diff --git a/server/channels/api4/file_test.go b/server/channels/api4/file_test.go
index f0e7d9a98c..cf88da84a6 100644
--- a/server/channels/api4/file_test.go
+++ b/server/channels/api4/file_test.go
@@ -60,7 +60,8 @@ func fileBytes(t *testing.T, path string) []byte {
 }
 
 func testDoUploadFileRequest(t testing.TB, c *model.Client4, url string, blob []byte, contentType string,
-	contentLength int64) (*model.FileUploadResponse, *model.Response, error) {
+	contentLength int64,
+) (*model.FileUploadResponse, *model.Response, error) {
 	req, err := http.NewRequest("POST", c.APIURL+"/files"+url, bytes.NewReader(blob))
 	require.NoError(t, err)
 
@@ -390,6 +391,19 @@ func TestUploadFiles(t *testing.T) {
 			expectedImageMiniPreview:    []bool{true},
 			expectedCreatorId:           th.BasicUser.Id,
 		},
+		// 5MB+ JPEG
+		{
+			title:                       "Happy image thumbnail/preview 5MB+",
+			names:                       []string{"orientation_test_9.jpeg"},
+			expectedImageThumbnailNames: []string{"orientation_test_9_expected_thumb.jpeg"},
+			expectedImagePreviewNames:   []string{"orientation_test_9_expected_preview.jpeg"},
+			expectImage:                 true,
+			expectedImageWidths:         []int{4000},
+			expectedImageHeights:        []int{2667},
+			expectedImageHasPreview:     []bool{true},
+			expectedImageMiniPreview:    []bool{true},
+			expectedCreatorId:           th.BasicUser.Id,
+		},
 		// TIFF preview test
 		{
 			title:                       "Happy image thumbnail/preview 9",
diff --git a/server/channels/api4/team.go b/server/channels/api4/team.go
index 4b8b28908b..d9593fcc44 100644
--- a/server/channels/api4/team.go
+++ b/server/channels/api4/team.go
@@ -1664,7 +1664,6 @@ func getTeamIcon(c *Context, w http.ResponseWriter, r *http.Request) {
 	}
 
 	team, err := c.App.GetTeam(c.Params.TeamId)
-
 	if err != nil {
 		c.Err = err
 		return
@@ -1742,7 +1741,7 @@ func setTeamIcon(c *Context, w http.ResponseWriter, r *http.Request) {
 
 	imageData := imageArray[0]
 
-	if err := c.App.SetTeamIcon(c.Params.TeamId, imageData); err != nil {
+	if err := c.App.SetTeamIcon(c.AppContext, c.Params.TeamId, imageData); err != nil {
 		c.Err = err
 		return
 	}
diff --git a/server/channels/app/file.go b/server/channels/app/file.go
index 25f56e3ba1..94bece11bd 100644
--- a/server/channels/app/file.go
+++ b/server/channels/app/file.go
@@ -770,11 +770,8 @@ func (t *UploadFileTask) init(a *App) {
 // upload, returning a rejection error. In this case FileInfo would have
 // contained the last "good" FileInfo before the execution of that plugin.
 func (a *App) UploadFileX(c request.CTX, channelID, name string, input io.Reader,
-	opts ...func(*UploadFileTask)) (*model.FileInfo, *model.AppError) {
-	c = c.WithLogger(c.Logger().With(
-		mlog.String("file_name", name),
-	))
-
+	opts ...func(*UploadFileTask),
+) (*model.FileInfo, *model.AppError) {
 	t := &UploadFileTask{
 		Logger:         c.Logger(),
 		ChannelId:      filepath.Base(channelID),
@@ -790,6 +787,12 @@ func (a *App) UploadFileX(c request.CTX, channelID, name string, input io.Reader
 		o(t)
 	}
 
+	c = c.WithLogger(c.Logger().With(
+		mlog.String("file_name", name),
+		mlog.String("channel_id", channelID),
+		mlog.String("user_id", t.UserId),
+	))
+
 	if *a.Config().FileSettings.DriverName == "" {
 		return nil, t.newAppError("api.file.upload_file.storage.app_error", http.StatusNotImplemented)
 	}
@@ -880,14 +883,14 @@ func (t *UploadFileTask) preprocessImage() *model.AppError {
 	}
 
