diff --git a/llvm/tools/llvm-objcopy/CopyConfig.h b/llvm/tools/llvm-objcopy/CopyConfig.h
--- a/llvm/tools/llvm-objcopy/CopyConfig.h
+++ b/llvm/tools/llvm-objcopy/CopyConfig.h
@@ -236,10 +236,10 @@
   // success or returns an Error otherwise.
   Error parseELFConfig() {
     if (!ELF) {
-      Expected<elf::ELFCopyConfig> ELFConfig = elf::parseConfig(*this);
-      if (!ELFConfig)
+      if (Expected<elf::ELFCopyConfig> ELFConfig = elf::parseConfig(*this))
+        ELF = *ELFConfig;
+      else
         return ELFConfig.takeError();
-      ELF = *ELFConfig;
     }
     return Error::success();
   }
diff --git a/llvm/tools/llvm-objcopy/MachO/MachOObjcopy.cpp b/llvm/tools/llvm-objcopy/MachO/MachOObjcopy.cpp
--- a/llvm/tools/llvm-objcopy/MachO/MachOObjcopy.cpp
+++ b/llvm/tools/llvm-objcopy/MachO/MachOObjcopy.cpp
@@ -355,33 +355,35 @@
 Error executeObjcopyOnBinary(const CopyConfig &Config,
                              object::MachOObjectFile &In, Buffer &Out) {
   MachOReader Reader(In);
-  std::unique_ptr<Object> O = Reader.create();
-  if (!O)
-    return createFileError(
-        Config.InputFilename,
-        createStringError(object_error::parse_failed,
-                          "unable to deserialize MachO object"));
-
-  if (Error E = handleArgs(Config, *O))
-    return createFileError(Config.InputFilename, std::move(E));
-
-  // Page size used for alignment of segment sizes in Mach-O executables and
-  // dynamic libraries.
-  uint64_t PageSize;
-  switch (In.getArch()) {
-  case Triple::ArchType::arm:
-  case Triple::ArchType::aarch64:
-  case Triple::ArchType::aarch64_32:
-    PageSize = 16384;
-    break;
-  default:
-    PageSize = 4096;
-  }
+  if (Expected<std::unique_ptr<Object>> O = Reader.create()) {
+    if (!*O)
+      return createFileError(
+          Config.InputFilename,
+          createStringError(object_error::parse_failed,
+                            "unable to deserialize MachO object"));
+
+    if (Error E = handleArgs(Config, **O))
+      return createFileError(Config.InputFilename, std::move(E));
+
+    // Page size used for alignment of segment sizes in Mach-O executables and
+    // dynamic libraries.
+    uint64_t PageSize;
+    switch (In.getArch()) {
+    case Triple::ArchType::arm:
+    case Triple::ArchType::aarch64:
+    case Triple::ArchType::aarch64_32:
+      PageSize = 16384;
+      break;
+    default:
+      PageSize = 4096;
+    }
 
-  MachOWriter Writer(*O, In.is64Bit(), In.isLittleEndian(), PageSize, Out);
-  if (auto E = Writer.finalize())
-    return E;
-  return Writer.write();
+    MachOWriter Writer(**O, In.is64Bit(), In.isLittleEndian(), PageSize, Out);
+    if (auto E = Writer.finalize())
+      return E;
+    return Writer.write();
+  } else
+    return O.takeError();
 }
 
 } // end namespace macho
diff --git a/llvm/tools/llvm-objcopy/MachO/MachOReader.h b/llvm/tools/llvm-objcopy/MachO/MachOReader.h
--- a/llvm/tools/llvm-objcopy/MachO/MachOReader.h
+++ b/llvm/tools/llvm-objcopy/MachO/MachOReader.h
@@ -21,14 +21,14 @@
 class Reader {
 public:
   virtual ~Reader(){};
-  virtual std::unique_ptr<Object> create() const = 0;
+  virtual Expected<std::unique_ptr<Object>> create() const = 0;
 };
 
 class MachOReader : public Reader {
   const object::MachOObjectFile &MachOObj;
 
   void readHeader(Object &O) const;
-  void readLoadCommands(Object &O) const;
+  Error readLoadCommands(Object &O) const;
   void readSymbolTable(Object &O) const;
   void setSymbolInRelocationInfo(Object &O) const;
   void readRebaseInfo(Object &O) const;
@@ -46,7 +46,7 @@
 public:
   explicit MachOReader(const object::MachOObjectFile &Obj) : MachOObj(Obj) {}
 
-  std::unique_ptr<Object> create() const override;
+  Expected<std::unique_ptr<Object>> create() const override;
 };
 
 } // end namespace macho
diff --git a/llvm/tools/llvm-objcopy/MachO/MachOReader.cpp b/llvm/tools/llvm-objcopy/MachO/MachOReader.cpp
--- a/llvm/tools/llvm-objcopy/MachO/MachOReader.cpp
+++ b/llvm/tools/llvm-objcopy/MachO/MachOReader.cpp
@@ -59,9 +59,8 @@
   return S;
 }
 
