diff --git a/driver/cl_options.cpp b/driver/cl_options.cpp
index 713b15b0ad..11d1544de3 100644
--- a/driver/cl_options.cpp
+++ b/driver/cl_options.cpp
@@ -223,6 +223,32 @@ cl::opt<bool> emitDwarfDebugInfo(
     "gdwarf", cl::ZeroOrMore,
     cl::desc("Emit DWARF debuginfo (instead of CodeView) for MSVC targets"));
 
+// Prefix map for filenames in DWARF debuginfo
+std::map<std::string, std::string> debugPrefixMap;
+
+struct DwarfPrefixParser : public cl::parser<std::string> {
+  explicit DwarfPrefixParser(cl::Option &O) : cl::parser<std::string>(O) {}
+
+  bool parse(cl::Option &O, llvm::StringRef /*ArgName*/, llvm::StringRef Arg,
+             std::string & /*Val*/) {
+    auto [from, to] = Arg.split('=');
+    if (from.empty() || to.empty()) {
+      return O.error("invalid debug prefix map: " + Arg);
+    }
+    auto fromStr = std::string(from);
+    if (debugPrefixMap.find(fromStr) != debugPrefixMap.end()) {
+      return O.error("debug prefix map already contains: " + fromStr);
+    }
+    debugPrefixMap[fromStr] = std::string(to);
+    return false;
+  }
+};
+
+static cl::opt<std::string, false, DwarfPrefixParser> fdebugPrefixMap(
+    "fdebug-prefix-map", cl::ZeroOrMore,
+    cl::desc("Prefix map for filenames in DWARF debuginfo"),
+    cl::value_desc("<old>=<new>"));
+
 cl::opt<bool> noAsm("noasm", cl::desc("Disallow use of inline assembler"),
                     cl::ZeroOrMore);
 
diff --git a/driver/cl_options.h b/driver/cl_options.h
index 01596ccc8e..6fe5a5b80f 100644
--- a/driver/cl_options.h
+++ b/driver/cl_options.h
@@ -21,6 +21,7 @@
 #include "llvm/Support/CodeGen.h"
 #include "llvm/Support/CommandLine.h"
 #include <deque>
+#include <map>
 #include <vector>
 
 namespace llvm {
@@ -46,6 +47,7 @@ extern cl::list<std::string> runargs;
 extern cl::opt<bool> invokedByLDMD;
 extern cl::opt<bool> compileOnly;
 extern cl::opt<bool> emitDwarfDebugInfo;
+extern std::map<std::string, std::string> debugPrefixMap; // Prefix map for filenames in DWARF debuginfo
 extern cl::opt<bool> noAsm;
 extern cl::opt<bool> dontWriteObj;
 extern cl::opt<std::string> objectFile;
diff --git a/gen/dibuilder.cpp b/gen/dibuilder.cpp
index 61ed333f7e..5c2b095aa7 100644
--- a/gen/dibuilder.cpp
+++ b/gen/dibuilder.cpp
@@ -218,27 +218,70 @@ void DIBuilder::SetValue(Loc loc, llvm::Value *value,
                                    IR->scopebb());
 }
 
+std::string DIBuilder::remapDIPath(llvm::StringRef path) {
+#if LDC_LLVM_VER >= 1800
+#define startswith starts_with
+#endif
+
+  for (const auto &[from, to] : opts::debugPrefixMap) {
+    if (path.startswith(from)) {
+      return to + path.substr(from.size()).str();
+    }
+  }
+  return std::string(path);
+
+#if LDC_LLVM_VER >= 1800
+#undef startswith
+#endif
+}
+
 DIFile DIBuilder::CreateFile(const char *filename) {
   if (!filename)
     filename = IR->dmodule->srcfile.toChars();
 
