diff --git a/server/channels/app/app_iface.go b/server/channels/app/app_iface.go
index bfe207ad01..c93a9fb17e 100644
--- a/server/channels/app/app_iface.go
+++ b/server/channels/app/app_iface.go
@@ -566,7 +566,7 @@ type AppIface interface {
 	ExportFileExists(path string) (bool, *model.AppError)
 	ExportFileModTime(path string) (time.Time, *model.AppError)
 	ExportPermissions(w io.Writer) error
-	ExtractContentFromFileInfo(fileInfo *model.FileInfo) error
+	ExtractContentFromFileInfo(rctx request.CTX, fileInfo *model.FileInfo) error
 	FetchSamlMetadataFromIdp(url string) ([]byte, *model.AppError)
 	FileBackend() filestore.FileBackend
 	FileExists(path string) (bool, *model.AppError)
diff --git a/server/channels/app/file.go b/server/channels/app/file.go
index bff245762a..d65b54981a 100644
--- a/server/channels/app/file.go
+++ b/server/channels/app/file.go
@@ -757,7 +757,7 @@ func (a *App) UploadFileX(c *request.Context, channelID, name string, input io.R
 
 	if written > t.maxFileSize {
 		if fileErr := a.RemoveFile(t.fileinfo.Path); fileErr != nil {
-			mlog.Error("Failed to remove file", mlog.Err(fileErr))
+			c.Logger().Error("Failed to remove file", mlog.Err(fileErr))
 		}
 		return nil, t.newAppError("api.file.upload_file.too_large_detailed.app_error", http.StatusRequestEntityTooLarge, "Length", t.ContentLength, "Limit", t.maxFileSize)
 	}
@@ -796,10 +796,11 @@ func (a *App) UploadFileX(c *request.Context, channelID, name string, input io.R
 
 	if *a.Config().FileSettings.ExtractContent {
 		infoCopy := *t.fileinfo
+		crctx := c.Clone()
 		a.Srv().GoBuffered(func() {
-			err := a.ExtractContentFromFileInfo(&infoCopy)
+			err := a.ExtractContentFromFileInfo(crctx, &infoCopy)
 			if err != nil {
-				mlog.Error("Failed to extract file content", mlog.Err(err), mlog.String("fileInfoId", infoCopy.Id))
+				crctx.Logger().Error("Failed to extract file content", mlog.Err(err), mlog.String("fileInfoId", infoCopy.Id))
 			}
 		})
 	}
@@ -1047,10 +1048,11 @@ func (a *App) DoUploadFileExpectModification(c request.CTX, now time.Time, rawTe
 
 	if *a.Config().FileSettings.ExtractContent {
 		infoCopy := *info
+		crctx := c.Clone()
 		a.Srv().GoBuffered(func() {
-			err := a.ExtractContentFromFileInfo(&infoCopy)
+			err := a.ExtractContentFromFileInfo(crctx, &infoCopy)
 			if err != nil {
-				mlog.Error("Failed to extract file content", mlog.Err(err), mlog.String("fileInfoId", infoCopy.Id))
+				crctx.Logger().Error("Failed to extract file content", mlog.Err(err), mlog.String("fileInfoId", infoCopy.Id))
 			}
 		})
 	}
@@ -1442,7 +1444,7 @@ func (a *App) SearchFilesInTeamForUser(c *request.Context, terms string, userId
 	return fileInfoSearchResults, a.filterInaccessibleFiles(fileInfoSearchResults, filterFileOptions{assumeSortedCreatedAt: true})
 }
 
-func (a *App) ExtractContentFromFileInfo(fileInfo *model.FileInfo) error {
+func (a *App) ExtractContentFromFileInfo(rctx request.CTX, fileInfo *model.FileInfo) error {
 	// We don't process images.
 	if fileInfo.IsImage() {
 		return nil
@@ -1453,7 +1455,7 @@ func (a *App) ExtractContentFromFileInfo(fileInfo *model.FileInfo) error {
 		return errors.Wrap(aerr, "failed to open file for extract file content")
 	}
 	defer file.Close()
-	text, err := docextractor.Extract(fileInfo.Name, file, docextractor.ExtractSettings{
+	text, err := docextractor.Extract(rctx.Logger(), fileInfo.Name, file, docextractor.ExtractSettings{
 		ArchiveRecursion: *a.Config().FileSettings.ArchiveRecursion,
 	})
 	if err != nil {
diff --git a/server/channels/app/file_test.go b/server/channels/app/file_test.go
index 19f34befac..fd783c4a99 100644
--- a/server/channels/app/file_test.go
+++ b/server/channels/app/file_test.go
@@ -17,6 +17,7 @@ import (
 	"github.com/stretchr/testify/require"
 
