diff --git a/app/app.go b/app/app.go
index 5998105200..bf167d35e3 100644
--- a/app/app.go
+++ b/app/app.go
@@ -154,9 +154,9 @@ func (a *App) Handle404(w http.ResponseWriter, r *http.Request) {
 }
 
 func (s *Server) getSystemInstallDate() (int64, *model.AppError) {
-	systemData, appErr := s.Store.System().GetByName(model.SYSTEM_INSTALLATION_DATE_KEY)
-	if appErr != nil {
-		return 0, appErr
+	systemData, err := s.Store.System().GetByName(model.SYSTEM_INSTALLATION_DATE_KEY)
+	if err != nil {
+		return 0, model.NewAppError("getSystemInstallDate", "app.system.get_by_name.app_error", nil, err.Error(), http.StatusInternalServerError)
 	}
 	value, err := strconv.ParseInt(systemData.Value, 10, 64)
 	if err != nil {
@@ -166,9 +166,9 @@ func (s *Server) getSystemInstallDate() (int64, *model.AppError) {
 }
 
 func (s *Server) getFirstServerRunTimestamp() (int64, *model.AppError) {
-	systemData, appErr := s.Store.System().GetByName(model.SYSTEM_FIRST_SERVER_RUN_TIMESTAMP_KEY)
-	if appErr != nil {
-		return 0, appErr
+	systemData, err := s.Store.System().GetByName(model.SYSTEM_FIRST_SERVER_RUN_TIMESTAMP_KEY)
+	if err != nil {
+		return 0, model.NewAppError("getFirstServerRunTimestamp", "app.system.get_by_name.app_error", nil, err.Error(), http.StatusInternalServerError)
 	}
 	value, err := strconv.ParseInt(systemData.Value, 10, 64)
 	if err != nil {
@@ -178,9 +178,9 @@ func (s *Server) getFirstServerRunTimestamp() (int64, *model.AppError) {
 }
 
 func (a *App) GetWarnMetricsStatus() (map[string]*model.WarnMetricStatus, *model.AppError) {
-	systemDataList, appErr := a.Srv().Store.System().Get()
-	if appErr != nil {
-		return nil, appErr
+	systemDataList, nErr := a.Srv().Store.System().Get()
+	if nErr != nil {
+		return nil, model.NewAppError("GetWarnMetricsStatus", "app.system.get.app_error", nil, nErr.Error(), http.StatusInternalServerError)
 	}
 
 	result := map[string]*model.WarnMetricStatus{}
@@ -345,8 +345,8 @@ func (a *App) notifyAdminsOfWarnMetricStatus(warnMetricId string) *model.AppErro
 
 func (a *App) NotifyAndSetWarnMetricAck(warnMetricId string, sender *model.User, forceAck bool, isBot bool) *model.AppError {
 	if warnMetric, ok := model.WarnMetricsTable[warnMetricId]; ok {
-		data, err := a.Srv().Store.System().GetByName(warnMetric.Id)
-		if err == nil && data != nil && data.Value == model.WARN_METRIC_STATUS_ACK {
+		data, nErr := a.Srv().Store.System().GetByName(warnMetric.Id)
+		if nErr == nil && data != nil && data.Value == model.WARN_METRIC_STATUS_ACK {
 			mlog.Debug("This metric warning has already been acknowledged")
 			return nil
 		}
@@ -384,14 +384,14 @@ func (a *App) NotifyAndSetWarnMetricAck(warnMetricId string, sender *model.User,
 			subject := T("api.templates.warn_metric_ack.subject")
 			bodyPage.Props["Title"] = warnMetricDisplayTexts.EmailBody
 
-			if err = mailservice.SendMailUsingConfig(model.MM_SUPPORT_ADDRESS, subject, bodyPage.Render(), a.Config(), false, sender.Email); err != nil {
+			if err := mailservice.SendMailUsingConfig(model.MM_SUPPORT_ADDRESS, subject, bodyPage.Render(), a.Config(), false, sender.Email); err != nil {
 				mlog.Error("Error while sending email", mlog.String("destination email", model.MM_SUPPORT_ADDRESS), mlog.Err(err))
 				return model.NewAppError("NotifyAndSetWarnMetricAck", "api.email.send_warn_metric_ack.failure.app_error", map[string]interface{}{"Error": err.Error()}, "", http.StatusInternalServerError)
 			}
 		}
 
 		mlog.Debug("Disable the monitoring of all warn metrics")
-		err = a.setWarnMetricsStatus(model.WARN_METRIC_STATUS_ACK)
+		err := a.setWarnMetricsStatus(model.WARN_METRIC_STATUS_ACK)
 		if err != nil {
 			return err
 		}
diff --git a/app/config.go b/app/config.go
index e5edfe6997..588a2e706b 100644
--- a/app/config.go
+++ b/app/config.go
@@ -139,8 +139,8 @@ func (s *Server) ensurePostActionCookieSecret() error {
 		}
 		system.Value = string(v)
 		// If we were able to save the key, use it, otherwise log the error.
-		if appErr := s.Store.System().Save(system); appErr != nil {
-			mlog.Error("Failed to save PostActionCookieSecret", mlog.Err(appErr))
+		if err = s.Store.System().Save(system); err != nil {
+			mlog.Error("Failed to save PostActionCookieSecret", mlog.Err(err))
 		} else {
 			secret = newSecret
 		}
@@ -202,8 +202,8 @@ func (s *Server) ensureAsymmetricSigningKey() error {
 		}
 		system.Value = string(v)
 		// If we were able to save the key, use it, otherwise log the error.
-		if appErr := s.Store.System().Save(system); appErr != nil {
-			mlog.Error("Failed to save AsymmetricSigningKey", mlog.Err(appErr))
+		if err = s.Store.System().Save(system); err != nil {
+			mlog.Error("Failed to save AsymmetricSigningKey", mlog.Err(err))
 		} else {
 			key = newKey
 		}
@@ -242,40 +242,38 @@ func (s *Server) ensureAsymmetricSigningKey() error {
 }
 
 func (s *Server) ensureInstallationDate() error {
-	_, err := s.getSystemInstallDate()
-	if err == nil {
+	_, appErr := s.getSystemInstallDate()
+	if appErr == nil {
 		return nil
 	}
 
