diff --git a/app/models/upload.rb b/app/models/upload.rb
index a6af7a8b8699b8b79fbf65469d2894d4ac576f86..e01e9c6a4f0d41e35dde902a10230b53603cef78 100644
--- a/app/models/upload.rb
+++ b/app/models/upload.rb
@@ -12,6 +12,7 @@ class Upload < ActiveRecord::Base
   validates :uploader, presence: true
 
   scope :with_files_stored_locally, -> { where(store: ObjectStorage::Store::LOCAL) }
+  scope :with_files_stored_remotely, -> { where(store: ObjectStorage::Store::REMOTE) }
 
   before_save  :calculate_checksum!, if: :foreground_checksummable?
   after_commit :schedule_checksum,   if: :checksummable?
@@ -46,7 +47,18 @@ class Upload < ActiveRecord::Base
   end
 
   def exist?
-    File.exist?(absolute_path)
+    exist = File.exist?(absolute_path)
+
+    # Help sysadmins find missing upload files
+    if persisted? && !exist
+      if Gitlab::Sentry.enabled?
+        Raven.capture_message("Upload file does not exist", extra: self.attributes)
+      end
+
+      Gitlab::Metrics.counter(:upload_file_does_not_exist_total, 'The number of times an upload record could not find its file').increment
+    end
+
+    exist
   end
 
   def uploader_context
diff --git a/doc/administration/monitoring/prometheus/gitlab_metrics.md b/doc/administration/monitoring/prometheus/gitlab_metrics.md
index c6fd7ef7360edcbe08780cc276803e59f99cee8c..5700f640e4c006f46f00b27316df46e4a7474591 100644
--- a/doc/administration/monitoring/prometheus/gitlab_metrics.md
+++ b/doc/administration/monitoring/prometheus/gitlab_metrics.md
@@ -45,6 +45,7 @@ The following metrics are available:
 | redis_ping_success                | Gauge     | 9.4   | Whether or not the last redis ping succeeded |
 | redis_ping_latency_seconds        | Gauge     | 9.4   | Round trip time of the redis ping |
 | user_session_logins_total         | Counter   | 9.4   | Counter of how many users have logged in |
+| upload_file_does_not_exist        | Counter   | 10.7  | Number of times an upload record could not find its file |
 | failed_login_captcha_total        | Gauge | 11.0 | Counter of failed CAPTCHA attempts during login |
 | successful_login_captcha_total    | Gauge | 11.0 | Counter of successful CAPTCHA attempts during login |
 
diff --git a/spec/models/upload_spec.rb b/spec/models/upload_spec.rb
index e3544b84b502502e8347cba9d1d6544bf2bb2dac..5a0df9fbbb044b48454e9a9fe866b92c98ddc31c 100644
--- a/spec/models/upload_spec.rb
+++ b/spec/models/upload_spec.rb
@@ -112,10 +112,51 @@ describe Upload do
       expect(upload).to exist
     end
 
-    it 'returns false when the file does not exist' do
-      upload = described_class.new(path: "#{__FILE__}-nope", store: ObjectStorage::Store::LOCAL)
+    context 'when the file does not exist' do
+      it 'returns false' do
+        upload = described_class.new(path: "#{__FILE__}-nope", store: ObjectStorage::Store::LOCAL)
 
-      expect(upload).not_to exist
+        expect(upload).not_to exist
+      end
+
+      context 'when the record is persisted' do
+        it 'sends a message to Sentry' do
+          upload = create(:upload, :issuable_upload)
+
+          expect(Gitlab::Sentry).to receive(:enabled?).and_return(true)
+          expect(Raven).to receive(:capture_message).with("Upload file does not exist", extra: upload.attributes)
+
+          upload.exist?
+        end
+
+        it 'increments a metric counter to signal a problem' do
+          upload = create(:upload, :issuable_upload)
+
+          counter = double(:counter)
+          expect(counter).to receive(:increment)
+          expect(Gitlab::Metrics).to receive(:counter).with(:upload_file_does_not_exist_total, 'The number of times an upload record could not find its file').and_return(counter)
+
+          upload.exist?
+        end
+      end
+
+      context 'when the record is not persisted' do
+        it 'does not send a message to Sentry' do
+          upload = described_class.new(path: "#{__FILE__}-nope", store: ObjectStorage::Store::LOCAL)
+
+          expect(Raven).not_to receive(:capture_message)
+
+          upload.exist?
+        end
+
+        it 'does not increment a metric counter' do
+          upload = described_class.new(path: "#{__FILE__}-nope", store: ObjectStorage::Store::LOCAL)
+
+          expect(Gitlab::Metrics).not_to receive(:counter)
+
+          upload.exist?
+        end
+      end
     end
   end