 	"github.com/mattermost/mattermost/server/public/model"
+	"github.com/mattermost/mattermost/server/public/shared/request"
 	"github.com/mattermost/mattermost/server/v8/channels/store"
 	storemocks "github.com/mattermost/mattermost/server/v8/channels/store/storetest/mocks"
 	"github.com/mattermost/mattermost/server/v8/channels/utils/fileutils"
@@ -555,7 +556,7 @@ func TestExtractContentFromFileInfo(t *testing.T) {
 	}
 
 	// Test that we don't process images.
-	require.NoError(t, app.ExtractContentFromFileInfo(fi))
+	require.NoError(t, app.ExtractContentFromFileInfo(request.TestContext(t), fi))
 }
 
 func TestGetLastAccessibleFileTime(t *testing.T) {
diff --git a/server/channels/app/opentracing/opentracing_layer.go b/server/channels/app/opentracing/opentracing_layer.go
index d20daec986..e576ecd0f0 100644
--- a/server/channels/app/opentracing/opentracing_layer.go
+++ b/server/channels/app/opentracing/opentracing_layer.go
@@ -4248,7 +4248,7 @@ func (a *OpenTracingAppLayer) ExtendSessionExpiryIfNeeded(session *model.Session
 	return resultVar0
 }
 
-func (a *OpenTracingAppLayer) ExtractContentFromFileInfo(fileInfo *model.FileInfo) error {
+func (a *OpenTracingAppLayer) ExtractContentFromFileInfo(rctx request.CTX, fileInfo *model.FileInfo) error {
 	origCtx := a.ctx
 	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.ExtractContentFromFileInfo")
 
@@ -4260,7 +4260,7 @@ func (a *OpenTracingAppLayer) ExtractContentFromFileInfo(fileInfo *model.FileInf
 	}()
 
 	defer span.Finish()
-	resultVar0 := a.app.ExtractContentFromFileInfo(fileInfo)
+	resultVar0 := a.app.ExtractContentFromFileInfo(rctx, fileInfo)
 
 	if resultVar0 != nil {
 		span.LogFields(spanlog.Error(resultVar0))
diff --git a/server/channels/app/upload.go b/server/channels/app/upload.go
index b0e27dc2d5..3a0f231428 100644
--- a/server/channels/app/upload.go
+++ b/server/channels/app/upload.go
@@ -318,17 +318,18 @@ func (a *App) UploadData(c request.CTX, us *model.UploadSession, rd io.Reader) (
 
 	if *a.Config().FileSettings.ExtractContent {
 		infoCopy := *info
+		crctx := c.Clone()
 		a.Srv().Go(func() {
-			err := a.ExtractContentFromFileInfo(&infoCopy)
+			err := a.ExtractContentFromFileInfo(crctx, &infoCopy)
 			if err != nil {
-				mlog.Error("Failed to extract file content", mlog.Err(err), mlog.String("fileInfoId", infoCopy.Id))
+				crctx.Logger().Error("Failed to extract file content", mlog.Err(err), mlog.String("fileInfoId", infoCopy.Id))
 			}
 		})
 	}
 
 	// delete upload session
 	if storeErr := a.Srv().Store().UploadSession().Delete(us.Id); storeErr != nil {
-		mlog.Warn("Failed to delete UploadSession", mlog.Err(storeErr))
+		c.Logger().Warn("Failed to delete UploadSession", mlog.Err(storeErr))
 	}
 
 	return info, nil
diff --git a/server/channels/jobs/extract_content/worker.go b/server/channels/jobs/extract_content/worker.go
index 25b7d988f4..dbdab9e407 100644
--- a/server/channels/jobs/extract_content/worker.go
+++ b/server/channels/jobs/extract_content/worker.go
@@ -8,6 +8,7 @@ import (
 