-	installDate, err := s.Store.User().InferSystemInstallDate()
+	installDate, appErr := s.Store.User().InferSystemInstallDate()
 	var installationDate int64
-	if err == nil && installDate > 0 {
+	if appErr == nil && installDate > 0 {
 		installationDate = installDate
 	} else {
 		installationDate = utils.MillisFromTime(time.Now())
 	}
 
-	err = s.Store.System().SaveOrUpdate(&model.System{
+	if err := s.Store.System().SaveOrUpdate(&model.System{
 		Name:  model.SYSTEM_INSTALLATION_DATE_KEY,
 		Value: strconv.FormatInt(installationDate, 10),
-	})
-	if err != nil {
+	}); err != nil {
 		return err
 	}
 	return nil
 }
 
 func (s *Server) ensureFirstServerRunTimestamp() error {
-	_, err := s.getFirstServerRunTimestamp()
-	if err == nil {
+	_, appErr := s.getFirstServerRunTimestamp()
+	if appErr == nil {
 		return nil
 	}
 
-	err = s.Store.System().SaveOrUpdate(&model.System{
+	if err := s.Store.System().SaveOrUpdate(&model.System{
 		Name:  model.SYSTEM_FIRST_SERVER_RUN_TIMESTAMP_KEY,
 		Value: strconv.FormatInt(utils.MillisFromTime(time.Now()), 10),
-	})
-	if err != nil {
+	}); err != nil {
 		return err
 	}
 	return nil
diff --git a/app/diagnostics.go b/app/diagnostics.go
index 50eb750806..2bbe8979b3 100644
--- a/app/diagnostics.go
+++ b/app/diagnostics.go
@@ -1043,8 +1043,8 @@ func (s *Server) trackChannelModeration() {
 }
 
 func (s *Server) trackWarnMetrics() {
-	systemDataList, appErr := s.Store.System().Get()
-	if appErr != nil {
+	systemDataList, nErr := s.Store.System().Get()
+	if nErr != nil {
 		return
 	}
 	for key, value := range systemDataList {
diff --git a/app/license.go b/app/license.go
index e5d656748d..016c5161b0 100644
--- a/app/license.go
+++ b/app/license.go
@@ -31,8 +31,8 @@ func (s *Server) LoadLicense() {
 	}
 
 	licenseId := ""
-	props, err := s.Store.System().Get()
-	if err == nil {
+	props, nErr := s.Store.System().Get()
+	if nErr == nil {
 		licenseId = props[model.SYSTEM_ACTIVE_LICENSE_ID]
 	}
 
@@ -41,7 +41,7 @@ func (s *Server) LoadLicense() {
 		license, licenseBytes := utils.GetAndValidateLicenseFileFromDisk(*s.Config().ServiceSettings.LicenseFileLocation)
 
 		if license != nil {
-			if _, err = s.SaveLicense(licenseBytes); err != nil {
+			if _, err := s.SaveLicense(licenseBytes); err != nil {
 				mlog.Info("Failed to save license key loaded from disk.", mlog.Err(err))
 			} else {
 				licenseId = license.Id
@@ -184,7 +184,7 @@ func (s *Server) RemoveLicense() *model.AppError {
 	sysVar.Value = ""
 
 	if err := s.Store.System().SaveOrUpdate(sysVar); err != nil {
-		return err
+		return model.NewAppError("RemoveLicense", "app.system.save.app_error", nil, err.Error(), http.StatusInternalServerError)
 	}
 
 	s.SetLicense(nil)
diff --git a/app/permissions.go b/app/permissions.go
index d0281c6bef..9b719f3d8a 100644
--- a/app/permissions.go
+++ b/app/permissions.go
@@ -55,17 +55,17 @@ func (a *App) ResetPermissionsSystem() *model.AppError {
 
 	// Remove the "System" table entry that marks the advanced permissions migration as done.
 	if _, err := a.Srv().Store.System().PermanentDeleteByName(ADVANCED_PERMISSIONS_MIGRATION_KEY); err != nil {
-		return err
+		return model.NewAppError("ResetPermissionSystem", "app.system.permanent_delete_by_name.app_error", nil, err.Error(), http.StatusInternalServerError)
 	}
 
 	// Remove the "System" table entry that marks the emoji permissions migration as done.
 	if _, err := a.Srv().Store.System().PermanentDeleteByName(EMOJIS_PERMISSIONS_MIGRATION_KEY); err != nil {
-		return err
+		return model.NewAppError("ResetPermissionSystem", "app.system.permanent_delete_by_name.app_error", nil, err.Error(), http.StatusInternalServerError)
 	}
 
 	// Remove the "System" table entry that marks the guest roles permissions migration as done.
 	if _, err := a.Srv().Store.System().PermanentDeleteByName(GUEST_ROLES_CREATION_MIGRATION_KEY); err != nil {
-		return err
+		return model.NewAppError("ResetPermissionSystem", "app.system.permanent_delete_by_name.app_error", nil, err.Error(), http.StatusInternalServerError)
 	}
 
