system-linux, lldb
-//
 // RUN: true
-// RUN: %dexter_base clang-opt-bisect --debugger 'lldb' --builder 'clang' \
-// RUN:     --cflags "-O0 -g" -- %s \
-// RUN:     | FileCheck %s
+// RUN: %dexter_base clang-opt-bisect \
+// RUN:     --debugger %dexter_regression_test_debugger \
+// RUN:     --builder %dexter_regression_test_builder \
+// RUN:     --cflags "%dexter_regression_test_cflags" \
+// RUN:     --ldflags "%dexter_regression_test_ldflags" \
+// RUN:     -- %s \
+// RUN: | FileCheck %s
 // CHECK: running pass 0
 // CHECK: wrote{{.*}}per_pass_score
 // CHECK: wrote{{.*}}pass-summary
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/address_printing.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/address_printing.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/address_printing.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/address_printing.cpp
@@ -8,7 +8,8 @@
 //      display the address properly; if it is implemented, this test should be
 //      updated.
 //
-// REQUIRES: lldb, system-linux
+// The dbgeng driver doesn't support \DexLimitSteps yet.
+// UNSUPPORTED: system-windows
 //
 // RUN: not %dexter_regression_test -v -- %s | FileCheck %s
 
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/err_limit_steps_no_values.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/err_limit_steps_no_values.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/err_limit_steps_no_values.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/err_limit_steps_no_values.cpp
@@ -3,8 +3,7 @@
 //    in a \DexLimitSteps command results in a useful error message.
 //    Use --binary switch to trick dexter into skipping the build step.
 //
-// REQUIRES: system-linux
 // RUN: not %dexter_base test --binary %s --debugger 'lldb' -- %s | FileCheck %s
-// CHECK: parser error:{{.*}}err_limit_steps_no_values.cpp(10): expected 0 or at least 2 positional arguments
+// CHECK: parser error:{{.*}}err_limit_steps_no_values.cpp(9): expected 0 or at least 2 positional arguments
 
 // DexLimitSteps('test')
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/label_another_line.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/label_another_line.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/label_another_line.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/label_another_line.cpp
@@ -1,6 +1,3 @@
-// REQUIRES: lldb
-// UNSUPPORTED: system-windows
-//
 // Purpose:
 //    Check that the optional keyword argument 'on_line' makes a \DexLabel label
 //    that line instead of the line the command is found on.
@@ -13,5 +10,5 @@
   return result;
 }
 
-// DexLabel('test', on_line=13)
+// DexLabel('test', on_line=10)
 // DexExpectWatchValue('result', '0', on_line=ref('test'))
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/label_offset.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/label_offset.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/label_offset.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/label_offset.cpp
@@ -1,4 +1,3 @@
-// REQUIRES: lldb
 // Purpose:
 //      Check that we can use label-relative line numbers.
 //
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/source-root-dir.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/source-root-dir.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/source-root-dir.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/test/source-root-dir.cpp
@@ -1,12 +1,10 @@
-// XFAIL:*
 // This test started failing recently for unknown reasons.
-
-// REQUIRES: lldb
-// UNSUPPORTED: system-windows
-//
+// XFAIL:*
 // RUN: %dexter --fail-lt 1.0 -w \
-// RUN:     --builder 'clang' --debugger 'lldb' \
-// RUN:     --cflags "-O0 -glldb -fdebug-prefix-map=%S=/changed" \
+// RUN:     --builder %dexter_regression_test_builder \
+// RUN:     --debugger %dexter_regression_test_debugger \
+// RUN:     --cflags "%dexter_regression_test_cflags -fdebug-prefix-map=%S=/changed" \
+// RUN:     --ldflags "%dexter_regression_test_ldflags" \
 // RUN:     --source-root-dir=%S --debugger-use-relative-paths -- %s
 
 #include <stdio.h>
diff --git a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/view.cpp b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/view.cpp
--- a/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/view.cpp
+++ b/cross-project-tests/debuginfo-tests/dexter/feature_tests/subtools/view.cpp
@@ -1,4 +1,3 @@
-// REQUIRES: lldb
 // Purpose:
 //      Check the `view` subtool works with typical inputs.
 //
diff --git a/cross-project-tests/lit.cfg.py b/cross-project-tests/lit.cfg.py
--- a/cross-project-tests/lit.cfg.py
+++ b/cross-project-tests/lit.cfg.py
@@ -111,18 +111,23 @@
   if platform.system() == 'Windows':
     # The Windows builder script uses lld.
     dependencies = ['clang', 'lld-link']
-    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"'
+    dexter_regression_test_builder = 'clang-cl_vs2015'
+    dexter_regression_test_debugger = 'dbgeng'
+    dexter_regression_test_cflags = '/Zi /Od'
+    dexter_regression_test_ldflags = '/Zi'
   else:
     # Use lldb as the debugger on non-Windows platforms.
     dependencies = ['clang', 'lldb']
-    dexter_regression_test_builder = '--builder clang'
-    dexter_regression_test_debugger = "--debugger lldb"
-    dexter_regression_test_cflags = '--cflags "-O0 -glldb"'
+    dexter_regression_test_builder = 'clang'
+    dexter_regression_test_debugger = 'lldb'
+    dexter_regression_test_cflags = '-O0 -glldb'
     dexter_regression_test_ldflags = ''
 
+  tools.append(ToolSubst('%dexter_regression_test_builder', dexter_regression_test_builder))
+  tools.append(ToolSubst('%dexter_regression_test_debugger', dexter_regression_test_debugger))
+  tools.append(ToolSubst('%dexter_regression_test_cflags', dexter_regression_test_cflags))
+  tools.append(ToolSubst('%dexter_regression_test_ldflags', dexter_regression_test_cflags))
+
   # 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'
   # Exclude build flags for %dexter_regression_base.
@@ -132,15 +137,15 @@
     '"{}"'.format(dexter_path),
     'test',
     '--fail-lt 1.0 -w',
-    dexter_regression_test_debugger])
+    '--debugger', dexter_regression_test_debugger])
   tools.append(ToolSubst('%dexter_regression_base', dexter_regression_test_base))
 
   # Include build flags for %dexter_regression_test.
   dexter_regression_test_build = ' '.join([
     dexter_regression_test_base,
-    dexter_regression_test_builder,
-    dexter_regression_test_cflags,
-    dexter_regression_test_ldflags])
+    '--builder', dexter_regression_test_builder,
+    '--cflags "',  dexter_regression_test_cflags + '"',
+    '--ldflags "', dexter_regression_test_ldflags + '"'])
   tools.append(ToolSubst('%dexter_regression_test', dexter_regression_test_build))
   return dependencies