 	"github.com/mattermost/mattermost/server/public/model"
 	"github.com/mattermost/mattermost/server/public/shared/mlog"
+	"github.com/mattermost/mattermost/server/public/shared/request"
 	"github.com/mattermost/mattermost/server/v8/channels/jobs"
 	"github.com/mattermost/mattermost/server/v8/channels/store"
 )
@@ -20,7 +21,7 @@ var ignoredFiles = map[string]bool{
 }
 
 type AppIface interface {
-	ExtractContentFromFileInfo(fileInfo *model.FileInfo) error
+	ExtractContentFromFileInfo(rctx request.CTX, fileInfo *model.FileInfo) error
 }
 
 func MakeWorker(jobServer *jobs.JobServer, app AppIface, store store.Store) *jobs.SimpleWorker {
@@ -66,7 +67,8 @@ func MakeWorker(jobServer *jobs.JobServer, app AppIface, store store.Store) *job
 			for _, fileInfo := range fileInfos {
 				if !ignoredFiles[fileInfo.Extension] {
 					logger.Debug("Extracting file", mlog.String("filename", fileInfo.Name), mlog.String("filepath", fileInfo.Path))
-					err = app.ExtractContentFromFileInfo(fileInfo)
+
+					err = app.ExtractContentFromFileInfo(request.EmptyContext(logger), fileInfo)
 					if err != nil {
 						logger.Warn("Failed to extract file content", mlog.Err(err), mlog.String("file_info_id", fileInfo.Id))
 						nErrs++
diff --git a/server/platform/services/docextractor/archive.go b/server/platform/services/docextractor/archive.go
index 1c0e228afb..585fd29462 100644
--- a/server/platform/services/docextractor/archive.go
+++ b/server/platform/services/docextractor/archive.go
@@ -18,6 +18,10 @@ type archiveExtractor struct {
 	SubExtractor Extractor
 }
 
+func (ae *archiveExtractor) Name() string {
+	return "archiveExtractor"
+}
+
 func (ae *archiveExtractor) Match(filename string) bool {
 	_, err := archiver.ByExtension(filename)
 	return err == nil
diff --git a/server/platform/services/docextractor/combine.go b/server/platform/services/docextractor/combine.go
index 6cc978faa8..474b53faee 100644
--- a/server/platform/services/docextractor/combine.go
+++ b/server/platform/services/docextractor/combine.go
@@ -10,9 +10,14 @@ import (
 )
 
 type combineExtractor struct {
+	logger        mlog.LoggerIFace
 	SubExtractors []Extractor
 }
 
+func (ce *combineExtractor) Name() string {
+	return "combineExtractor"
+}
+
 func (ce *combineExtractor) Add(extractor Extractor) {
 	ce.SubExtractors = append(ce.SubExtractors, extractor)
 }
@@ -32,7 +37,7 @@ func (ce *combineExtractor) Extract(filename string, r io.ReadSeeker) (string, e
 			r.Seek(0, io.SeekStart)
 			text, err := extractor.Extract(filename, r)
 			if err != nil {
-				mlog.Warn("unable to extract file content", mlog.Err(err))
+				ce.logger.Warn("Unable to extract file content", mlog.String("file_name", filename), mlog.String("extractor", extractor.Name()), mlog.Err(err))
 				continue
 			}
 			return text, nil
diff --git a/server/platform/services/docextractor/docextractor.go b/server/platform/services/docextractor/docextractor.go
index 5c05af7a22..557d03303e 100644
--- a/server/platform/services/docextractor/docextractor.go
+++ b/server/platform/services/docextractor/docextractor.go
@@ -5,6 +5,8 @@ package docextractor
 
 import (
 	"io"
+
+	"github.com/mattermost/mattermost/server/public/shared/mlog"
 )
 
 // ExtractSettings defines the features enabled/disable during the document text extraction.
@@ -15,13 +17,15 @@ type ExtractSettings struct {
 }
 
 // Extract extract the text from a document using the system default extractors
-func Extract(filename string, r io.ReadSeeker, settings ExtractSettings) (string, error) {
-	return ExtractWithExtraExtractors(filename, r, settings, []Extractor{})
+func Extract(logger mlog.LoggerIFace, filename string, r io.ReadSeeker, settings ExtractSettings) (string, error) {
+	return ExtractWithExtraExtractors(logger, filename, r, settings, []Extractor{})
 }
 