 	// Now that the permissions system has been reset, re-run the migration to reinitialise it.
diff --git a/app/permissions_migrations.go b/app/permissions_migrations.go
index 99b76edbd2..0062723c27 100644
--- a/app/permissions_migrations.go
+++ b/app/permissions_migrations.go
@@ -176,7 +176,7 @@ func (a *App) doPermissionsMigration(key string, migrationMap permissionsMap) *m
 	}
 
 	if err := a.Srv().Store.System().Save(&model.System{Name: key, Value: "true"}); err != nil {
-		return err
+		return model.NewAppError("doPermissionsMigration", "app.system.save.app_error", nil, err.Error(), http.StatusInternalServerError)
 	}
 	return nil
 }
diff --git a/app/server.go b/app/server.go
index 71ed789672..ba86aab7ac 100644
--- a/app/server.go
+++ b/app/server.go
@@ -1152,14 +1152,14 @@ func doCheckNumberOfActiveUsersWarnMetricStatus(a *App) {
 	}
 
 	for _, warnMetric := range warnMetrics {
-		data, err := a.Srv().Store.System().GetByName(warnMetric.Id)
-		if err == nil && data != nil && (data.Value == model.WARN_METRIC_STATUS_ACK || data.Value == model.WARN_METRIC_STATUS_RUNONCE) {
+		data, nErr := a.Srv().Store.System().GetByName(warnMetric.Id)
+		if nErr == nil && data != nil && (data.Value == model.WARN_METRIC_STATUS_ACK || data.Value == model.WARN_METRIC_STATUS_RUNONCE) {
 			mlog.Debug("This metric warning has already been acked or should only run once")
 			continue
 		}
 
-		if err = a.Srv().Store.System().SaveOrUpdate(&model.System{Name: warnMetric.Id, Value: model.WARN_METRIC_STATUS_LIMIT_REACHED}); err != nil {
-			mlog.Error("Unable to write to database.", mlog.String("id", warnMetric.Id), mlog.Err(err))
+		if nErr = a.Srv().Store.System().SaveOrUpdate(&model.System{Name: warnMetric.Id, Value: model.WARN_METRIC_STATUS_LIMIT_REACHED}); nErr != nil {
+			mlog.Error("Unable to write to database.", mlog.String("id", warnMetric.Id), mlog.Err(nErr))
 			continue
 		}
 		warnMetricStatus, _ := a.getWarnMetricStatusAndDisplayTextsForId(warnMetric.Id, nil)
diff --git a/i18n/en.json b/i18n/en.json
index f0eed1a5c3..add982db05 100644
--- a/i18n/en.json
+++ b/i18n/en.json
@@ -4470,6 +4470,22 @@
     "id": "app.submit_interactive_dialog.json_error",
     "translation": "Encountered an error encoding JSON for the interactive dialog."
   },
+  {
+    "id": "app.system.get.app_error",
+    "translation": "We encountered an error finding the system properties."
+  },
+  {
+    "id": "app.system.get_by_name.app_error",
+    "translation": "Unable to find the system variable."
+  },
+  {
+    "id": "app.system.permanent_delete_by_name.app_error",
+    "translation": "We could not permanently delete the system table entry."
+  },
+  {
+    "id": "app.system.save.app_error",
+    "translation": "We encountered an error saving the system property."
+  },
   {
     "id": "app.system.warn_metric.bot_description",
     "translation": "[Learn more about the Mattermost Advisor](https://about.mattermost.com/default-channel-handle-documentation)"
@@ -5502,6 +5518,10 @@
     "id": "mfa.validate_token.authenticate.app_error",
     "translation": "Invalid MFA token."
   },
+  {
+    "id": "migrations.system.save.app_error",
+    "translation": "We encountered an error saving the system property."
+  },
   {
     "id": "migrations.worker.run_advanced_permissions_phase_2_migration.invalid_progress",
     "translation": "Migration failed due to invalid progress data."
@@ -7310,30 +7330,6 @@
     "id": "store.sql_post.search.disabled",
     "translation": "Searching has been disabled on this server. Please contact your System Administrator."
   },
-  {
-    "id": "store.sql_system.get.app_error",
-    "translation": "We encountered an error finding the system properties."
-  },
-  {
-    "id": "store.sql_system.get_by_name.app_error",
-    "translation": "Unable to find the system variable."
-  },
-  {
-    "id": "store.sql_system.permanent_delete_by_name.app_error",
-    "translation": "We could not permanently delete the system table entry."
-  },
-  {
-    "id": "store.sql_system.save.app_error",
-    "translation": "We encountered an error saving the system property."
-  },
-  {
-    "id": "store.sql_system.save.commit_transaction.app_error",
-    "translation": "Failed to commit the database transaction."
-  },
-  {
-    "id": "store.sql_system.update.app_error",
-    "translation": "We encountered an error updating the system property."
-  },
   {
     "id": "store.sql_team.analytics_get_team_count_for_scheme.app_error",
     "translation": "Unable to get the channel count for the scheme."
diff --git a/migrations/migrations_test.go b/migrations/migrations_test.go
index e2227c5abd..4075b56895 100644
--- a/migrations/migrations_test.go
+++ b/migrations/migrations_test.go
@@ -34,16 +34,16 @@ func TestGetMigrationState(t *testing.T) {
 		Name:  migrationKey,
 		Value: "true",
 	}
-	err = th.App.Srv().Store.System().Save(&system)
-	assert.Nil(t, err)
+	nErr := th.App.Srv().Store.System().Save(&system)
+	assert.Nil(t, nErr)
 
 	state, job, err = GetMigrationState(migrationKey, th.App.Srv().Store)
 	assert.Nil(t, err)
 	assert.Nil(t, job)
 	assert.Equal(t, "completed", state)
 
-	_, err = th.App.Srv().Store.System().PermanentDeleteByName(migrationKey)
-	assert.Nil(t, err)
+	_, nErr = th.App.Srv().Store.System().PermanentDeleteByName(migrationKey)
+	assert.Nil(t, nErr)
 
