diff --git a/clang/lib/CodeGen/CGDebugInfo.cpp b/clang/lib/CodeGen/CGDebugInfo.cpp
--- a/clang/lib/CodeGen/CGDebugInfo.cpp
+++ b/clang/lib/CodeGen/CGDebugInfo.cpp
@@ -477,10 +477,8 @@
 }
 
 std::string CGDebugInfo::remapDIPath(StringRef Path) const {
-  if (DebugPrefixMap.empty())
-    return Path.str();
-
   SmallString<256> P = Path;
+  llvm::sys::path::remove_dots(P, /*remove_dot_dot=*/true);
   for (const auto &Entry : DebugPrefixMap)
     if (llvm::sys::path::replace_path_prefix(P, Entry.first, Entry.second))
       break;
diff --git a/clang/test/CodeGen/debug-info-abspath.c b/clang/test/CodeGen/debug-info-abspath.c
--- a/clang/test/CodeGen/debug-info-abspath.c
+++ b/clang/test/CodeGen/debug-info-abspath.c
@@ -5,6 +5,10 @@
 // RUN:   %t/UNIQUEISH_SENTINEL/debug-info-abspath.c -emit-llvm -o - \
 // RUN:   | FileCheck %s
 
+// RUN: %clang_cc1 -debug-info-kind=limited -triple %itanium_abi_triple \
+// RUN:   %t/UNIQUEISH_SENTINEL/../UNIQUEISH_SENTINEL/debug-info-abspath.c \
+// RUN:   -emit-llvm -o - | FileCheck %s
+
 // RUN: cp %s %t.c
 // RUN: %clang_cc1 -debug-info-kind=limited -triple %itanium_abi_triple \
 // RUN:   %t.c -emit-llvm -o - | FileCheck %s --check-prefix=INTREE
@@ -24,7 +28,7 @@
 // CHECK: = distinct !DISubprogram({{.*}}file: ![[SPFILE:[0-9]+]]
 // CHECK: ![[SPFILE]] = !DIFile(filename: "{{.*}}UNIQUEISH_SENTINEL
 // CHECK-SAME:                  debug-info-abspath.c"
-// CHECK-NOT:                   directory: "{{.*}}UNIQUEISH_SENTINEL
+// CHECK-NOT:                   directory: "{{.*}}UNIQUEISH_SENTINEL)
 
 // INTREE: = distinct !DISubprogram({{.*}}![[SPFILE:[0-9]+]]
 // INTREE: DIFile({{.*}}directory: "{{.+}}CodeGen{{.*}}")
diff --git a/clang/test/CodeGen/debug-info-relpath.c b/clang/test/CodeGen/debug-info-relpath.c
new file mode 100644
--- /dev/null
+++ b/clang/test/CodeGen/debug-info-relpath.c
@@ -0,0 +1,21 @@
+// RUN: mkdir -p %t/UNIQUEISH_SENTINEL
+// RUN: cp %s %t/UNIQUEISH_SENTINEL/debug-info-abspath.c
+// RUN: cd %t
+
+// RUN: %clang_cc1 -debug-info-kind=limited -triple %itanium_abi_triple \
+// RUN:   UNIQUEISH_SENTINEL/debug-info-abspath.c -emit-llvm -o - \
+// RUN:   | FileCheck %s
+
+// RUN: %clang_cc1 -debug-info-kind=limited -triple %itanium_abi_triple \
+// RUN:   ./UNIQUEISH_SENTINEL/../UNIQUEISH_SENTINEL/debug-info-abspath.c \
+// RUN:   -emit-llvm -o - | FileCheck %s
+
+void foo() {}
+
+// Since %s is a relative path, directory should be the common
+// prefix, but the directory part should be part of the filename.
+
+// CHECK: = distinct !DISubprogram({{.*}}file: ![[SPFILE:[0-9]+]]
+// CHECK: ![[SPFILE]] = !DIFile(filename: "UNIQUEISH_SENTINEL
+// CHECK-SAME:                  debug-info-abspath.c"
+// CHECK-NOT:                   directory: "{{.*}}UNIQUEISH_SENTINEL")
diff --git a/clang/test/CodeGenCXX/linetable-fnbegin.cpp b/clang/test/CodeGenCXX/linetable-fnbegin.cpp
--- a/clang/test/CodeGenCXX/linetable-fnbegin.cpp
+++ b/clang/test/CodeGenCXX/linetable-fnbegin.cpp
@@ -4,7 +4,7 @@
 // CHECK: define{{.*}}bar
 // CHECK-NOT: define
 // CHECK: ret {{.*}}, !dbg [[DBG:.*]]
-// CHECK: [[HPP:.*]] = !DIFile(filename: "./template.hpp",
+// CHECK: [[HPP:.*]] = !DIFile(filename: "template.hpp",
 // CHECK: [[SP:.*]] = distinct !DISubprogram(name: "bar",
 // CHECK-SAME:                               file: [[HPP]], line: 22
 // CHECK-SAME:                               DISPFlagDefinition
diff --git a/clang/test/Modules/debug-info-moduleimport.m b/clang/test/Modules/debug-info-moduleimport.m
--- a/clang/test/Modules/debug-info-moduleimport.m
+++ b/clang/test/Modules/debug-info-moduleimport.m
@@ -16,7 +16,7 @@
 // RUN:    -debugger-tuning=lldb -o - | FileCheck %s
 
 // CHECK: ![[CU:.*]] = distinct !DICompileUnit
-// CHECK-SAME:  sysroot: "/tmp/..")
+// CHECK-SAME:  sysroot: "/")
 @import DebugObjC;
 // CHECK: !DIImportedEntity(tag: DW_TAG_imported_declaration, scope: ![[CU]],
 // CHECK-SAME:              entity: ![[MODULE:.*]], file: ![[F:[0-9]+]],