diff --git a/lld/MachO/Config.h b/lld/MachO/Config.h
--- a/lld/MachO/Config.h
+++ b/lld/MachO/Config.h
@@ -36,6 +36,7 @@
   bool allLoad = false;
   bool forceLoadObjC = false;
   bool staticLink = false;
+  bool headerPadMaxInstallNames = false;
   uint32_t headerPad;
   llvm::StringRef installName;
   llvm::StringRef outputFile;
diff --git a/lld/MachO/Driver.cpp b/lld/MachO/Driver.cpp
--- a/lld/MachO/Driver.cpp
+++ b/lld/MachO/Driver.cpp
@@ -524,6 +524,8 @@
   config->installName =
       args.getLastArgValue(OPT_install_name, config->outputFile);
   config->headerPad = args::getHex(args, OPT_headerpad, /*Default=*/32);
+  config->headerPadMaxInstallNames =
+      args.hasArg(OPT_headerpad_max_install_names);
   config->outputType = args.hasArg(OPT_dylib) ? MH_DYLIB : MH_EXECUTE;
   config->runtimePaths = args::getStrings(args, OPT_rpath);
   config->allLoad = args.hasArg(OPT_all_load);
@@ -601,6 +603,7 @@
     case OPT_L:
     case OPT_ObjC:
     case OPT_headerpad:
+    case OPT_headerpad_max_install_names:
     case OPT_install_name:
     case OPT_rpath:
     case OPT_sub_library:
diff --git a/lld/MachO/Options.td b/lld/MachO/Options.td
--- a/lld/MachO/Options.td
+++ b/lld/MachO/Options.td
@@ -687,11 +687,10 @@
      Group<grp_rare>;
 def headerpad : Separate<["-"], "headerpad">,
      MetaVarName<"<size>">,
-     HelpText<"Allocate hex <size> extra space for future expansion of the load commands via install_name_tool">,
+     HelpText<"Allocate hex <size> extra space for future expansion of the load commands via install_name_tool (default is 0x20)">,
      Group<grp_rare>;
 def headerpad_max_install_names : Flag<["-"], "headerpad_max_install_names">,
      HelpText<"Allocate extra space so all load-command paths can expand to MAXPATHLEN via install_name_tool">,
-     Flags<[HelpHidden]>,
      Group<grp_rare>;
 def bind_at_load : Flag<["-"], "bind_at_load">,
      HelpText<"Tell dyld to bind all symbols at load time, rather than lazily">,
diff --git a/lld/MachO/Writer.cpp b/lld/MachO/Writer.cpp
--- a/lld/MachO/Writer.cpp
+++ b/lld/MachO/Writer.cpp
@@ -354,18 +354,24 @@
     seg->index = segIndex++;
   }
 
-  uint64_t dylibOrdinal = 1;
+  uint64_t dylibCount = 0;
   for (InputFile *file : inputFiles) {
     if (auto *dylibFile = dyn_cast<DylibFile>(file)) {
       in.header->addLoadCommand(
           make<LCDylib>(LC_LOAD_DYLIB, dylibFile->dylibName));
-      dylibFile->ordinal = dylibOrdinal++;
+      dylibFile->ordinal = ++dylibCount;
 
       if (dylibFile->reexport)
         in.header->addLoadCommand(
             make<LCDylib>(LC_REEXPORT_DYLIB, dylibFile->dylibName));
     }
   }
+  if (config->headerPadMaxInstallNames) {
+    size_t installNamesPadSize =
+        (dylibCount + ((config->outputType == MH_DYLIB) ? 1 : 0)) * 1024;
+    if (config->headerPad < installNamesPadSize)
+      config->headerPad = installNamesPadSize;
+  }
 }
 
 static size_t getSymbolPriority(const SymbolPriorityEntry &entry,
diff --git a/lld/test/MachO/headerpad.s b/lld/test/MachO/headerpad.s
--- a/lld/test/MachO/headerpad.s
+++ b/lld/test/MachO/headerpad.s
@@ -8,6 +8,17 @@
 ## just enforces a lower bound. We should consider implementing the same
 ## alignment behavior.
 