 	// Test with a job scheduled in "pending" state.
 	j1 := &model.Job{
diff --git a/migrations/worker.go b/migrations/worker.go
index f1067aaea7..a4386a66d0 100644
--- a/migrations/worker.go
+++ b/migrations/worker.go
@@ -157,8 +157,8 @@ func (worker *Worker) runMigration(key string, lastDone string) (bool, string, *
 	}
 
 	if done {
-		if saveErr := worker.srv.Store.System().Save(&model.System{Name: key, Value: "true"}); saveErr != nil {
-			return false, "", saveErr
+		if nErr := worker.srv.Store.System().Save(&model.System{Name: key, Value: "true"}); nErr != nil {
+			return false, "", model.NewAppError("runMigration", "migrations.system.save.app_error", nil, nErr.Error(), http.StatusInternalServerError)
 		}
 	}
 
diff --git a/store/opentracinglayer/opentracinglayer.go b/store/opentracinglayer/opentracinglayer.go
index b3e14486a6..09258cf832 100644
--- a/store/opentracinglayer/opentracinglayer.go
+++ b/store/opentracinglayer/opentracinglayer.go
@@ -6332,7 +6332,7 @@ func (s *OpenTracingLayerStatusStore) UpdateLastActivityAt(userId string, lastAc
 	return err
 }
 
-func (s *OpenTracingLayerSystemStore) Get() (model.StringMap, *model.AppError) {
+func (s *OpenTracingLayerSystemStore) Get() (model.StringMap, error) {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "SystemStore.Get")
 	s.Root.Store.SetContext(newCtx)
@@ -6350,7 +6350,7 @@ func (s *OpenTracingLayerSystemStore) Get() (model.StringMap, *model.AppError) {
 	return result, err
 }
 
-func (s *OpenTracingLayerSystemStore) GetByName(name string) (*model.System, *model.AppError) {
+func (s *OpenTracingLayerSystemStore) GetByName(name string) (*model.System, error) {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "SystemStore.GetByName")
 	s.Root.Store.SetContext(newCtx)
@@ -6368,7 +6368,7 @@ func (s *OpenTracingLayerSystemStore) GetByName(name string) (*model.System, *mo
 	return result, err
 }
 
-func (s *OpenTracingLayerSystemStore) InsertIfExists(system *model.System) (*model.System, *model.AppError) {
+func (s *OpenTracingLayerSystemStore) InsertIfExists(system *model.System) (*model.System, error) {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "SystemStore.InsertIfExists")
 	s.Root.Store.SetContext(newCtx)
@@ -6386,7 +6386,7 @@ func (s *OpenTracingLayerSystemStore) InsertIfExists(system *model.System) (*mod
 	return result, err
 }
 
-func (s *OpenTracingLayerSystemStore) PermanentDeleteByName(name string) (*model.System, *model.AppError) {
+func (s *OpenTracingLayerSystemStore) PermanentDeleteByName(name string) (*model.System, error) {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "SystemStore.PermanentDeleteByName")
 	s.Root.Store.SetContext(newCtx)
@@ -6404,7 +6404,7 @@ func (s *OpenTracingLayerSystemStore) PermanentDeleteByName(name string) (*model
 	return result, err
 }
 
-func (s *OpenTracingLayerSystemStore) Save(system *model.System) *model.AppError {
+func (s *OpenTracingLayerSystemStore) Save(system *model.System) error {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "SystemStore.Save")
 	s.Root.Store.SetContext(newCtx)
@@ -6422,7 +6422,7 @@ func (s *OpenTracingLayerSystemStore) Save(system *model.System) *model.AppError
 	return err
 }
 
-func (s *OpenTracingLayerSystemStore) SaveOrUpdate(system *model.System) *model.AppError {
+func (s *OpenTracingLayerSystemStore) SaveOrUpdate(system *model.System) error {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "SystemStore.SaveOrUpdate")
 	s.Root.Store.SetContext(newCtx)
@@ -6440,7 +6440,7 @@ func (s *OpenTracingLayerSystemStore) SaveOrUpdate(system *model.System) *model.
 	return err
 }
 
-func (s *OpenTracingLayerSystemStore) Update(system *model.System) *model.AppError {
+func (s *OpenTracingLayerSystemStore) Update(system *model.System) error {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "SystemStore.Update")
 	s.Root.Store.SetContext(newCtx)
diff --git a/store/retrylayer/retrylayer.go b/store/retrylayer/retrylayer.go
index 5b0b907a6d..b0fc19b959 100644
--- a/store/retrylayer/retrylayer.go
+++ b/store/retrylayer/retrylayer.go
@@ -4630,45 +4630,143 @@ func (s *RetryLayerStatusStore) UpdateLastActivityAt(userId string, lastActivity
 
 }
 
-func (s *RetryLayerSystemStore) Get() (model.StringMap, *model.AppError) {
+func (s *RetryLayerSystemStore) Get() (model.StringMap, error) {
 
-	return s.SystemStore.Get()
+	tries := 0
+	for {
+		result, err := s.SystemStore.Get()
+		if err == nil {
+			return result, err
+		}
+		if !isRepeatableError(err) {
+			return result, err
+		}
+		tries++
+		if tries >= 3 {
+			err = errors.Wrap(err, "giving up after 3 consecutive repeatable transaction failures")
+			return result, err
+		}
+	}
 
 }
 
-func (s *RetryLayerSystemStore) GetByName(name string) (*model.System, *model.AppError) {
+func (s *RetryLayerSystemStore) GetByName(name string) (*model.System, error) {
 
-	return s.SystemStore.GetByName(name)
+	tries := 0
+	for {
+		result, err := s.SystemStore.GetByName(name)
+		if err == nil {
+			return result, err
+		}
+		if !isRepeatableError(err) {
+			return result, err
+		}
+		tries++
+		if tries >= 3 {
+			err = errors.Wrap(err, "giving up after 3 consecutive repeatable transaction failures")
+			return result, err
+		}
+	}
 