 // ExtractWithExtraExtractors extract the text from a document using the provided extractors beside the system default extractors.
-func ExtractWithExtraExtractors(filename string, r io.ReadSeeker, settings ExtractSettings, extraExtractors []Extractor) (string, error) {
-	enabledExtractors := &combineExtractor{}
+func ExtractWithExtraExtractors(logger mlog.LoggerIFace, filename string, r io.ReadSeeker, settings ExtractSettings, extraExtractors []Extractor) (string, error) {
+	enabledExtractors := &combineExtractor{
+		logger: logger,
+	}
 	for _, extraExtractor := range extraExtractors {
 		enabledExtractors.Add(extraExtractor)
 	}
diff --git a/server/platform/services/docextractor/docextractor_test.go b/server/platform/services/docextractor/docextractor_test.go
index 7cad5445e0..3ba93876fa 100644
--- a/server/platform/services/docextractor/docextractor_test.go
+++ b/server/platform/services/docextractor/docextractor_test.go
@@ -13,10 +13,13 @@ import (
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
+	"github.com/mattermost/mattermost/server/public/shared/mlog"
 	"github.com/mattermost/mattermost/server/v8/channels/utils/testutils"
 )
 
 func TestExtract(t *testing.T) {
+	logger := mlog.CreateConsoleTestLogger(t)
+
 	testCases := []struct {
 		Name         string
 		TestFileName string
@@ -127,7 +130,7 @@ func TestExtract(t *testing.T) {
 		t.Run(tc.Name, func(t *testing.T) {
 			data, err := testutils.ReadTestFile(tc.TestFileName)
 			require.NoError(t, err)
-			text, err := Extract(tc.TestFileName, bytes.NewReader(data), tc.Settings)
+			text, err := Extract(logger, tc.TestFileName, bytes.NewReader(data), tc.Settings)
 			if tc.ExpectError {
 				require.Error(t, err)
 			} else {
@@ -145,7 +148,7 @@ func TestExtract(t *testing.T) {
 	t.Run("Unsupported binary file", func(t *testing.T) {
 		data, err := testutils.ReadTestFile("testjpg.jpg")
 		require.NoError(t, err)
-		text, err := Extract("testjpg.jpg", bytes.NewReader(data), ExtractSettings{})
+		text, err := Extract(logger, "testjpg.jpg", bytes.NewReader(data), ExtractSettings{})
 		require.NoError(t, err)
 		require.Equal(t, "", text)
 	})
@@ -153,7 +156,7 @@ func TestExtract(t *testing.T) {
 	t.Run("Wrong docx extension", func(t *testing.T) {
 		data, err := testutils.ReadTestFile("sample-doc.pdf")
 		require.NoError(t, err)
-		text, err := Extract("sample-doc.docx", bytes.NewReader(data), ExtractSettings{})
+		text, err := Extract(logger, "sample-doc.docx", bytes.NewReader(data), ExtractSettings{})
 		require.NoError(t, err)
 		require.Equal(t, "", text)
 	})
@@ -161,6 +164,10 @@ func TestExtract(t *testing.T) {
 
 type customTestPdfExtractor struct{}
 
+func (te *customTestPdfExtractor) Name() string {
+	return "customTestPdfExtractor"
+}
+
 func (te *customTestPdfExtractor) Match(filename string) bool {
 	return strings.HasSuffix(filename, ".pdf")
 }
@@ -171,6 +178,10 @@ func (te *customTestPdfExtractor) Extract(filename string, r io.ReadSeeker) (str
 
 type failingExtractor struct{}
 
+func (te *failingExtractor) Name() string {
+	return "failingExtractor"
+}
+
 func (te *failingExtractor) Match(filename string) bool {
 	return true
 }
@@ -180,11 +191,12 @@ func (te *failingExtractor) Extract(filename string, r io.ReadSeeker) (string, e
 }
 
 func TestExtractWithExtraExtractors(t *testing.T) {
+	logger := mlog.CreateConsoleTestLogger(t)
 	t.Run("override existing extractor", func(t *testing.T) {
 		data, err := testutils.ReadTestFile("sample-doc.pdf")
 		require.NoError(t, err)
 
-		text, err := ExtractWithExtraExtractors("sample-doc.pdf", bytes.NewReader(data), ExtractSettings{}, []Extractor{&customTestPdfExtractor{}})
+		text, err := ExtractWithExtraExtractors(logger, "sample-doc.pdf", bytes.NewReader(data), ExtractSettings{}, []Extractor{&customTestPdfExtractor{}})
 		require.NoError(t, err)
 		require.Equal(t, text, "this is a text generated content")
 	})
@@ -193,7 +205,7 @@ func TestExtractWithExtraExtractors(t *testing.T) {
 		data, err := testutils.ReadTestFile("sample-doc.pdf")
 		require.NoError(t, err)
 
-		text, err := ExtractWithExtraExtractors("sample-doc.pdf", bytes.NewReader(data), ExtractSettings{}, []Extractor{&failingExtractor{}})
+		text, err := ExtractWithExtraExtractors(logger, "sample-doc.pdf", bytes.NewReader(data), ExtractSettings{}, []Extractor{&failingExtractor{}})
 		require.NoError(t, err)
 		assert.Contains(t, text, "simple")
 		assert.Contains(t, text, "document")
diff --git a/server/platform/services/docextractor/documents.go b/server/platform/services/docextractor/documents.go
index 3203df81bd..e6221805dc 100644
--- a/server/platform/services/docextractor/documents.go
+++ b/server/platform/services/docextractor/documents.go
@@ -26,6 +26,10 @@ var doconvConverterByExtensions = map[string]func(io.Reader) (string, map[string
 	"pdf": docconv.ConvertPDF,
 }
 
+func (de *documentExtractor) Name() string {
+	return "documentExtractor"
+}
+
 func (de *documentExtractor) Match(filename string) bool {
 	extension := strings.TrimPrefix(path.Ext(filename), ".")
 	_, ok := doconvConverterByExtensions[extension]
diff --git a/server/platform/services/docextractor/interface.go b/server/platform/services/docextractor/interface.go
index 6ea417914d..582fb0b502 100644
--- a/server/platform/services/docextractor/interface.go
+++ b/server/platform/services/docextractor/interface.go
@@ -11,4 +11,5 @@ import (
 type Extractor interface {
 	Match(filename string) bool
 	Extract(filename string, file io.ReadSeeker) (string, error)
+	Name() string
 }
diff --git a/server/platform/services/docextractor/mmpreview.go b/server/platform/services/docextractor/mmpreview.go
index b38e16c5af..51a261e233 100644
--- a/server/platform/services/docextractor/mmpreview.go
+++ b/server/platform/services/docextractor/mmpreview.go
@@ -36,6 +36,10 @@ func newMMPreviewExtractor(url string, secret string, pdfExtractor pdfExtractor)
 	return &mmPreviewExtractor{url: url, secret: secret, pdfExtractor: pdfExtractor}
 }
 
+func (mpe *mmPreviewExtractor) Name() string {
+	return "mmPreviewExtractor"
+}
+
 func (mpe *mmPreviewExtractor) Match(filename string) bool {
 	extension := strings.TrimPrefix(path.Ext(filename), ".")
 	return mmpreviewSupportedExtensions[extension]
diff --git a/server/platform/services/docextractor/pdf.go b/server/platform/services/docextractor/pdf.go
index baa7d6685e..67ba8ad274 100644
--- a/server/platform/services/docextractor/pdf.go
+++ b/server/platform/services/docextractor/pdf.go
@@ -17,6 +17,10 @@ import (
 
 type pdfExtractor struct{}
 
+func (pe *pdfExtractor) Name() string {
+	return "pdfExtractor"
+}
+
 func (pe *pdfExtractor) Match(filename string) bool {
 	supportedExtensions := map[string]bool{
 		"pdf": true,
diff --git a/server/platform/services/docextractor/plain.go b/server/platform/services/docextractor/plain.go
index e97bb1d0b8..8877c20b34 100644
--- a/server/platform/services/docextractor/plain.go
+++ b/server/platform/services/docextractor/plain.go
@@ -11,6 +11,10 @@ import (
 
 type plainExtractor struct{}
 
+func (pe *plainExtractor) Name() string {
+	return "plainExtractor"
+}
+
 func (pe *plainExtractor) Match(filename string) bool {
 	return true
 }