-// TODO: get rid of reportError and make MachOReader return Expected<> instead.
 template <typename SectionType, typename SegmentType>
-std::vector<std::unique_ptr<Section>>
+Expected<std::vector<std::unique_ptr<Section>>>
 extractSections(const object::MachOObjectFile::LoadCommandInfo &LoadCmd,
                 const object::MachOObjectFile &MachOObj,
                 uint32_t &NextSectionIndex) {
@@ -86,14 +85,14 @@
     Expected<object::SectionRef> SecRef =
         MachOObj.getSection(NextSectionIndex++);
     if (!SecRef)
-      reportError(MachOObj.getFileName(), SecRef.takeError());
+      return errorWithContext(MachOObj.getFileName(), SecRef.takeError());
 
     if (Expected<ArrayRef<uint8_t>> E =
             MachOObj.getSectionContents(SecRef->getRawDataRefImpl()))
       S.Content =
           StringRef(reinterpret_cast<const char *>(E->data()), E->size());
     else
-      reportError(MachOObj.getFileName(), E.takeError());
+      return errorWithContext(MachOObj.getFileName(), E.takeError());
 
     S.Relocations.reserve(S.NReloc);
     for (auto RI = MachOObj.section_rel_begin(SecRef->getRawDataRefImpl()),
@@ -113,7 +112,7 @@
   return Sections;
 }
 
-void MachOReader::readLoadCommands(Object &O) const {
+Error MachOReader::readLoadCommands(Object &O) const {
   // For MachO sections indices start from 1.
   uint32_t NextSectionIndex = 1;
   for (auto LoadCmd : MachOObj.load_commands()) {
@@ -123,13 +122,20 @@
       O.CodeSignatureCommandIndex = O.LoadCommands.size();
       break;
     case MachO::LC_SEGMENT:
-      LC.Sections = extractSections<MachO::section, MachO::segment_command>(
-          LoadCmd, MachOObj, NextSectionIndex);
+      if (Expected<std::vector<std::unique_ptr<Section>>> Sections =
+              extractSections<MachO::section, MachO::segment_command>(
+                  LoadCmd, MachOObj, NextSectionIndex))
+        LC.Sections = std::move(*Sections);
+      else
+        return Sections.takeError();
       break;
     case MachO::LC_SEGMENT_64:
-      LC.Sections =
-          extractSections<MachO::section_64, MachO::segment_command_64>(
-              LoadCmd, MachOObj, NextSectionIndex);
+      if (Expected<std::vector<std::unique_ptr<Section>>> Sections =
+              extractSections<MachO::section_64, MachO::segment_command_64>(
+                  LoadCmd, MachOObj, NextSectionIndex))
+        LC.Sections = std::move(*Sections);
+      else
+        return Sections.takeError();
       break;
     case MachO::LC_SYMTAB:
       O.SymTabCommandIndex = O.LoadCommands.size();
@@ -177,6 +183,7 @@
     }
     O.LoadCommands.push_back(std::move(LC));
   }
+  return Error::success();
 }
 
 template <typename nlist_t>
@@ -308,10 +315,11 @@
       }
 }
 
-std::unique_ptr<Object> MachOReader::create() const {
+Expected<std::unique_ptr<Object>> MachOReader::create() const {
   auto Obj = std::make_unique<Object>();
   readHeader(*Obj);
-  readLoadCommands(*Obj);
+  if (Error E = readLoadCommands(*Obj))
+    return std::move(E);
   readSymbolTable(*Obj);
   setSymbolInRelocationInfo(*Obj);
   readRebaseInfo(*Obj);
diff --git a/llvm/tools/llvm-objcopy/llvm-objcopy.h b/llvm/tools/llvm-objcopy/llvm-objcopy.h
--- a/llvm/tools/llvm-objcopy/llvm-objcopy.h
+++ b/llvm/tools/llvm-objcopy/llvm-objcopy.h
@@ -24,6 +24,23 @@
 LLVM_ATTRIBUTE_NORETURN extern void reportError(StringRef File,
                                                 std::error_code EC);
 
+inline Error errorWithContext(StringRef Context, Error E) {
+  assert(E);
+  std::string Buf;
+  raw_string_ostream OS(Buf);
+  Optional<std::error_code> EC;
+  handleAllErrors(std::move(E), [&](const ErrorInfoBase &EI) {
+    OS << "'" + Context + "': ";
+    if (!EC)
+      EC = EI.convertToErrorCode();
+    EI.log(OS);
+    OS << "\n";
+  });
+  OS.flush();
+
+  return createStringError(*EC, Buf);
+}
+
 // This is taken from llvm-readobj.
 // [see here](llvm/tools/llvm-readobj/llvm-readobj.h:38)
 template <class T> T unwrapOrError(Expected<T> EO) {