 }
 
-func (s *RetryLayerSystemStore) InsertIfExists(system *model.System) (*model.System, *model.AppError) {
+func (s *RetryLayerSystemStore) InsertIfExists(system *model.System) (*model.System, error) {
 
-	return s.SystemStore.InsertIfExists(system)
+	tries := 0
+	for {
+		result, err := s.SystemStore.InsertIfExists(system)
+		if err == nil {
+			return result, err
+		}
+		if !isRepeatableError(err) {
+			return result, err
+		}
+		tries++
+		if tries >= 3 {
+			err = errors.Wrap(err, "giving up after 3 consecutive repeatable transaction failures")
+			return result, err
+		}
+	}
 
 }
 
-func (s *RetryLayerSystemStore) PermanentDeleteByName(name string) (*model.System, *model.AppError) {
+func (s *RetryLayerSystemStore) PermanentDeleteByName(name string) (*model.System, error) {
 
-	return s.SystemStore.PermanentDeleteByName(name)
+	tries := 0
+	for {
+		result, err := s.SystemStore.PermanentDeleteByName(name)
+		if err == nil {
+			return result, err
+		}
+		if !isRepeatableError(err) {
+			return result, err
+		}
+		tries++
+		if tries >= 3 {
+			err = errors.Wrap(err, "giving up after 3 consecutive repeatable transaction failures")
+			return result, err
+		}
+	}
 
 }
 
-func (s *RetryLayerSystemStore) Save(system *model.System) *model.AppError {
+func (s *RetryLayerSystemStore) Save(system *model.System) error {
 
-	return s.SystemStore.Save(system)
+	tries := 0
+	for {
+		err := s.SystemStore.Save(system)
+		if err == nil {
+			return err
+		}
+		if !isRepeatableError(err) {
+			return err
+		}
+		tries++
+		if tries >= 3 {
+			err = errors.Wrap(err, "giving up after 3 consecutive repeatable transaction failures")
+			return err
+		}
+	}
 
 }
 
-func (s *RetryLayerSystemStore) SaveOrUpdate(system *model.System) *model.AppError {
+func (s *RetryLayerSystemStore) SaveOrUpdate(system *model.System) error {
 
-	return s.SystemStore.SaveOrUpdate(system)
+	tries := 0
+	for {
+		err := s.SystemStore.SaveOrUpdate(system)
+		if err == nil {
+			return err
+		}
+		if !isRepeatableError(err) {
+			return err
+		}
+		tries++
+		if tries >= 3 {
+			err = errors.Wrap(err, "giving up after 3 consecutive repeatable transaction failures")
+			return err
+		}
+	}
 
 }
 
-func (s *RetryLayerSystemStore) Update(system *model.System) *model.AppError {
+func (s *RetryLayerSystemStore) Update(system *model.System) error {
 
-	return s.SystemStore.Update(system)
+	tries := 0
+	for {
+		err := s.SystemStore.Update(system)
+		if err == nil {
+			return err
+		}
+		if !isRepeatableError(err) {
+			return err
+		}
+		tries++
+		if tries >= 3 {
+			err = errors.Wrap(err, "giving up after 3 consecutive repeatable transaction failures")
+			return err
+		}
+	}
 
 }
 
diff --git a/store/sqlstore/system_store.go b/store/sqlstore/system_store.go
index dc4634e0ab..ad756201bb 100644
--- a/store/sqlstore/system_store.go
+++ b/store/sqlstore/system_store.go
@@ -6,10 +6,11 @@ package sqlstore
 import (
 	"context"
 	"database/sql"
-	"net/http"
 
 	"github.com/mattermost/mattermost-server/v5/model"
 	"github.com/mattermost/mattermost-server/v5/store"
+
+	"github.com/pkg/errors"
 )
 
 type SqlSystemStore struct {
@@ -31,38 +32,38 @@ func newSqlSystemStore(sqlStore SqlStore) store.SystemStore {
 func (s SqlSystemStore) createIndexesIfNotExists() {
 }
 
-func (s SqlSystemStore) Save(system *model.System) *model.AppError {
+func (s SqlSystemStore) Save(system *model.System) error {
 	if err := s.GetMaster().Insert(system); err != nil {
-		return model.NewAppError("SqlSystemStore.Save", "store.sql_system.save.app_error", nil, err.Error(), http.StatusInternalServerError)
+		return errors.Wrapf(err, "failed to save system property with name=%s", system.Name)
 	}
 	return nil
 }
 
-func (s SqlSystemStore) SaveOrUpdate(system *model.System) *model.AppError {
+func (s SqlSystemStore) SaveOrUpdate(system *model.System) error {
 	if err := s.GetMaster().SelectOne(&model.System{}, "SELECT * FROM Systems WHERE Name = :Name", map[string]interface{}{"Name": system.Name}); err == nil {
 		if _, err := s.GetMaster().Update(system); err != nil {
-			return model.NewAppError("SqlSystemStore.SaveOrUpdate", "store.sql_system.update.app_error", nil, err.Error(), http.StatusInternalServerError)
+			return errors.Wrapf(err, "failed to update system property with name=%s", system.Name)
 		}
 	} else {
 		if err := s.GetMaster().Insert(system); err != nil {
-			return model.NewAppError("SqlSystemStore.SaveOrUpdate", "store.sql_system.save.app_error", nil, err.Error(), http.StatusInternalServerError)
+			return errors.Wrapf(err, "failed to save system property with name=%s", system.Name)
 		}
 	}
 	return nil
 }
 
-func (s SqlSystemStore) Update(system *model.System) *model.AppError {
+func (s SqlSystemStore) Update(system *model.System) error {
 	if _, err := s.GetMaster().Update(system); err != nil {
-		return model.NewAppError("SqlSystemStore.Update", "store.sql_system.update.app_error", nil, err.Error(), http.StatusInternalServerError)
+		return errors.Wrapf(err, "failed to update system property with name=%s", system.Name)
 	}
 	return nil
 }
 
