diff --git a/packager/file/file.cc b/packager/file/file.cc
index 14a2f4f687..6c4933f6db 100644
--- a/packager/file/file.cc
+++ b/packager/file/file.cc
@@ -250,8 +250,10 @@ bool File::WriteStringToFile(const char* file_name,
                << contents.size() << " bytes.";
     return false;
   }
-  if (!file->Flush()) {
-    LOG(ERROR) << "Failed to flush the file '" << file_name << "'.";
+  if (!file.release()->Close()) {
+    LOG(ERROR)
+        << "Failed to close file '" << file_name
+        << "', possibly file permission issue or running out of disk space.";
     return false;
   }
   return true;
@@ -302,6 +304,12 @@ bool File::Copy(const char* from_file_name, const char* to_file_name) {
 
     total_bytes_written += bytes_written;
   }
+  if (!output_file.release()->Close()) {
+    LOG(ERROR)
+        << "Failed to close file '" << to_file_name
+        << "', possibly file permission issue or running out of disk space.";
+    return false;
+  }
   return true;
 }
 
diff --git a/packager/file/local_file.cc b/packager/file/local_file.cc
index 236f996e61..46c1dfc024 100644
--- a/packager/file/local_file.cc
+++ b/packager/file/local_file.cc
@@ -37,13 +37,25 @@ bool LocalFile::Close() {
 int64_t LocalFile::Read(void* buffer, uint64_t length) {
   DCHECK(buffer != NULL);
   DCHECK(internal_file_ != NULL);
-  return fread(buffer, sizeof(char), length, internal_file_);
+  size_t bytes_read = fread(buffer, sizeof(char), length, internal_file_);
+  VLOG(2) << "Read " << length << " return " << bytes_read << " error "
+          << ferror(internal_file_);
+  if (bytes_read == 0 && ferror(internal_file_) != 0) {
+    return -1;
+  }
+  return bytes_read;
 }
 
 int64_t LocalFile::Write(const void* buffer, uint64_t length) {
   DCHECK(buffer != NULL);
   DCHECK(internal_file_ != NULL);
-  return fwrite(buffer, sizeof(char), length, internal_file_);
+  size_t bytes_written = fwrite(buffer, sizeof(char), length, internal_file_);
+  VLOG(2) << "Write " << length << " return " << bytes_written << " error "
+          << ferror(internal_file_);
+  if (bytes_written == 0 && ferror(internal_file_) != 0) {
+    return -1;
+  }
+  return bytes_written;
 }
 
 int64_t LocalFile::Size() {
diff --git a/packager/file/threaded_io_file.cc b/packager/file/threaded_io_file.cc
index 7f668c4916..86547e3cdd 100644
--- a/packager/file/threaded_io_file.cc
+++ b/packager/file/threaded_io_file.cc
@@ -58,13 +58,14 @@ bool ThreadedIoFile::Open() {
 bool ThreadedIoFile::Close() {
   DCHECK(internal_file_);
 
+  bool result = true;
   if (mode_ == kOutputMode)
-    Flush();
+    result = Flush();
 
   cache_.Close();
   task_exit_event_.Wait();
 
-  bool result = internal_file_.release()->Close();
+  result &= internal_file_.release()->Close();
   delete this;
   return result;
 }
@@ -110,6 +111,9 @@ bool ThreadedIoFile::Flush() {
   DCHECK(internal_file_);
   DCHECK_EQ(kOutputMode, mode_);
 
+  if (NoBarrier_Load(&internal_file_error_))
+    return false;
+
   flushing_ = true;
   cache_.Close();
   flush_complete_event_.Wait();
@@ -204,6 +208,10 @@ void ThreadedIoFile::RunInOutputMode() {
         if (write_result < 0) {
           NoBarrier_Store(&internal_file_error_, write_result);
           cache_.Close();
+          if (flushing_) {
+            flushing_ = false;
+            flush_complete_event_.Signal();
+          }
           return;
         }
         bytes_written += write_result;
diff --git a/packager/media/formats/mp4/single_segment_segmenter.cc b/packager/media/formats/mp4/single_segment_segmenter.cc
index d4be794201..1433a90310 100644
--- a/packager/media/formats/mp4/single_segment_segmenter.cc
+++ b/packager/media/formats/mp4/single_segment_segmenter.cc
@@ -90,8 +90,10 @@ Status SingleSegmentSegmenter::DoFinalize() {
 
   // Close the temp file to prepare for reading later.
   if (!temp_file_.release()->Close()) {
-    return Status(error::FILE_FAILURE,
-                  "Cannot close the temp file " + temp_file_name_);
+    return Status(
+        error::FILE_FAILURE,
+        "Cannot close the temp file " + temp_file_name_ +
+            ", possibly file permission issue or running out of disk space.");
   }
 
   std::unique_ptr<File, FileCloser> file(
@@ -142,6 +144,16 @@ Status SingleSegmentSegmenter::DoFinalize() {
     UpdateProgress(static_cast<double>(size) / temp_file->Size() *
                    re_segment_progress_target);
   }
+  if (!temp_file.release()->Close()) {
+    return Status(error::FILE_FAILURE, "Cannot close the temp file " +
+                                           temp_file_name_ + " after reading.");
+  }
+  if (!file.release()->Close()) {
+    return Status(
+        error::FILE_FAILURE,
+        "Cannot close file " + options().output_file_name +
+            ", possibly file permission issue or running out of disk space.");
+  }
   SetComplete();
   return Status::OK;
 }
diff --git a/packager/media/formats/webm/mkv_writer.cc b/packager/media/formats/webm/mkv_writer.cc
index d77bcf74c5..0d919d0ac6 100644
--- a/packager/media/formats/webm/mkv_writer.cc
+++ b/packager/media/formats/webm/mkv_writer.cc
@@ -29,7 +29,10 @@ Status MkvWriter::Open(const std::string& name) {
 Status MkvWriter::Close() {
   const std::string file_name = file_->file_name();
   if (!file_.release()->Close()) {
-    return Status(error::FILE_FAILURE, "Cannot close file " + file_name);
+    return Status(
+        error::FILE_FAILURE,
+        "Cannot close file " + file_name +
+            ", possibly file permission issue or running out of disk space.");
   }
   return Status::OK;
 }