-  // clang appears to use the curent working dir as 'directory' for relative
-  // source paths, and the root path for absolute ones:
-  // clang -g -emit-llvm -S ..\blub.c =>
-  //   !DIFile(filename: "..\\blub.c", directory: "C:\\LDC\\ninja-ldc", ...)
-  //   !DIFile(filename: "Program
-  //   Files\\LLVM\\lib\\clang\\11.0.1\\include\\stddef.h", directory: "C:\\",
-  //   ...)
-
-  if (llvm::sys::path::is_absolute(filename)) {
-    return DBuilder.createFile(llvm::sys::path::relative_path(filename),
-                               llvm::sys::path::root_path(filename));
-  }
+  // Mimic clang's behavior as much as possible, including fdebug-prefix-map
+  // remap behavior. See LLVM source clang/lib/CodeGen/CGDebugInfo.cpp
+
+  auto remappedFile = remapDIPath(filename);
 
   llvm::SmallString<128> cwd;
   llvm::sys::fs::current_path(cwd);
+  auto currentDir = remapDIPath(cwd);
+
+  llvm::StringRef debuginfoDir;
+  llvm::StringRef debuginfoFile;
+
+  llvm::SmallString<128> DirBuf;
+  llvm::SmallString<128> FileBuf;
+  if (llvm::sys::path::is_absolute(remappedFile)) {
+    // Strip the common prefix (if it is more than just "/" or "C:\") from
+    // current directory and filename for a more space-efficient encoding.
+    auto FileIt = llvm::sys::path::begin(remappedFile);
+    auto FileE = llvm::sys::path::end(remappedFile);
+    auto CurDirIt = llvm::sys::path::begin(currentDir);
+    auto CurDirE = llvm::sys::path::end(currentDir);
+    for (; CurDirIt != CurDirE && *CurDirIt == *FileIt; ++CurDirIt, ++FileIt)
+      llvm::sys::path::append(DirBuf, *CurDirIt);
+    if (llvm::sys::path::root_path(DirBuf) == DirBuf) {
+      // Don't strip the common prefix if it is only the root ("/" or "C:\")
+      // since that would make diagnostic locations confusing.
+      debuginfoDir = {};
+      debuginfoFile = remappedFile;
+    } else {
+      for (; FileIt != FileE; ++FileIt)
+        llvm::sys::path::append(FileBuf, *FileIt);
+      debuginfoDir = DirBuf;
+      debuginfoFile = FileBuf;
+    }
+  } else {
+    if (!llvm::sys::path::is_absolute(filename))
+      debuginfoDir = currentDir;
+    debuginfoFile = remappedFile;
+  }
 
-  return DBuilder.createFile(filename, cwd);
+  // TODO: If debug file creation turns out to cost a lot of time, implement a
+  // caching mechanism like clang does.
+  return DBuilder.createFile(debuginfoFile, debuginfoDir);
 }
 
 DIFile DIBuilder::CreateFile(Loc loc) {
diff --git a/gen/dibuilder.h b/gen/dibuilder.h
index 01ee7d0477..2d506e38db 100644
--- a/gen/dibuilder.h
+++ b/gen/dibuilder.h
@@ -163,6 +163,7 @@ class DIBuilder {
                  llvm::SmallVector<llvm::Metadata *, 16> &elems);
   void AddStaticMembers(AggregateDeclaration *sd, ldc::DIFile file,
                  llvm::SmallVector<llvm::Metadata *, 16> &elems);
+  std::string remapDIPath(llvm::StringRef path);
   DIFile CreateFile(const char *filename = nullptr);
   DIFile CreateFile(Loc loc);
   DIFile CreateFile(Dsymbol *decl);
diff --git a/tests/debuginfo/fdebug_prefix_map.d b/tests/debuginfo/fdebug_prefix_map.d
new file mode 100644
index 0000000000..1b7ffc3e8f
--- /dev/null
+++ b/tests/debuginfo/fdebug_prefix_map.d
@@ -0,0 +1,9 @@
+// RUN: %ldc -g -fdebug-prefix-map=%S=/blablabla -output-ll -of=%t.ll %s
+// RUN: FileCheck %s < %t.ll
+
+// Check that the substitution took place. Could be as `filename: "/blablabla...` or as `directory: "/blablabla...` depending on the invoke path for lit testsuite.
+// CHECK: !DIFile({{.*}}: "/blablabla
+
+void foo()
+{
+}