-func (s SqlSystemStore) Get() (model.StringMap, *model.AppError) {
+func (s SqlSystemStore) Get() (model.StringMap, error) {
 	var systems []model.System
 	props := make(model.StringMap)
 	if _, err := s.GetReplica().Select(&systems, "SELECT * FROM Systems"); err != nil {
-		return nil, model.NewAppError("SqlSystemStore.Get", "store.sql_system.get.app_error", nil, err.Error(), http.StatusInternalServerError)
+		return nil, errors.Wrap(err, "failed to system properties")
 	}
 	for _, prop := range systems {
 		props[prop.Name] = prop.Value
@@ -71,19 +72,19 @@ func (s SqlSystemStore) Get() (model.StringMap, *model.AppError) {
 	return props, nil
 }
 
-func (s SqlSystemStore) GetByName(name string) (*model.System, *model.AppError) {
+func (s SqlSystemStore) GetByName(name string) (*model.System, error) {
 	var system model.System
 	if err := s.GetMaster().SelectOne(&system, "SELECT * FROM Systems WHERE Name = :Name", map[string]interface{}{"Name": name}); err != nil {
-		return nil, model.NewAppError("SqlSystemStore.GetByName", "store.sql_system.get_by_name.app_error", nil, err.Error(), http.StatusInternalServerError)
+		return nil, errors.Wrapf(err, "failed to get system property with name=%s", system.Name)
 	}
 
 	return &system, nil
 }
 
-func (s SqlSystemStore) PermanentDeleteByName(name string) (*model.System, *model.AppError) {
+func (s SqlSystemStore) PermanentDeleteByName(name string) (*model.System, error) {
 	var system model.System
 	if _, err := s.GetMaster().Exec("DELETE FROM Systems WHERE Name = :Name", map[string]interface{}{"Name": name}); err != nil {
-		return nil, model.NewAppError("SqlSystemStore.PermanentDeleteByName", "store.sql_system.permanent_delete_by_name.app_error", nil, err.Error(), http.StatusInternalServerError)
+		return nil, errors.Wrapf(err, "failed to permanent delete system property with name=%s", system.Name)
 	}
 
 	return &system, nil
@@ -91,12 +92,12 @@ func (s SqlSystemStore) PermanentDeleteByName(name string) (*model.System, *mode
 
 // InsertIfExists inserts a given system value if it does not already exist. If a value
 // already exists, it returns the old one, else returns the new one.
-func (s SqlSystemStore) InsertIfExists(system *model.System) (*model.System, *model.AppError) {
+func (s SqlSystemStore) InsertIfExists(system *model.System) (*model.System, error) {
 	tx, err := s.GetMaster().BeginTx(context.Background(), &sql.TxOptions{
 		Isolation: sql.LevelSerializable,
 	})
 	if err != nil {
-		return nil, model.NewAppError("SqlSystemStore.InsertIfExists", "store.sql_system.save.app_error", nil, err.Error(), http.StatusInternalServerError)
+		return nil, errors.Wrap(err, "begin_transaction")
 	}
 	defer finalizeTransaction(tx)
 
@@ -104,7 +105,7 @@ func (s SqlSystemStore) InsertIfExists(system *model.System) (*model.System, *mo
 	if err := tx.SelectOne(&origSystem, `SELECT * FROM Systems
 		WHERE Name = :Name`,
 		map[string]interface{}{"Name": system.Name}); err != nil && err != sql.ErrNoRows {
-		return nil, model.NewAppError("SqlSystemStore.InsertIfExists", "store.sql_system.get_by_name.app_error", nil, err.Error(), http.StatusInternalServerError)
+		return nil, errors.Wrapf(err, "failed to get system property with name=%s", system.Name)
 	}
 
 	if origSystem.Value != "" {
@@ -114,11 +115,11 @@ func (s SqlSystemStore) InsertIfExists(system *model.System) (*model.System, *mo
 
 	// Key does not exist, need to insert.
 	if err := tx.Insert(system); err != nil {
-		return nil, model.NewAppError("SqlSystemStore.InsertIfExists", "store.sql_system.save.app_error", nil, err.Error(), http.StatusInternalServerError)
+		return nil, errors.Wrapf(err, "failed to save system property with name=%s", system.Name)
 	}
 
 	if err := tx.Commit(); err != nil {
-		return nil, model.NewAppError("SqlSystemStore.InsertIfExists", "store.sql_system.save.commit_transaction.app_error", nil, err.Error(), http.StatusInternalServerError)
+		return nil, errors.Wrap(err, "commit_transaction")
 	}
 	return system, nil
 }
diff --git a/store/store.go b/store/store.go
index ae84c97d8d..302039595f 100644
--- a/store/store.go
+++ b/store/store.go
@@ -429,13 +429,13 @@ type OAuthStore interface {
 }
 
 type SystemStore interface {
-	Save(system *model.System) *model.AppError
-	SaveOrUpdate(system *model.System) *model.AppError
-	Update(system *model.System) *model.AppError
-	Get() (model.StringMap, *model.AppError)
-	GetByName(name string) (*model.System, *model.AppError)
-	PermanentDeleteByName(name string) (*model.System, *model.AppError)
-	InsertIfExists(system *model.System) (*model.System, *model.AppError)
+	Save(system *model.System) error
+	SaveOrUpdate(system *model.System) error
+	Update(system *model.System) error
+	Get() (model.StringMap, error)
+	GetByName(name string) (*model.System, error)
+	PermanentDeleteByName(name string) (*model.System, error)
+	InsertIfExists(system *model.System) (*model.System, error)
 }
 
 type WebhookStore interface {
diff --git a/store/storetest/mocks/SystemStore.go b/store/storetest/mocks/SystemStore.go
index 048182861b..5c7b5cb6e9 100644
--- a/store/storetest/mocks/SystemStore.go
+++ b/store/storetest/mocks/SystemStore.go
@@ -15,7 +15,7 @@ type SystemStore struct {
 }
 
 // Get provides a mock function with given fields:
-func (_m *SystemStore) Get() (model.StringMap, *model.AppError) {
+func (_m *SystemStore) Get() (model.StringMap, error) {
 	ret := _m.Called()
 
 	var r0 model.StringMap
@@ -27,20 +27,18 @@ func (_m *SystemStore) Get() (model.StringMap, *model.AppError) {
 		}
 	}
 
-	var r1 *model.AppError
-	if rf, ok := ret.Get(1).(func() *model.AppError); ok {
+	var r1 error
+	if rf, ok := ret.Get(1).(func() error); ok {
 		r1 = rf()
 	} else {
-		if ret.Get(1) != nil {
-			r1 = ret.Get(1).(*model.AppError)
-		}
+		r1 = ret.Error(1)
 	}
 
 	return r0, r1
 }
 
 // GetByName provides a mock function with given fields: name
-func (_m *SystemStore) GetByName(name string) (*model.System, *model.AppError) {
+func (_m *SystemStore) GetByName(name string) (*model.System, error) {
 	ret := _m.Called(name)
 
 	var r0 *model.System
@@ -52,20 +50,18 @@ func (_m *SystemStore) GetByName(name string) (*model.System, *model.AppError) {
 		}
 	}
 
-	var r1 *model.AppError
-	if rf, ok := ret.Get(1).(func(string) *model.AppError); ok {
+	var r1 error
+	if rf, ok := ret.Get(1).(func(string) error); ok {
 		r1 = rf(name)
 	} else {
-		if ret.Get(1) != nil {
-			r1 = ret.Get(1).(*model.AppError)
-		}
+		r1 = ret.Error(1)
 	}
 
 	return r0, r1
 }
 
 // InsertIfExists provides a mock function with given fields: system
-func (_m *SystemStore) InsertIfExists(system *model.System) (*model.System, *model.AppError) {
+func (_m *SystemStore) InsertIfExists(system *model.System) (*model.System, error) {
 	ret := _m.Called(system)
 
 	var r0 *model.System
@@ -77,20 +73,18 @@ func (_m *SystemStore) InsertIfExists(system *model.System) (*model.System, *mod
 		}
 	}
 
-	var r1 *model.AppError
-	if rf, ok := ret.Get(1).(func(*model.System) *model.AppError); ok {
+	var r1 error
+	if rf, ok := ret.Get(1).(func(*model.System) error); ok {
 		r1 = rf(system)
 	} else {
-		if ret.Get(1) != nil {
-			r1 = ret.Get(1).(*model.AppError)
-		}
+		r1 = ret.Error(1)
 	}
 
 	return r0, r1
 }
 
 // PermanentDeleteByName provides a mock function with given fields: name
-func (_m *SystemStore) PermanentDeleteByName(name string) (*model.System, *model.AppError) {
+func (_m *SystemStore) PermanentDeleteByName(name string) (*model.System, error) {
 	ret := _m.Called(name)
 
 	var r0 *model.System
@@ -102,61 +96,53 @@ func (_m *SystemStore) PermanentDeleteByName(name string) (*model.System, *model
 		}
 	}
 
-	var r1 *model.AppError
-	if rf, ok := ret.Get(1).(func(string) *model.AppError); ok {
+	var r1 error
+	if rf, ok := ret.Get(1).(func(string) error); ok {
 		r1 = rf(name)
 	} else {
-		if ret.Get(1) != nil {
-			r1 = ret.Get(1).(*model.AppError)
-		}
+		r1 = ret.Error(1)
 	}
 
 	return r0, r1
 }
 
 // Save provides a mock function with given fields: system
-func (_m *SystemStore) Save(system *model.System) *model.AppError {
+func (_m *SystemStore) Save(system *model.System) error {
 	ret := _m.Called(system)
 
-	var r0 *model.AppError
-	if rf, ok := ret.Get(0).(func(*model.System) *model.AppError); ok {
+	var r0 error
+	if rf, ok := ret.Get(0).(func(*model.System) error); ok {
 		r0 = rf(system)
 	} else {
-		if ret.Get(0) != nil {
-			r0 = ret.Get(0).(*model.AppError)
-		}
+		r0 = ret.Error(0)
 	}
 
 	return r0
 }
 
 // SaveOrUpdate provides a mock function with given fields: system
-func (_m *SystemStore) SaveOrUpdate(system *model.System) *model.AppError {
+func (_m *SystemStore) SaveOrUpdate(system *model.System) error {
 	ret := _m.Called(system)
 
-	var r0 *model.AppError
-	if rf, ok := ret.Get(0).(func(*model.System) *model.AppError); ok {
+	var r0 error
+	if rf, ok := ret.Get(0).(func(*model.System) error); ok {
 		r0 = rf(system)
 	} else {
-		if ret.Get(0) != nil {
-			r0 = ret.Get(0).(*model.AppError)
-		}
+		r0 = ret.Error(0)
 	}
 
 	return r0
 }
 
 // Update provides a mock function with given fields: system
-func (_m *SystemStore) Update(system *model.System) *model.AppError {
+func (_m *SystemStore) Update(system *model.System) error {
 	ret := _m.Called(system)
 
-	var r0 *model.AppError
-	if rf, ok := ret.Get(0).(func(*model.System) *model.AppError); ok {
+	var r0 error
+	if rf, ok := ret.Get(0).(func(*model.System) error); ok {
 		r0 = rf(system)
 	} else {
-		if ret.Get(0) != nil {
-			r0 = ret.Get(0).(*model.AppError)
-		}
+		r0 = ret.Error(0)
 	}
 
 	return r0
diff --git a/store/storetest/system_store.go b/store/storetest/system_store.go
index bb034c3cd8..2e51c66b8a 100644
--- a/store/storetest/system_store.go
+++ b/store/storetest/system_store.go
@@ -111,7 +111,7 @@ func testInsertIfExists(t *testing.T, ss store.Store) {
 		go func() {
 			defer wg.Done()
 			s1 := &model.System{Name: model.SYSTEM_CLUSTER_ENCRYPTION_KEY, Value: "firstKey"}
-			var err *model.AppError
+			var err error
 			s2, err = ss.System().InsertIfExists(s1)
 			require.Nil(t, err)
 		}()
@@ -119,7 +119,7 @@ func testInsertIfExists(t *testing.T, ss store.Store) {
 		go func() {
 			defer wg.Done()
 			s1 := &model.System{Name: model.SYSTEM_CLUSTER_ENCRYPTION_KEY, Value: "secondKey"}
-			var err *model.AppError
+			var err error
 			s3, err = ss.System().InsertIfExists(s1)
 			require.Nil(t, err)
 		}()
diff --git a/store/timerlayer/timerlayer.go b/store/timerlayer/timerlayer.go
index e6e5c31aea..8f56094be1 100644
--- a/store/timerlayer/timerlayer.go
+++ b/store/timerlayer/timerlayer.go
@@ -5724,7 +5724,7 @@ func (s *TimerLayerStatusStore) UpdateLastActivityAt(userId string, lastActivity
 	return err
 }
 
-func (s *TimerLayerSystemStore) Get() (model.StringMap, *model.AppError) {
+func (s *TimerLayerSystemStore) Get() (model.StringMap, error) {
 	start := timemodule.Now()
 
 	result, err := s.SystemStore.Get()
@@ -5740,7 +5740,7 @@ func (s *TimerLayerSystemStore) Get() (model.StringMap, *model.AppError) {
 	return result, err
 }
 
-func (s *TimerLayerSystemStore) GetByName(name string) (*model.System, *model.AppError) {
+func (s *TimerLayerSystemStore) GetByName(name string) (*model.System, error) {
 	start := timemodule.Now()
 
 	result, err := s.SystemStore.GetByName(name)
@@ -5756,7 +5756,7 @@ func (s *TimerLayerSystemStore) GetByName(name string) (*model.System, *model.Ap
 	return result, err
 }
 
-func (s *TimerLayerSystemStore) InsertIfExists(system *model.System) (*model.System, *model.AppError) {
+func (s *TimerLayerSystemStore) InsertIfExists(system *model.System) (*model.System, error) {
 	start := timemodule.Now()
 
 	result, err := s.SystemStore.InsertIfExists(system)
@@ -5772,7 +5772,7 @@ func (s *TimerLayerSystemStore) InsertIfExists(system *model.System) (*model.Sys
 	return result, err
 }
 
-func (s *TimerLayerSystemStore) PermanentDeleteByName(name string) (*model.System, *model.AppError) {
+func (s *TimerLayerSystemStore) PermanentDeleteByName(name string) (*model.System, error) {
 	start := timemodule.Now()
 
 	result, err := s.SystemStore.PermanentDeleteByName(name)
@@ -5788,7 +5788,7 @@ func (s *TimerLayerSystemStore) PermanentDeleteByName(name string) (*model.Syste
 	return result, err
 }
 
-func (s *TimerLayerSystemStore) Save(system *model.System) *model.AppError {
+func (s *TimerLayerSystemStore) Save(system *model.System) error {
 	start := timemodule.Now()
 
 	err := s.SystemStore.Save(system)
@@ -5804,7 +5804,7 @@ func (s *TimerLayerSystemStore) Save(system *model.System) *model.AppError {
 	return err
 }
 
-func (s *TimerLayerSystemStore) SaveOrUpdate(system *model.System) *model.AppError {
+func (s *TimerLayerSystemStore) SaveOrUpdate(system *model.System) error {
 	start := timemodule.Now()
 
 	err := s.SystemStore.SaveOrUpdate(system)
@@ -5820,7 +5820,7 @@ func (s *TimerLayerSystemStore) SaveOrUpdate(system *model.System) *model.AppErr
 	return err
 }
 
-func (s *TimerLayerSystemStore) Update(system *model.System) *model.AppError {
+func (s *TimerLayerSystemStore) Update(system *model.System) error {
 	start := timemodule.Now()
 
 	err := s.SystemStore.Update(system)
diff --git a/testlib/store.go b/testlib/store.go
index 94a6bfa4fb..3702502703 100644
--- a/testlib/store.go
+++ b/testlib/store.go
@@ -24,8 +24,8 @@ func (s *TestStore) Close() {
 func GetMockStoreForSetupFunctions() *mocks.Store {
 	mockStore := mocks.Store{}
 	systemStore := mocks.SystemStore{}
-	systemStore.On("GetByName", "AsymmetricSigningKey").Return(nil, model.NewAppError("FakeError", "store.sql_system.get_by_name.app_error", nil, "", http.StatusInternalServerError))
-	systemStore.On("GetByName", "PostActionCookieSecret").Return(nil, model.NewAppError("FakeError", "store.sql_system.get_by_name.app_error", nil, "", http.StatusInternalServerError))
+	systemStore.On("GetByName", "AsymmetricSigningKey").Return(nil, model.NewAppError("FakeError", "app.system.get_by_name.app_error", nil, "", http.StatusInternalServerError))
+	systemStore.On("GetByName", "PostActionCookieSecret").Return(nil, model.NewAppError("FakeError", "app.system.get_by_name.app_error", nil, "", http.StatusInternalServerError))
 	systemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: strconv.FormatInt(model.GetMillis(), 10)}, nil)
 	systemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
 	systemStore.On("GetByName", "AdvancedPermissionsMigrationComplete").Return(&model.System{Name: "AdvancedPermissionsMigrationComplete", Value: "true"}, nil)