+# RUN: llvm-mc -filetype=obj -triple=x86_64-apple-darwin %s -o %t.o
+# RUN: lld -flavor darwinnew -o %t %t.o
+# RUN: llvm-objdump --macho --all-headers %t | FileCheck %s --check-prefix=PADN
+# PADN:      magic        cputype  cpusubtype  caps    filetype ncmds sizeofcmds               flags
+# PADN-NEXT: MH_MAGIC_64  X86_64   ALL         LIB64   EXECUTE  9     [[#%u, CMDSIZE:]] {{.*}}
+# PADN:      sectname __text
+# PADN-NEXT: segname __TEXT
+# PADN-NEXT: addr
+# PADN-NEXT: size
+# PADN-NEXT: offset [[#%u, CMDSIZE + 0x20 + 0x20]]
+
 # RUN: llvm-mc -filetype=obj -triple=x86_64-apple-darwin %s -o %t.o
 # RUN: lld -flavor darwinnew -o %t %t.o -headerpad 0
 # RUN: llvm-objdump --macho --all-headers %t | FileCheck %s --check-prefix=PAD0
@@ -17,7 +28,7 @@
 # PAD0-NEXT: segname __TEXT
 # PAD0-NEXT: addr
 # PAD0-NEXT: size
-# PAD0-NEXT: offset [[#%u, CMDSIZE + 32]]
+# PAD0-NEXT: offset [[#%u, CMDSIZE + 0x20 + 0]]
 
 # RUN: lld -flavor darwinnew -o %t %t.o -headerpad 11
 # RUN: llvm-objdump --macho --all-headers %t | FileCheck %s --check-prefix=PAD11
@@ -27,7 +38,27 @@
 # PAD11-NEXT: segname __TEXT
 # PAD11-NEXT: addr
 # PAD11-NEXT: size
-# PAD11-NEXT: offset [[#%u, CMDSIZE + 32 + 0x11]]
+# PAD11-NEXT: offset [[#%u, CMDSIZE + 0x20 + 0x11]]
+
+# RUN: lld -flavor darwinnew -o %t %t.o -headerpad_max_install_names
+# RUN: llvm-objdump --macho --all-headers %t | FileCheck %s --check-prefix=PADMAX0
+# PADMAX0:      magic        cputype  cpusubtype  caps    filetype ncmds sizeofcmds               flags
+# PADMAX0-NEXT: MH_MAGIC_64  X86_64   ALL         LIB64   EXECUTE  9     [[#%u, CMDSIZE:]] {{.*}}
+# PADMAX0:      sectname __text
+# PADMAX0-NEXT: segname __TEXT
+# PADMAX0-NEXT: addr
+# PADMAX0-NEXT: size
+# PADMAX0-NEXT: offset [[#%u, CMDSIZE + 0x20 + 0x20]]
+
+# RUN: lld -flavor darwinnew -o %t %t.o -headerpad_max_install_names -L%S/Inputs/MacOSX.sdk/usr/lib -lSystem
+# RUN: llvm-objdump --macho --all-headers %t | FileCheck %s --check-prefix=PADMAX1
+# PADMAX1:      magic        cputype  cpusubtype  caps    filetype ncmds sizeofcmds               flags
+# PADMAX1-NEXT: MH_MAGIC_64  X86_64   ALL         LIB64   EXECUTE  10     [[#%u, CMDSIZE:]] {{.*}}
+# PADMAX1:      sectname __text
+# PADMAX1-NEXT: segname __TEXT
+# PADMAX1-NEXT: addr
+# PADMAX1-NEXT: size
+# PADMAX1-NEXT: offset [[#%u, CMDSIZE + 0x20 + 0x400]]
 
 .globl _main
 _main: