[MM-44489] Cloud limits: enforcing files (#20703)

* Update last accessible file time

* Filter fileInfos

* Set inaccessible header

* Fix lint issue

* Fix lint issue

* Fix i18n

* add nil check

* Fix merge conflicts

* Add helper functions to clear out inaccessible files content

* Remove content for inaccessible files

* Fix typo

* wip

* Remove InaccessibleContent field, instead use Archived

* Add store tests

* Add tests

* Add separate funcs to ignore cloud limits

* Use separate query for MySql

* Use GetReplicaX

Co-authored-by: Mattermod <mattermod@users.noreply.github.com>

api4/file.go

@@ -482,6 +482,7 @@ func getFile(c *Context, w http.ResponseWriter, r *http.Request) {
 	info, err := c.App.GetFileInfo(c.Params.FileId)
 	if err != nil {
 		c.Err = err
+		setInaccessibleFileHeader(w, err)
 		return
 	}
 	auditRec.AddMeta("file", info)
@@ -514,6 +515,7 @@ func getFileThumbnail(c *Context, w http.ResponseWriter, r *http.Request) {
 	info, err := c.App.GetFileInfo(c.Params.FileId)
 	if err != nil {
 		c.Err = err
+		setInaccessibleFileHeader(w, err)
 		return
 	}
 
@@ -555,6 +557,7 @@ func getFileLink(c *Context, w http.ResponseWriter, r *http.Request) {
 	info, err := c.App.GetFileInfo(c.Params.FileId)
 	if err != nil {
 		c.Err = err
+		setInaccessibleFileHeader(w, err)
 		return
 	}
 	auditRec.AddMeta("file", info)
@@ -589,6 +592,7 @@ func getFilePreview(c *Context, w http.ResponseWriter, r *http.Request) {
 	info, err := c.App.GetFileInfo(c.Params.FileId)
 	if err != nil {
 		c.Err = err
+		setInaccessibleFileHeader(w, err)
 		return
 	}
 
@@ -622,6 +626,7 @@ func getFileInfo(c *Context, w http.ResponseWriter, r *http.Request) {
 	info, err := c.App.GetFileInfo(c.Params.FileId)
 	if err != nil {
 		c.Err = err
+		setInaccessibleFileHeader(w, err)
 		return
 	}
 
@@ -650,6 +655,7 @@ func getPublicFile(c *Context, w http.ResponseWriter, r *http.Request) {
 	info, err := c.App.GetFileInfo(c.Params.FileId)
 	if err != nil {
 		c.Err = err
+		setInaccessibleFileHeader(w, err)
 		return
 	}
 
@@ -824,3 +830,10 @@ func searchFiles(c *Context, w http.ResponseWriter, r *http.Request, teamID stri
 		c.Logger.Warn("Error while writing response", mlog.Err(err))
 	}
 }
+
+func setInaccessibleFileHeader(w http.ResponseWriter, appErr *model.AppError) {
+	// File is inaccessible due to cloud plan's limit.
+	if appErr.Id == "app.file.cloud.get.app_error" {
+		w.Header().Set(model.HeaderFirstInaccessibleFileTime, "1")
+	}
+}

app/app_iface.go

@@ -76,6 +76,9 @@ type AppIface interface {
 	CheckProviderAttributes(user *model.User, patch *model.UserPatch) string
 	// ClientConfigWithComputed gets the configuration in a format suitable for sending to the client.
 	ClientConfigWithComputed() map[string]string
+	// ComputeLastAccessibleFileTime updates cache with CreateAt time of the last accessible file as per the cloud plan's limit.
+	// Use GetLastAccessibleFileTime() to access the result.
+	ComputeLastAccessibleFileTime() error
 	// ComputeLastAccessiblePostTime updates cache with CreateAt time of the last accessible post as per the cloud plan's limit.
 	// Use GetLastAccessiblePostTime() to access the result.
 	ComputeLastAccessiblePostTime() error
@@ -176,6 +179,8 @@ type AppIface interface {
 	// GetEnvironmentConfig returns a map of configuration keys whose values have been overridden by an environment variable.
 	// If filter is not nil and returns false for a struct field, that field will be omitted.
 	GetEnvironmentConfig(filter func(reflect.StructField) bool) map[string]any
+	// GetFileInfosForPost also returns firstInaccessibleFileTime based on cloud plan's limit.
+	GetFileInfosForPost(postID string, fromMaster bool, includeDeleted bool) ([]*model.FileInfo, int64, *model.AppError)
 	// GetFilteredUsersStats is used to get a count of users based on the set of filters supported by UserCountOptions.
 	GetFilteredUsersStats(options *model.UserCountOptions) (*model.UsersStats, *model.AppError)
 	// GetGroupsByTeam returns the paged list and the total count of group associated to the given team.
@@ -186,6 +191,8 @@ type AppIface interface {
 	// relationship with a user. That means any user sharing any channel, including
 	// direct and group channels.
 	GetKnownUsers(userID string) ([]string, *model.AppError)
+	// GetLastAccessibleFileTime returns CreateAt time(from cache) of the last accessible post as per the cloud limit
+	GetLastAccessibleFileTime() (int64, *model.AppError)
 	// GetLastAccessiblePostTime returns CreateAt time(from cache) of the last accessible post as per the cloud limit
 	GetLastAccessiblePostTime() (int64, *model.AppError)
 	// GetLdapGroup retrieves a single LDAP group by the given LDAP group id.
@@ -634,7 +641,6 @@ type AppIface interface {
 	GetFile(fileID string) ([]byte, *model.AppError)
 	GetFileInfo(fileID string) (*model.FileInfo, *model.AppError)
 	GetFileInfos(page, perPage int, opt *model.GetFileInfosOptions) ([]*model.FileInfo, *model.AppError)
-	GetFileInfosForPost(postID string, fromMaster bool, includeDeleted bool) ([]*model.FileInfo, *model.AppError)
 	GetFileInfosForPostWithMigration(postID string, includeDeleted bool) ([]*model.FileInfo, *model.AppError)
 	GetFlaggedPosts(userID string, offset int, limit int) (*model.PostList, *model.AppError)
 	GetFlaggedPostsForChannel(userID, channelID string, offset int, limit int) (*model.PostList, *model.AppError)

app/file.go

@@ -12,12 +12,14 @@ import (
 	"fmt"
 	"image"
 	"io"
+	"math"
 	"net/http"
 	"net/url"
 	"os"
 	"path"
 	"path/filepath"
 	"regexp"
+	"strconv"
 	"strings"
 	"sync"
 	"time"
@@ -1082,11 +1084,30 @@ func (s *Server) getFileInfo(fileID string) (*model.FileInfo, *model.AppError) {
 }
 
 func (a *App) GetFileInfo(fileID string) (*model.FileInfo, *model.AppError) {
-	fileInfo, err := a.Srv().getFileInfo(fileID)
-	if err == nil {
+	fileInfo, appErr := a.Srv().getFileInfo(fileID)
+	if appErr != nil {
+		return nil, appErr
+	}
+
+	firstInaccessibleFileTime, appErr := a.isInaccessibleFile(fileInfo)
+	if appErr != nil {
+		return nil, appErr
+	}
+	if firstInaccessibleFileTime > 0 {
+		return nil, model.NewAppError("GetFileInfo", "app.file.cloud.get.app_error", nil, "", http.StatusForbidden)
+	}
+
+	a.generateMiniPreview(fileInfo)
+	return fileInfo, appErr
+}
+
+func (a *App) getFileInfoIgnoreCloudLimit(fileID string) (*model.FileInfo, *model.AppError) {
+	fileInfo, appErr := a.Srv().getFileInfo(fileID)
+	if appErr == nil {
 		a.generateMiniPreview(fileInfo)
 	}
-	return fileInfo, err
+
+	return fileInfo, appErr
 }
 
 func (a *App) GetFileInfos(page, perPage int, opt *model.GetFileInfosOptions) ([]*model.FileInfo, *model.AppError) {
@@ -1104,6 +1125,16 @@ func (a *App) GetFileInfos(page, perPage int, opt *model.GetFileInfosOptions) ([
 		}
 	}
 
+	filterOptions := filterFileOptions{}
+	if opt != nil && (opt.SortBy == "" || opt.SortBy == model.FileinfoSortByCreated) {
+		filterOptions.assumeSortedCreatedAt = true
+	}
+
+	fileInfos, _, appErr := a.getFilteredAccessibleFiles(fileInfos, filterOptions)
+	if appErr != nil {
+		return nil, appErr
+	}
+
 	a.generateMiniPreviewForInfos(fileInfos)
 
 	return fileInfos, nil
@@ -1123,6 +1154,20 @@ func (a *App) GetFile(fileID string) ([]byte, *model.AppError) {
 	return data, nil
 }
 
+func (a *App) getFileIgnoreCloudLimit(fileID string) ([]byte, *model.AppError) {
+	info, err := a.getFileInfoIgnoreCloudLimit(fileID)
+	if err != nil {
+		return nil, err
+	}
+
+	data, err := a.ReadFile(info.Path)
+	if err != nil {
+		return nil, err
+	}
+
+	return data, nil
+}
+
 func (a *App) CopyFileInfos(userID string, fileIDs []string) ([]string, *model.AppError) {
 	var newFileIds []string
 
@@ -1252,7 +1297,7 @@ func (a *App) SearchFilesInTeamForUser(c *request.Context, terms string, userId
 		}
 	}
 
-	return fileInfoSearchResults, nil
+	return fileInfoSearchResults, a.filterInaccessibleFiles(fileInfoSearchResults, filterFileOptions{assumeSortedCreatedAt: true})
 }
 
 func (a *App) ExtractContentFromFileInfo(fileInfo *model.FileInfo) error {
@@ -1288,3 +1333,79 @@ func (a *App) ExtractContentFromFileInfo(fileInfo *model.FileInfo) error {
 	}
 	return nil
 }
+
+// GetLastAccessibleFileTime returns CreateAt time(from cache) of the last accessible post as per the cloud limit
+func (a *App) GetLastAccessibleFileTime() (int64, *model.AppError) {
+	license := a.Srv().License()
+	if license == nil || !*license.Features.Cloud {
+		return 0, nil
+	}
+
+	system, err := a.Srv().Store.System().GetByName(model.SystemLastAccessibleFileTime)
+	if err != nil {
+		var nfErr *store.ErrNotFound
+		switch {
+		case errors.As(err, &nfErr):
+			// All files are accessible
+			return 0, nil
+		default:
+			return 0, model.NewAppError("GetLastAccessibleFileTime", "app.system.get_by_name.app_error", nil, err.Error(), http.StatusInternalServerError)
+		}
+	}
+
+	lastAccessibleFileTime, err := strconv.ParseInt(system.Value, 10, 64)
+	if err != nil {
+		return 0, model.NewAppError("GetLastAccessibleFileTime", "common.parse_error_int64", map[string]interface{}{"Value": system.Value}, err.Error(), http.StatusInternalServerError)
+	}
+
+	return lastAccessibleFileTime, nil
+}
+
+// ComputeLastAccessibleFileTime updates cache with CreateAt time of the last accessible file as per the cloud plan's limit.
+// Use GetLastAccessibleFileTime() to access the result.
+func (a *App) ComputeLastAccessibleFileTime() error {
+	limit, appErr := a.getCloudFilesSizeLimit()
+	if appErr != nil {
+		return appErr
+	}
+
+	createdAt, err := a.Srv().GetStore().FileInfo().GetUptoNSizeFileTime(limit)
+	if err != nil {
+		var nfErr *store.ErrNotFound
+		if !errors.As(err, &nfErr) {
+			return model.NewAppError("ComputeLastAccessibleFileTime", "app.last_accessible_file.app_error", nil, err.Error(), http.StatusInternalServerError)
+		}
+	}
+
+	// Update Cache
+	err = a.Srv().Store.System().SaveOrUpdate(&model.System{
+		Name:  model.SystemLastAccessibleFileTime,
+		Value: strconv.FormatInt(createdAt, 10),
+	})
+	if err != nil {
+		return model.NewAppError("ComputeLastAccessibleFileTime", "app.system.save.app_error", nil, err.Error(), http.StatusInternalServerError)
+	}
+
+	return nil
+}
+
+// getCloudFilesSizeLimit returns size in bytes
+func (a *App) getCloudFilesSizeLimit() (int64, *model.AppError) {
+	license := a.Srv().License()
+	if license == nil || !*license.Features.Cloud {
+		return 0, nil
+	}
+
+	// limits is in bits
+	limits, err := a.Cloud().GetCloudLimits("")
+	if err != nil {
+		return 0, model.NewAppError("getCloudFilesSizeLimit", "api.cloud.app_error", nil, err.Error(), http.StatusInternalServerError)
+	}
+
+	if limits == nil || limits.Files == nil || limits.Files.TotalStorage == nil {
+		// Cloud limit is not applicable
+		return 0, nil
+	}
+
+	return int64(math.Ceil(float64(*limits.Files.TotalStorage) / 8)), nil
+}

app/file_helper.go

@@ -0,0 +1,210 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+package app
+
+import (
+	"net/http"
+
+	"github.com/mattermost/mattermost-server/v6/model"
+)
+
+// removeInaccessibleContentFromFilesSlice removes content from the files beyond the cloud plan's limit
+// and also returns the firstInaccessibleFileTime
+func (a *App) removeInaccessibleContentFromFilesSlice(files []*model.FileInfo) (int64, *model.AppError) {
+	if len(files) == 0 {
+		return 0, nil
+	}
+
+	lastAccessibleFileTime, appErr := a.GetLastAccessibleFileTime()
+	if appErr != nil {
+		return 0, model.NewAppError("removeInaccessibleFileListContent", "app.last_accessible_file.app_error", nil, appErr.Error(), http.StatusInternalServerError)
+	}
+	if lastAccessibleFileTime == 0 {
+		// No need to remove content, all files are accessible
+		return 0, nil
+	}
+
+	var firstInaccessibleFileTime int64 = 0
+	for _, file := range files {
+		if createAt := file.CreateAt; createAt < lastAccessibleFileTime {
+			file.MakeContentInaccessible()
+			if createAt > firstInaccessibleFileTime {
+				firstInaccessibleFileTime = createAt
+			}
+		}
+	}
+
+	return firstInaccessibleFileTime, nil
+}
+
+// filterInaccessibleFiles filters out the files, past the cloud limit
+func (a *App) filterInaccessibleFiles(fileList *model.FileInfoList, options filterFileOptions) *model.AppError {
+	if fileList == nil || fileList.FileInfos == nil || len(fileList.FileInfos) == 0 {
+		return nil
+	}
+
+	lastAccessibleFileTime, appErr := a.GetLastAccessibleFileTime()
+	if appErr != nil {
+		return model.NewAppError("filterInaccessibleFiles", "app.last_accessible_file.app_error", nil, appErr.Error(), http.StatusInternalServerError)
+	}
+	if lastAccessibleFileTime == 0 {
+		// No need to filter, all files are accessible
+		return nil
+	}
+
+	if len(fileList.FileInfos) == len(fileList.Order) && options.assumeSortedCreatedAt {
+		lenFiles := len(fileList.FileInfos)
+		getCreateAt := func(i int) int64 { return fileList.FileInfos[fileList.Order[i]].CreateAt }
+
+		bounds := getTimeSortedPostAccessibleBounds(lastAccessibleFileTime, lenFiles, getCreateAt)
+
+		if bounds.allAccessible(lenFiles) {
+			return nil
+		}
+		if bounds.noAccessible() {
+			if lenFiles > 0 {
+				firstFileCreatedAt := fileList.FileInfos[fileList.Order[0]].CreateAt
+				lastFileCreatedAt := fileList.FileInfos[fileList.Order[lenFiles-1]].CreateAt
+				fileList.FirstInaccessibleFileTime = max(firstFileCreatedAt, lastFileCreatedAt)
+			}
+			fileList.FileInfos = map[string]*model.FileInfo{}
+			fileList.Order = []string{}
+			return nil
+		}
+		startInaccessibleIndex, endInaccessibleIndex := bounds.getInaccessibleRange(len(fileList.Order))
+		startInaccessibleCreatedAt := fileList.FileInfos[fileList.Order[startInaccessibleIndex]].CreateAt
+		endInaccessibleCreatedAt := fileList.FileInfos[fileList.Order[endInaccessibleIndex]].CreateAt
+		fileList.FirstInaccessibleFileTime = max(startInaccessibleCreatedAt, endInaccessibleCreatedAt)
+
+		files := fileList.FileInfos
+		order := fileList.Order
+		accessibleCount := bounds.end - bounds.start + 1
+		inaccessibleCount := lenFiles - accessibleCount
+		// Linearly cover shorter route to traverse files map
+		if inaccessibleCount < accessibleCount {
+			for i := 0; i < bounds.start; i++ {
+				delete(files, order[i])
+			}
+			for i := bounds.end + 1; i < lenFiles; i++ {
+				delete(files, order[i])
+			}
+		} else {
+			accessibleFiles := make(map[string]*model.FileInfo, accessibleCount)
+			for i := bounds.start; i <= bounds.end; i++ {
+				accessibleFiles[order[i]] = files[order[i]]
+			}
+			fileList.FileInfos = accessibleFiles
+		}
+
+		fileList.Order = fileList.Order[bounds.start : bounds.end+1]
+	} else {
+		linearFilterFileList(fileList, lastAccessibleFileTime)
+	}
+
+	return nil
+}
+
+// isInaccessibleFile indicates if the file is past the cloud plan's limit.
+func (a *App) isInaccessibleFile(file *model.FileInfo) (int64, *model.AppError) {
+	if file == nil {
+		return 0, nil
+	}
+
+	fl := &model.FileInfoList{
+		Order:     []string{file.Id},
+		FileInfos: map[string]*model.FileInfo{file.Id: file},
+	}
+
+	appErr := a.filterInaccessibleFiles(fl, filterFileOptions{assumeSortedCreatedAt: true})
+	return fl.FirstInaccessibleFileTime, appErr
+}
+
+// getFilteredAccessibleFiles returns accessible files filtered as per the cloud plan's limit and also indicates if there were any inaccessible files
+func (a *App) getFilteredAccessibleFiles(files []*model.FileInfo, options filterFileOptions) ([]*model.FileInfo, int64, *model.AppError) {
+	if len(files) == 0 {
+		return files, 0, nil
+	}
+
+	filteredFiles := []*model.FileInfo{}
+	lastAccessibleFileTime, appErr := a.GetLastAccessibleFileTime()
+	if appErr != nil {
+		return filteredFiles, 0, model.NewAppError("getFilteredAccessibleFiles", "app.last_accessible_file.app_error", nil, appErr.Error(), http.StatusInternalServerError)
+	} else if lastAccessibleFileTime == 0 {
+		// No need to filter, all files are accessible
+		return files, 0, nil
+	}
+
+	if options.assumeSortedCreatedAt {
+		lenFiles := len(files)
+		getCreateAt := func(i int) int64 { return files[i].CreateAt }
+		bounds := getTimeSortedPostAccessibleBounds(lastAccessibleFileTime, lenFiles, getCreateAt)
+		if bounds.allAccessible(lenFiles) {
+			return files, 0, nil
+		}
+		if bounds.noAccessible() {
+			var firstInaccessibleFileTime int64 = 0
+			if lenFiles > 0 {
+				firstFileCreatedAt := files[0].CreateAt
+				lastFileCreatedAt := files[len(files)-1].CreateAt
+				firstInaccessibleFileTime = max(firstFileCreatedAt, lastFileCreatedAt)
+			}
+			return filteredFiles, firstInaccessibleFileTime, nil
+		}
+
+		startInaccessibleIndex, endInaccessibleIndex := bounds.getInaccessibleRange(len(files))
+		firstFileCreatedAt := files[startInaccessibleIndex].CreateAt
+		lastFileCreatedAt := files[endInaccessibleIndex].CreateAt
+		firstInaccessibleFileTime := max(firstFileCreatedAt, lastFileCreatedAt)
+		filteredFiles = files[bounds.start : bounds.end+1]
+		return filteredFiles, firstInaccessibleFileTime, nil
+	}
+
+	filteredFiles, firstInaccessibleFileTime := linearFilterFilesSlice(files, lastAccessibleFileTime)
+	return filteredFiles, firstInaccessibleFileTime, nil
+}
+
+type filterFileOptions struct {
+	assumeSortedCreatedAt bool
+}
+
+// linearFilterFileList make no assumptions about ordering, go through files one by one
+// this is the slower fallback that is still safe
+// if we can not assume files are ordered by CreatedAt
+func linearFilterFileList(fileList *model.FileInfoList, earliestAccessibleTime int64) {
+	files := fileList.FileInfos
+	order := fileList.Order
+
+	n := 0
+	for i, fileID := range order {
+		if createAt := files[fileID].CreateAt; createAt >= earliestAccessibleTime {
+			order[n] = order[i]
+			n++
+		} else {
+			if createAt > fileList.FirstInaccessibleFileTime {
+				fileList.FirstInaccessibleFileTime = createAt
+			}
+			delete(files, fileID)
+		}
+	}
+	fileList.Order = order[:n]
+}
+
+// linearFilterFilesSlice make no assumptions about ordering, go through files one by one
+// this is the slower fallback that is still safe
+// if we can not assume files are ordered by CreatedAt
+func linearFilterFilesSlice(files []*model.FileInfo, earliestAccessibleTime int64) ([]*model.FileInfo, int64) {
+	var firstInaccessibleFileTime int64 = 0
+	n := 0
+	for i := range files {
+		if createAt := files[i].CreateAt; createAt >= earliestAccessibleTime {
+			files[n] = files[i]
+			n++
+		} else {
+			if createAt > firstInaccessibleFileTime {
+				firstInaccessibleFileTime = createAt
+			}
+		}
+	}
+	return files[:n], firstInaccessibleFileTime
+}

app/file_helper_test.go

@@ -0,0 +1,206 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+package app
+
+import (
+	"testing"
+
+	"github.com/mattermost/mattermost-server/v6/model"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestFilterInaccessibleFiles(t *testing.T) {
+	th := Setup(t)
+	th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
+	th.App.Srv().Store.System().Save(&model.System{
+		Name:  model.SystemLastAccessibleFileTime,
+		Value: "2",
+	})
+
+	defer th.TearDown()
+
+	var getFileWithCreateAt = func(at int64) *model.FileInfo {
+		return &model.FileInfo{CreateAt: at}
+	}
+
+	t.Run("ascending order returns correct files", func(t *testing.T) {
+		fileList := &model.FileInfoList{
+			FileInfos: map[string]*model.FileInfo{
+				"file_a": getFileWithCreateAt(0),
+				"file_b": getFileWithCreateAt(1),
+				"file_c": getFileWithCreateAt(2),
+				"file_d": getFileWithCreateAt(3),
+				"file_e": getFileWithCreateAt(4),
+			},
+			Order: []string{"file_a", "file_b", "file_c", "file_d", "file_e"},
+		}
+		appErr := th.App.filterInaccessibleFiles(fileList, filterFileOptions{assumeSortedCreatedAt: true})
+
+		require.Nil(t, appErr)
+
+		assert.Equal(t, map[string]*model.FileInfo{
+			"file_c": getFileWithCreateAt(2),
+			"file_d": getFileWithCreateAt(3),
+			"file_e": getFileWithCreateAt(4),
+		}, fileList.FileInfos)
+
+		assert.Equal(t, []string{
+			"file_c",
+			"file_d",
+			"file_e",
+		}, fileList.Order)
+		assert.Equal(t, int64(1), fileList.FirstInaccessibleFileTime)
+	})
+
+	t.Run("descending order returns correct files", func(t *testing.T) {
+		fileList := &model.FileInfoList{
+			FileInfos: map[string]*model.FileInfo{
+				"file_a": getFileWithCreateAt(0),
+				"file_b": getFileWithCreateAt(1),
+				"file_c": getFileWithCreateAt(2),
+				"file_d": getFileWithCreateAt(3),
+				"file_e": getFileWithCreateAt(4),
+			},
+			Order: []string{"file_e", "file_d", "file_c", "file_b", "file_a"},
+		}
+		appErr := th.App.filterInaccessibleFiles(fileList, filterFileOptions{assumeSortedCreatedAt: true})
+
+		require.Nil(t, appErr)
+
+		assert.Equal(t, map[string]*model.FileInfo{
+			"file_c": getFileWithCreateAt(2),
+			"file_d": getFileWithCreateAt(3),
+			"file_e": getFileWithCreateAt(4),
+		}, fileList.FileInfos)
+
+		assert.Equal(t, []string{
+			"file_e",
+			"file_d",
+			"file_c",
+		}, fileList.Order)
+
+		assert.Equal(t, int64(1), fileList.FirstInaccessibleFileTime)
+	})
+
+	t.Run("handles mixed create at ordering correctly if correct options given", func(t *testing.T) {
+		fileList := &model.FileInfoList{
+			FileInfos: map[string]*model.FileInfo{
+				"file_a": getFileWithCreateAt(0),
+				"file_b": getFileWithCreateAt(1),
+				"file_c": getFileWithCreateAt(2),
+				"file_d": getFileWithCreateAt(3),
+				"file_e": getFileWithCreateAt(4),
+			},
+			Order: []string{"file_e", "file_b", "file_a", "file_d", "file_c"},
+		}
+		appErr := th.App.filterInaccessibleFiles(fileList, filterFileOptions{assumeSortedCreatedAt: false})
+
+		require.Nil(t, appErr)
+
+		assert.Equal(t, map[string]*model.FileInfo{
+			"file_c": getFileWithCreateAt(2),
+			"file_d": getFileWithCreateAt(3),
+			"file_e": getFileWithCreateAt(4),
+		}, fileList.FileInfos)
+
+		assert.Equal(t, []string{
+			"file_e",
+			"file_d",
+			"file_c",
+		}, fileList.Order)
+	})
+}
+
+func TestGetFilteredAccessibleFiles(t *testing.T) {
+	th := Setup(t)
+	th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
+	th.App.Srv().Store.System().Save(&model.System{
+		Name:  model.SystemLastAccessibleFileTime,
+		Value: "2",
+	})
+
+	defer th.TearDown()
+
+	var getFileWithCreateAt = func(at int64) *model.FileInfo {
+		return &model.FileInfo{CreateAt: at}
+	}
+
+	t.Run("ascending order returns correct files", func(t *testing.T) {
+		files := []*model.FileInfo{getFileWithCreateAt(0), getFileWithCreateAt(1), getFileWithCreateAt(2), getFileWithCreateAt(3), getFileWithCreateAt(4)}
+		filteredFiles, firstInaccessibleFileTime, appErr := th.App.getFilteredAccessibleFiles(files, filterFileOptions{assumeSortedCreatedAt: true})
+
+		require.Nil(t, appErr)
+		assert.Equal(t, []*model.FileInfo{getFileWithCreateAt(2), getFileWithCreateAt(3), getFileWithCreateAt(4)}, filteredFiles)
+		assert.Equal(t, int64(1), firstInaccessibleFileTime)
+	})
+
+	t.Run("descending order returns correct files", func(t *testing.T) {
+		files := []*model.FileInfo{getFileWithCreateAt(4), getFileWithCreateAt(3), getFileWithCreateAt(2), getFileWithCreateAt(1), getFileWithCreateAt(0)}
+		filteredFiles, firstInaccessibleFileTime, appErr := th.App.getFilteredAccessibleFiles(files, filterFileOptions{assumeSortedCreatedAt: true})
+
+		require.Nil(t, appErr)
+		assert.Equal(t, []*model.FileInfo{getFileWithCreateAt(4), getFileWithCreateAt(3), getFileWithCreateAt(2)}, filteredFiles)
+		assert.Equal(t, int64(1), firstInaccessibleFileTime)
+	})
+
+	t.Run("handles mixed create at ordering correctly if correct options given", func(t *testing.T) {
+		files := []*model.FileInfo{getFileWithCreateAt(4), getFileWithCreateAt(1), getFileWithCreateAt(0), getFileWithCreateAt(3), getFileWithCreateAt(2)}
+		filteredFiles, _, appErr := th.App.getFilteredAccessibleFiles(files, filterFileOptions{assumeSortedCreatedAt: false})
+
+		require.Nil(t, appErr)
+		assert.Equal(t, []*model.FileInfo{getFileWithCreateAt(4), getFileWithCreateAt(3), getFileWithCreateAt(2)}, filteredFiles)
+	})
+}
+
+func TestIsInaccessibleFile(t *testing.T) {
+	th := Setup(t)
+	th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
+	th.App.Srv().Store.System().Save(&model.System{
+		Name:  model.SystemLastAccessibleFileTime,
+		Value: "2",
+	})
+
+	defer th.TearDown()
+
+	file := &model.FileInfo{CreateAt: 3}
+	firstInaccessibleFileTime, appErr := th.App.isInaccessibleFile(file)
+	require.Nil(t, appErr)
+	assert.Equal(t, int64(0), firstInaccessibleFileTime)
+
+	file = &model.FileInfo{CreateAt: 1}
+	firstInaccessibleFileTime, appErr = th.App.isInaccessibleFile(file)
+	require.Nil(t, appErr)
+	assert.Equal(t, int64(1), firstInaccessibleFileTime)
+}
+
+func TestRemoveInaccessibleContentFromFilesSlice(t *testing.T) {
+	th := Setup(t)
+	th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
+	th.App.Srv().Store.System().Save(&model.System{
+		Name:  model.SystemLastAccessibleFileTime,
+		Value: "2",
+	})
+
+	defer th.TearDown()
+
+	var getFileWithCreateAt = func(at int64) *model.FileInfo {
+		return &model.FileInfo{CreateAt: at}
+	}
+
+	files := []*model.FileInfo{getFileWithCreateAt(4), getFileWithCreateAt(1), getFileWithCreateAt(0), getFileWithCreateAt(3), getFileWithCreateAt(2)}
+
+	_, appErr := th.App.removeInaccessibleContentFromFilesSlice(files)
+
+	require.Nil(t, appErr)
+	assert.Len(t, files, len(files))
+	for _, file := range files {
+		// Inaccessible files are archived
+		if file.CreateAt < 2 {
+			assert.True(t, file.Archived)
+		} else {
+			assert.False(t, file.Archived)
+		}
+	}
+}

app/file_test.go

@@ -16,9 +16,12 @@ import (
 	"github.com/stretchr/testify/mock"
 	"github.com/stretchr/testify/require"
 
+	eMocks "github.com/mattermost/mattermost-server/v6/einterfaces/mocks"
 	"github.com/mattermost/mattermost-server/v6/model"
 	"github.com/mattermost/mattermost-server/v6/services/searchengine/mocks"
 	filesStoreMocks "github.com/mattermost/mattermost-server/v6/shared/filestore/mocks"
+	"github.com/mattermost/mattermost-server/v6/store"
+	storemocks "github.com/mattermost/mattermost-server/v6/store/storetest/mocks"
 	"github.com/mattermost/mattermost-server/v6/utils/fileutils"
 )
 
@@ -553,3 +556,65 @@ func TestExtractContentFromFileInfo(t *testing.T) {
 	// Test that we don't process images.
 	require.NoError(t, app.ExtractContentFromFileInfo(fi))
 }
+
+func TestGetLastAccessibleFileTime(t *testing.T) {
+	th := SetupWithStoreMock(t)
+	defer th.TearDown()
+
+	r, err := th.App.GetLastAccessibleFileTime()
+	require.Nil(t, err)
+	assert.Equal(t, int64(0), r)
+
+	th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
+
+	mockStore := th.App.Srv().Store.(*storemocks.Store)
+
+	mockSystemStore := storemocks.SystemStore{}
+	mockStore.On("System").Return(&mockSystemStore)
+	mockSystemStore.On("GetByName", mock.Anything).Return(nil, store.NewErrNotFound("", ""))
+	r, err = th.App.GetLastAccessibleFileTime()
+	require.Nil(t, err)
+	assert.Equal(t, int64(0), r)
+
+	mockSystemStore = storemocks.SystemStore{}
+	mockStore.On("System").Return(&mockSystemStore)
+	mockSystemStore.On("GetByName", mock.Anything).Return(nil, errors.New("test"))
+	_, err = th.App.GetLastAccessibleFileTime()
+	require.NotNil(t, err)
+
+	mockSystemStore = storemocks.SystemStore{}
+	mockStore.On("System").Return(&mockSystemStore)
+	mockSystemStore.On("GetByName", mock.Anything).Return(&model.System{Name: model.SystemLastAccessibleFileTime, Value: "10"}, nil)
+	r, err = th.App.GetLastAccessibleFileTime()
+	require.Nil(t, err)
+	assert.Equal(t, int64(10), r)
+}
+
+func TestComputeLastAccessibleFileTime(t *testing.T) {
+	th := SetupWithStoreMock(t)
+	defer th.TearDown()
+
+	th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
+
+	cloud := &eMocks.CloudInterface{}
+	th.App.Srv().Cloud = cloud
+
+	cloud.Mock.On("GetCloudLimits", mock.Anything).Return(&model.ProductLimits{
+		Files: &model.FilesLimits{
+			TotalStorage: model.NewInt64(1),
+		},
+	}, nil)
+
+	mockStore := th.App.Srv().Store.(*storemocks.Store)
+	mockFileStore := storemocks.FileInfoStore{}
+	mockFileStore.On("GetUptoNSizeFileTime", mock.Anything).Return(int64(1), nil)
+	mockSystemStore := storemocks.SystemStore{}
+	mockSystemStore.On("SaveOrUpdate", mock.Anything).Return(nil)
+	mockStore.On("FileInfo").Return(&mockFileStore)
+	mockStore.On("System").Return(&mockSystemStore)
+
+	err := th.App.ComputeLastAccessibleFileTime()
+	require.NoError(t, err)
+
+	mockSystemStore.AssertCalled(t, "SaveOrUpdate", mock.Anything)
+}

app/import_functions.go

@@ -1225,7 +1225,7 @@ func (a *App) importAttachment(c request.CTX, data *imports.AttachmentImportData
 
 	// Go over existing files in the post and see if there already exists a file with the same name, size and hash. If so - skip it
 	if post.Id != "" {
-		oldFiles, err := a.GetFileInfosForPost(post.Id, true, false)
+		oldFiles, err := a.getFileInfosForPostIgnoreCloudLimit(post.Id, true, false)
 		if err != nil {
 			return nil, model.NewAppError("BulkImport", "app.import.attachment.file_upload.error", map[string]any{"FilePath": *data.Path}, "", http.StatusBadRequest)
 		}
@@ -1235,7 +1235,7 @@ func (a *App) importAttachment(c request.CTX, data *imports.AttachmentImportData
 			}
 			// check md5
 			newHash := sha1.Sum(fileData)
-			oldFileData, err := a.GetFile(oldFile.Id)
+			oldFileData, err := a.getFileIgnoreCloudLimit(oldFile.Id)
 			if err != nil {
 				return nil, model.NewAppError("BulkImport", "app.import.attachment.file_upload.error", map[string]any{"FilePath": *data.Path}, "", http.StatusBadRequest)
 			}

app/opentracing/opentracing_layer.go

@@ -1783,6 +1783,28 @@ func (a *OpenTracingAppLayer) CompleteSwitchWithOAuth(service string, userData i
 	return resultVar0, resultVar1
 }
 
+func (a *OpenTracingAppLayer) ComputeLastAccessibleFileTime() error {
+	origCtx := a.ctx
+	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.ComputeLastAccessibleFileTime")
+
+	a.ctx = newCtx
+	a.app.Srv().Store.SetContext(newCtx)
+	defer func() {
+		a.app.Srv().Store.SetContext(origCtx)
+		a.ctx = origCtx
+	}()
+
+	defer span.Finish()
+	resultVar0 := a.app.ComputeLastAccessibleFileTime()
+
+	if resultVar0 != nil {
+		span.LogFields(spanlog.Error(resultVar0))
+		ext.Error.Set(span, true)
+	}
+
+	return resultVar0
+}
+
 func (a *OpenTracingAppLayer) ComputeLastAccessiblePostTime() error {
 	origCtx := a.ctx
 	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.ComputeLastAccessiblePostTime")
@@ -6053,7 +6075,7 @@ func (a *OpenTracingAppLayer) GetFileInfos(page int, perPage int, opt *model.Get
 	return resultVar0, resultVar1
 }
 
-func (a *OpenTracingAppLayer) GetFileInfosForPost(postID string, fromMaster bool, includeDeleted bool) ([]*model.FileInfo, *model.AppError) {
+func (a *OpenTracingAppLayer) GetFileInfosForPost(postID string, fromMaster bool, includeDeleted bool) ([]*model.FileInfo, int64, *model.AppError) {
 	origCtx := a.ctx
 	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.GetFileInfosForPost")
 
@@ -6065,14 +6087,14 @@ func (a *OpenTracingAppLayer) GetFileInfosForPost(postID string, fromMaster bool
 	}()
 
 	defer span.Finish()
-	resultVar0, resultVar1 := a.app.GetFileInfosForPost(postID, fromMaster, includeDeleted)
+	resultVar0, resultVar1, resultVar2 := a.app.GetFileInfosForPost(postID, fromMaster, includeDeleted)
 
-	if resultVar1 != nil {
-		span.LogFields(spanlog.Error(resultVar1))
+	if resultVar2 != nil {
+		span.LogFields(spanlog.Error(resultVar2))
 		ext.Error.Set(span, true)
 	}
 
-	return resultVar0, resultVar1
+	return resultVar0, resultVar1, resultVar2
 }
 
 func (a *OpenTracingAppLayer) GetFileInfosForPostWithMigration(postID string, includeDeleted bool) ([]*model.FileInfo, *model.AppError) {
@@ -6884,6 +6906,28 @@ func (a *OpenTracingAppLayer) GetKnownUsers(userID string) ([]string, *model.App
 	return resultVar0, resultVar1
 }
 
+func (a *OpenTracingAppLayer) GetLastAccessibleFileTime() (int64, *model.AppError) {
+	origCtx := a.ctx
+	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.GetLastAccessibleFileTime")
+
+	a.ctx = newCtx
+	a.app.Srv().Store.SetContext(newCtx)
+	defer func() {
+		a.app.Srv().Store.SetContext(origCtx)
+		a.ctx = origCtx
+	}()
+
+	defer span.Finish()
+	resultVar0, resultVar1 := a.app.GetLastAccessibleFileTime()
+
+	if resultVar1 != nil {
+		span.LogFields(spanlog.Error(resultVar1))
+		ext.Error.Set(span, true)
+	}
+
+	return resultVar0, resultVar1
+}
+
 func (a *OpenTracingAppLayer) GetLastAccessiblePostTime() (int64, *model.AppError) {
 	origCtx := a.ctx
 	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.GetLastAccessiblePostTime")

app/post.go

@@ -1558,12 +1558,12 @@ func (a *App) GetFileInfosForPostWithMigration(postID string, includeDeleted boo
 		close(pchan)
 	}()
 
-	infos, err := a.GetFileInfosForPost(postID, false, includeDeleted)
+	infos, firstInaccessibleFileTime, err := a.GetFileInfosForPost(postID, false, includeDeleted)
 	if err != nil {
 		return nil, err
 	}
 
-	if len(infos) == 0 {
+	if len(infos) == 0 && firstInaccessibleFileTime == 0 {
 		// No FileInfos were returned so check if they need to be created for this post
 		result := <-pchan
 		if result.NErr != nil {
@@ -1588,10 +1588,27 @@ func (a *App) GetFileInfosForPostWithMigration(postID string, includeDeleted boo
 	return infos, nil
 }
 
-func (a *App) GetFileInfosForPost(postID string, fromMaster bool, includeDeleted bool) ([]*model.FileInfo, *model.AppError) {
+// GetFileInfosForPost also returns firstInaccessibleFileTime based on cloud plan's limit.
+func (a *App) GetFileInfosForPost(postID string, fromMaster bool, includeDeleted bool) ([]*model.FileInfo, int64, *model.AppError) {
 	fileInfos, err := a.Srv().Store.FileInfo().GetForPost(postID, fromMaster, includeDeleted, true)
 	if err != nil {
-		return nil, model.NewAppError("GetFileInfosForPost", "app.file_info.get_for_post.app_error", nil, "", http.StatusInternalServerError).Wrap(err)
+		return nil, 0, model.NewAppError("GetFileInfosForPost", "app.file_info.get_for_post.app_error", nil, "", http.StatusInternalServerError).Wrap(err)
+	}
+
+	firstInaccessibleFileTime, appErr := a.removeInaccessibleContentFromFilesSlice(fileInfos)
+	if appErr != nil {
+		return nil, 0, appErr
+	}
+
+	a.generateMiniPreviewForInfos(fileInfos)
+
+	return fileInfos, firstInaccessibleFileTime, nil
+}
+
+func (a *App) getFileInfosForPostIgnoreCloudLimit(postID string, fromMaster bool, includeDeleted bool) ([]*model.FileInfo, *model.AppError) {
+	fileInfos, err := a.Srv().Store.FileInfo().GetForPost(postID, fromMaster, includeDeleted, true)
+	if err != nil {
+		return nil, model.NewAppError("getFileInfosForPostIgnoreCloudLimit", "app.file_info.get_for_post.app_error", nil, "", http.StatusInternalServerError).Wrap(err)
 	}
 
 	a.generateMiniPreviewForInfos(fileInfos)

app/post_metadata.go

@@ -123,7 +123,7 @@ func (a *App) PreparePostForClient(originalPost *model.Post, isNewPost, isEditPo
 	}
 
 	// Files
-	if fileInfos, err := a.getFileMetadataForPost(post, isNewPost || isEditPost); err != nil {
+	if fileInfos, _, err := a.getFileMetadataForPost(post, isNewPost || isEditPost); err != nil {
 		mlog.Warn("Failed to get files for a post", mlog.String("post_id", post.Id), mlog.Err(err))
 	} else {
 		post.Metadata.Files = fileInfos
@@ -210,9 +210,9 @@ func (a *App) SanitizePostListMetadataForUser(c request.CTX, postList *model.Pos
 	return clonedPostList, nil
 }
 
-func (a *App) getFileMetadataForPost(post *model.Post, fromMaster bool) ([]*model.FileInfo, *model.AppError) {
+func (a *App) getFileMetadataForPost(post *model.Post, fromMaster bool) ([]*model.FileInfo, int64, *model.AppError) {
 	if len(post.FileIds) == 0 {
-		return nil, nil
+		return nil, 0, nil
 	}
 
 	return a.GetFileInfosForPost(post.Id, fromMaster, false)

app/post_test.go

@@ -219,7 +219,7 @@ func TestAttachFilesToPost(t *testing.T) {
 		appErr := th.App.attachFilesToPost(post)
 		assert.Nil(t, appErr)
 
-		infos, appErr := th.App.GetFileInfosForPost(post.Id, false, false)
+		infos, _, appErr := th.App.GetFileInfosForPost(post.Id, false, false)
 		assert.Nil(t, appErr)
 		assert.Len(t, infos, 2)
 	})
@@ -247,7 +247,7 @@ func TestAttachFilesToPost(t *testing.T) {
 		appErr := th.App.attachFilesToPost(post)
 		assert.Nil(t, appErr)
 
-		infos, appErr := th.App.GetFileInfosForPost(post.Id, false, false)
+		infos, _, appErr := th.App.GetFileInfosForPost(post.Id, false, false)
 		assert.Nil(t, appErr)
 		assert.Len(t, infos, 1)
 		assert.Equal(t, info2.Id, infos[0].Id)

app/server.go

@@ -46,6 +46,7 @@ import (
 	"github.com/mattermost/mattermost-server/v6/jobs/extract_content"
 	"github.com/mattermost/mattermost-server/v6/jobs/import_delete"
 	"github.com/mattermost/mattermost-server/v6/jobs/import_process"
+	"github.com/mattermost/mattermost-server/v6/jobs/last_accessible_file"
 	"github.com/mattermost/mattermost-server/v6/jobs/last_accessible_post"
 	"github.com/mattermost/mattermost-server/v6/jobs/migrations"
 	"github.com/mattermost/mattermost-server/v6/jobs/notify_admin"
@@ -1870,6 +1871,12 @@ func (s *Server) initJobs() {
 		last_accessible_post.MakeScheduler(s.Jobs, s.License()),
 	)
 
+	s.Jobs.RegisterJobType(
+		model.JobTypeLastAccessibleFile,
+		last_accessible_file.MakeWorker(s.Jobs, s.License(), New(ServerConnector(s.Channels()))),
+		last_accessible_file.MakeScheduler(s.Jobs, s.License()),
+	)
+
 	s.Jobs.RegisterJobType(
 		model.JobTypeUpgradeNotifyAdmin,
 		notify_admin.MakeUpgradeNotifyWorker(s.Jobs, s.License(), New(ServerConnector(s.Channels()))),

i18n/en.json

@@ -4987,6 +4987,10 @@
     "id": "app.export.zip_create.error",
     "translation": "Failed to add file to zip archive during export."
   },
+  {
+    "id": "app.file.cloud.get.app_error",
+    "translation": "Can not fetch the file as it is past the cloud plan's limit."
+  },
   {
     "id": "app.file_info.get.app_error",
     "translation": "Unable to get the file info."
@@ -5639,6 +5643,10 @@
     "id": "app.job.update.app_error",
     "translation": "Unable to update the job."
   },
+  {
+    "id": "app.last_accessible_file.app_error",
+    "translation": "Error fetching last accessible file"
+  },
   {
     "id": "app.last_accessible_post.app_error",
     "translation": "Error fetching last accessible post"

jobs/last_accessible_file/scheduler.go

@@ -0,0 +1,24 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+package last_accessible_file
+
+import (
+	"strconv"
+	"time"
+
+	"github.com/mattermost/mattermost-server/v6/jobs"
+	"github.com/mattermost/mattermost-server/v6/model"
+	"github.com/mattermost/mattermost-server/v6/shared/mlog"
+)
+
+const schedFreq = 2 * time.Hour
+
+func MakeScheduler(jobServer *jobs.JobServer, license *model.License) model.Scheduler {
+	isEnabled := func(cfg *model.Config) bool {
+		enabled := license != nil && *license.Features.Cloud
+		mlog.Debug("Scheduler: isEnabled: "+strconv.FormatBool(enabled), mlog.String("scheduler", model.JobTypeLastAccessibleFile))
+		return enabled
+	}
+	return jobs.NewPeriodicScheduler(jobServer, model.JobTypeLastAccessibleFile, schedFreq, isEnabled)
+}

jobs/last_accessible_file/worker.go

@@ -0,0 +1,28 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+package last_accessible_file
+
+import (
+	"github.com/mattermost/mattermost-server/v6/jobs"
+	"github.com/mattermost/mattermost-server/v6/model"
+)
+
+const (
+	JobName = "LastAccessibleFile"
+)
+
+type AppIface interface {
+	ComputeLastAccessibleFileTime() error
+}
+
+func MakeWorker(jobServer *jobs.JobServer, license *model.License, app AppIface) model.Worker {
+	isEnabled := func(_ *model.Config) bool {
+		return license != nil && *license.Features.Cloud
+	}
+	execute := func(_ *model.Job) error {
+		return app.ComputeLastAccessibleFileTime()
+	}
+	worker := jobs.NewSimpleWorker(JobName, jobServer, execute, isEnabled)
+	return worker
+}

model/client4.go

@@ -35,6 +35,7 @@ const (
 	HeaderRequestedWith             = "X-Requested-With"
 	HeaderRequestedWithXML          = "XMLHttpRequest"
 	HeaderFirstInaccessiblePostTime = "First-Inaccessible-Post-Time"
+	HeaderFirstInaccessibleFileTime = "First-Inaccessible-File-Time"
 	HeaderRange                     = "Range"
 	STATUS                          = "status"
 	StatusOk                        = "OK"

model/file_info.go

@@ -188,3 +188,17 @@ func GetEtagForFileInfos(infos []*FileInfo) string {
 
 	return Etag(infos[0].PostId, maxUpdateAt)
 }
+
+func (fi *FileInfo) MakeContentInaccessible() {
+	if fi == nil {
+		return
+	}
+
+	fi.Archived = true
+	fi.Content = ""
+	fi.HasPreviewImage = false
+	fi.MiniPreview = nil
+	fi.Path = ""
+	fi.PreviewPath = ""
+	fi.ThumbnailPath = ""
+}

model/file_info_list.go

@@ -12,6 +12,8 @@ type FileInfoList struct {
 	FileInfos      map[string]*FileInfo `json:"file_infos"`
 	NextFileInfoId string               `json:"next_file_info_id"`
 	PrevFileInfoId string               `json:"prev_file_info_id"`
+	// If there are inaccessible files, FirstInaccessibleFileTime is the time of the latest inaccessible file
+	FirstInaccessibleFileTime int64 `json:"first_inaccessible_file_time"`
 }
 
 func NewFileInfoList() *FileInfoList {

model/job.go

@@ -28,6 +28,7 @@ const (
 	JobTypeResendInvitationEmail        = "resend_invitation_email"
 	JobTypeExtractContent               = "extract_content"
 	JobTypeLastAccessiblePost           = "last_accessible_post"
+	JobTypeLastAccessibleFile           = "last_accessible_file"
 	JobTypeUpgradeNotifyAdmin           = "upgrade_notify_admin"
 	JobTypeTrialNotifyAdmin             = "trial_notify_admin"
 
@@ -59,6 +60,7 @@ var AllJobTypes = [...]string{
 	JobTypeCloud,
 	JobTypeExtractContent,
 	JobTypeLastAccessiblePost,
+	JobTypeLastAccessibleFile,
 }
 
 type Job struct {

model/system.go

@@ -32,6 +32,7 @@ const (
 	SystemFirstAdminVisitMarketplace       = "FirstAdminVisitMarketplace"
 	SystemFirstAdminSetupComplete          = "FirstAdminSetupComplete"
 	SystemLastAccessiblePostTime           = "LastAccessiblePostTime"
+	SystemLastAccessibleFileTime           = "LastAccessibleFileTime"
 	AwsMeteringReportInterval              = 1
 	AwsMeteringDimensionUsageHrs           = "UsageHrs"
 )

store/opentracinglayer/opentracinglayer.go

@@ -3527,6 +3527,24 @@ func (s *OpenTracingLayerFileInfoStore) GetStorageUsage(allowFromCache bool, inc
 	return result, err
 }
 
+func (s *OpenTracingLayerFileInfoStore) GetUptoNSizeFileTime(n int64) (int64, error) {
+	origCtx := s.Root.Store.Context()
+	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "FileInfoStore.GetUptoNSizeFileTime")
+	s.Root.Store.SetContext(newCtx)
+	defer func() {
+		s.Root.Store.SetContext(origCtx)
+	}()
+
+	defer span.Finish()
+	result, err := s.FileInfoStore.GetUptoNSizeFileTime(n)
+	if err != nil {
+		span.LogFields(spanlog.Error(err))
+		ext.Error.Set(span, true)
+	}
+
+	return result, err
+}
+
 func (s *OpenTracingLayerFileInfoStore) GetWithOptions(page int, perPage int, opt *model.GetFileInfosOptions) ([]*model.FileInfo, error) {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "FileInfoStore.GetWithOptions")

store/retrylayer/retrylayer.go

@@ -3957,6 +3957,27 @@ func (s *RetryLayerFileInfoStore) GetStorageUsage(allowFromCache bool, includeDe
 
 }
 
+func (s *RetryLayerFileInfoStore) GetUptoNSizeFileTime(n int64) (int64, error) {
+
+	tries := 0
+	for {
+		result, err := s.FileInfoStore.GetUptoNSizeFileTime(n)
+		if err == nil {
+			return result, nil
+		}
+		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
+		}
+		timepkg.Sleep(100 * timepkg.Millisecond)
+	}
+
+}
+
 func (s *RetryLayerFileInfoStore) GetWithOptions(page int, perPage int, opt *model.GetFileInfosOptions) ([]*model.FileInfo, error) {
 
 	tries := 0

store/sqlstore/file_info_store.go

@@ -753,3 +753,49 @@ func (fs SqlFileInfoStore) GetStorageUsage(allowFromCache, includeDeleted bool)
 	}
 	return size, nil
 }
+
+// GetUptoNSizeFileTime returns the CreateAt time of the last accessible file with a running-total size upto n bytes.
+func (fs *SqlFileInfoStore) GetUptoNSizeFileTime(n int64) (int64, error) {
+	if n <= 0 {
+		return 0, errors.New("n can't be less than 1")
+	}
+
+	var sizeSubQuery sq.SelectBuilder
+	// Separate query for MySql, as current min-version 5.x doesn't support window-functions
+	if fs.DriverName() == model.DatabaseDriverMysql {
+		sizeSubQuery = sq.
+			Select("(@runningSum := @runningSum + fi.Size) RunningTotal", "fi.CreateAt").
+			From("FileInfo fi").
+			Join("(SELECT @runningSum := 0) as tmp").
+			Where(sq.Eq{"fi.DeleteAt": 0}).
+			OrderBy("fi.CreateAt DESC, fi.Id")
+	} else {
+		sizeSubQuery = sq.
+			Select("SUM(fi.Size) OVER(ORDER BY CreateAt DESC, fi.Id) RunningTotal", "fi.CreateAt").
+			From("FileInfo fi").
+			Where(sq.Eq{"fi.DeleteAt": 0})
+	}
+
+	builder := fs.getQueryBuilder().
+		Select("fi2.CreateAt").
+		FromSelect(sizeSubQuery, "fi2").
+		Where(sq.LtOrEq{"fi2.RunningTotal": n}).
+		OrderBy("fi2.CreateAt").
+		Limit(1)
+
+	query, queryArgs, err := builder.ToSql()
+	if err != nil {
+		return 0, errors.Wrap(err, "GetUptoNSizeFileTime_tosql")
+	}
+
+	var createAt int64
+	if err := fs.GetReplicaX().Get(&createAt, query, queryArgs...); err != nil {
+		if err == sql.ErrNoRows {
+			return 0, store.NewErrNotFound("File", "none")
+		}
+
+		return 0, errors.Wrapf(err, "failed to get the File for size upto=%d", n)
+	}
+
+	return createAt, nil
+}

store/store.go

@@ -698,6 +698,8 @@ type FileInfoStore interface {
 	GetFilesBatchForIndexing(startTime int64, startFileID string, limit int) ([]*model.FileForIndexing, error)
 	ClearCaches()
 	GetStorageUsage(allowFromCache, includeDeleted bool) (int64, error)
+	// GetUptoNSizeFileTime returns the CreateAt time of the last accessible file with a running-total size upto n bytes.
+	GetUptoNSizeFileTime(n int64) (int64, error)
 }
 
 type UploadSessionStore interface {

store/storetest/file_info_store.go

@@ -11,6 +11,7 @@ import (
 
 	"github.com/mattermost/mattermost-server/v6/model"
 	"github.com/mattermost/mattermost-server/v6/store"
+	"github.com/mattermost/mattermost-server/v6/utils"
 
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -30,6 +31,7 @@ func TestFileInfoStore(t *testing.T, ss store.Store) {
 	t.Run("GetFilesBatchForIndexing", func(t *testing.T) { testFileInfoStoreGetFilesBatchForIndexing(t, ss) })
 	t.Run("CountAll", func(t *testing.T) { testFileInfoStoreCountAll(t, ss) })
 	t.Run("GetStorageUsage", func(t *testing.T) { testFileInfoGetStorageUsage(t, ss) })
+	t.Run("GetUptoNSizeFileTime", func(t *testing.T) { testGetUptoNSizeFileTime(t, ss) })
 }
 
 func testFileInfoSaveGet(t *testing.T, ss store.Store) {
@@ -772,3 +774,71 @@ func testFileInfoGetStorageUsage(t *testing.T, ss store.Store) {
 	require.NoError(t, err)
 	require.Equal(t, int64(30), usage)
 }
+
+func testGetUptoNSizeFileTime(t *testing.T, ss store.Store) {
+	_, err := ss.FileInfo().GetUptoNSizeFileTime(0)
+	assert.Error(t, err)
+	_, err = ss.FileInfo().GetUptoNSizeFileTime(-1)
+	assert.Error(t, err)
+
+	_, err = ss.FileInfo().PermanentDeleteBatch(model.GetMillis(), 100000)
+	require.NoError(t, err)
+
+	diff := int64(10000)
+	now := utils.MillisFromTime(time.Now()) + diff
+
+	f1, err := ss.FileInfo().Save(&model.FileInfo{
+		PostId:    model.NewId(),
+		CreatorId: model.NewId(),
+		Size:      10,
+		Path:      "file1.txt",
+		CreateAt:  now,
+	})
+	require.NoError(t, err)
+	now = now + diff
+	f2, err := ss.FileInfo().Save(&model.FileInfo{
+		PostId:    model.NewId(),
+		CreatorId: model.NewId(),
+		Size:      10,
+		Path:      "file2.txt",
+		CreateAt:  now,
+	})
+	require.NoError(t, err)
+	now = now + diff
+	f3, err := ss.FileInfo().Save(&model.FileInfo{
+		PostId:    model.NewId(),
+		CreatorId: model.NewId(),
+		Size:      10,
+		Path:      "file3.txt",
+		CreateAt:  now,
+	})
+	require.NoError(t, err)
+	now = now + diff
+	_, err = ss.FileInfo().Save(&model.FileInfo{
+		PostId:    model.NewId(),
+		CreatorId: model.NewId(),
+		Size:      10,
+		Path:      "file4.txt",
+		CreateAt:  now,
+	})
+	require.NoError(t, err)
+
+	createAt, err := ss.FileInfo().GetUptoNSizeFileTime(20)
+	require.NoError(t, err)
+	assert.Equal(t, f3.CreateAt, createAt)
+
+	_, err = ss.FileInfo().GetUptoNSizeFileTime(5)
+	assert.Error(t, err)
+	assert.IsType(t, &store.ErrNotFound{}, err)
+
+	createAt, err = ss.FileInfo().GetUptoNSizeFileTime(1000)
+	require.NoError(t, err)
+	assert.Equal(t, f1.CreateAt, createAt)
+
+	_, err = ss.FileInfo().DeleteForPost(f3.PostId)
+	require.NoError(t, err)
+
+	createAt, err = ss.FileInfo().GetUptoNSizeFileTime(20)
+	require.NoError(t, err)
+	assert.Equal(t, f2.CreateAt, createAt)
+}

store/storetest/mocks/FileInfoStore.go

@@ -257,6 +257,27 @@ func (_m *FileInfoStore) GetStorageUsage(allowFromCache bool, includeDeleted boo
 	return r0, r1
 }
 
+// GetUptoNSizeFileTime provides a mock function with given fields: n
+func (_m *FileInfoStore) GetUptoNSizeFileTime(n int64) (int64, error) {
+	ret := _m.Called(n)
+
+	var r0 int64
+	if rf, ok := ret.Get(0).(func(int64) int64); ok {
+		r0 = rf(n)
+	} else {
+		r0 = ret.Get(0).(int64)
+	}
+
+	var r1 error
+	if rf, ok := ret.Get(1).(func(int64) error); ok {
+		r1 = rf(n)
+	} else {
+		r1 = ret.Error(1)
+	}
+
+	return r0, r1
+}
+
 // GetWithOptions provides a mock function with given fields: page, perPage, opt
 func (_m *FileInfoStore) GetWithOptions(page int, perPage int, opt *model.GetFileInfosOptions) ([]*model.FileInfo, error) {
 	ret := _m.Called(page, perPage, opt)

store/timerlayer/timerlayer.go

@@ -3222,6 +3222,22 @@ func (s *TimerLayerFileInfoStore) GetStorageUsage(allowFromCache bool, includeDe
 	return result, err
 }
 
+func (s *TimerLayerFileInfoStore) GetUptoNSizeFileTime(n int64) (int64, error) {
+	start := time.Now()
+
+	result, err := s.FileInfoStore.GetUptoNSizeFileTime(n)
+
+	elapsed := float64(time.Since(start)) / float64(time.Second)
+	if s.Root.Metrics != nil {
+		success := "false"
+		if err == nil {
+			success = "true"
+		}
+		s.Root.Metrics.ObserveStoreMethodDuration("FileInfoStore.GetUptoNSizeFileTime", success, elapsed)
+	}
+	return result, err
+}
+
 func (s *TimerLayerFileInfoStore) GetWithOptions(page int, perPage int, opt *model.GetFileInfosOptions) ([]*model.FileInfo, error) {
 	start := time.Now()