 	// If we fail to decode, return "as is".
-	w, h, err := imaging.GetDimensions(t.teeInput)
+	cfg, format, err := t.imgDecoder.DecodeConfig(t.teeInput)
 	if err != nil {
 		return nil
 	}
-	t.fileinfo.Width = w
-	t.fileinfo.Height = h
+	t.fileinfo.Width = cfg.Width
+	t.fileinfo.Height = cfg.Height
 
-	if err = checkImageResolutionLimit(w, h, t.maxImageRes); err != nil {
+	if err = checkImageResolutionLimit(cfg.Width, cfg.Height, t.maxImageRes); err != nil {
 		return t.newAppError("api.file.upload_file.large_image_detailed.app_error", http.StatusBadRequest)
 	}
 
@@ -899,12 +902,14 @@ func (t *UploadFileTask) preprocessImage() *model.AppError {
 	// check the image orientation with goexif; consume the bytes we
 	// already have first, then keep Tee-ing from input.
 	// TODO: try to reuse exif's .Raw buffer rather than Tee-ing
-	if t.imageOrientation, err = imaging.GetImageOrientation(io.MultiReader(bytes.NewReader(t.buf.Bytes()), t.teeInput)); err == nil &&
+	if t.imageOrientation, err = imaging.GetImageOrientation(io.MultiReader(bytes.NewReader(t.buf.Bytes()), t.teeInput), format); err == nil &&
 		(t.imageOrientation == imaging.RotatedCWMirrored ||
 			t.imageOrientation == imaging.RotatedCCW ||
 			t.imageOrientation == imaging.RotatedCCWMirrored ||
 			t.imageOrientation == imaging.RotatedCW) {
 		t.fileinfo.Width, t.fileinfo.Height = t.fileinfo.Height, t.fileinfo.Width
+	} else if err != nil {
+		t.Logger.Warn("Failed to get image orientation", mlog.Err(err))
 	}
 
 	// For animated GIFs disable the preview; since we have to Decode gifs
@@ -1045,12 +1050,14 @@ func (a *App) DoUploadFileExpectModification(c request.CTX, now time.Time, rawTe
 		return nil, data, err
 	}
 
-	if orientation, err := imaging.GetImageOrientation(bytes.NewReader(data)); err == nil &&
+	if orientation, err := imaging.GetImageOrientation(bytes.NewReader(data), info.MimeType); err == nil &&
 		(orientation == imaging.RotatedCWMirrored ||
 			orientation == imaging.RotatedCCW ||
 			orientation == imaging.RotatedCCWMirrored ||
 			orientation == imaging.RotatedCW) {
 		info.Width, info.Height = info.Height, info.Width
+	} else if err != nil {
+		c.Logger().Warn("Failed to get image orientation", mlog.Err(err))
 	}
 
 	info.Id = model.NewId()
@@ -1161,7 +1168,7 @@ func prepareImage(rctx request.CTX, imgDecoder *imaging.Decoder, imgData io.Read
 	imgData.Seek(0, io.SeekStart)
 
 	// Flip the image to be upright
-	orientation, err := imaging.GetImageOrientation(imgData)
+	orientation, err := imaging.GetImageOrientation(imgData, imgType)
 	if err != nil {
 		rctx.Logger().Debug("GetImageOrientation failed", mlog.Err(err))
 	}
diff --git a/server/channels/app/imaging/orientation.go b/server/channels/app/imaging/orientation.go
index 267f80bcce..98fcffac9d 100644
--- a/server/channels/app/imaging/orientation.go
+++ b/server/channels/app/imaging/orientation.go
@@ -4,12 +4,14 @@
 package imaging
 
 import (
+	"errors"
 	"fmt"
 	"image"
 	"io"
+	"strings"
 
 	"github.com/anthonynsimon/bild/transform"
-	"github.com/rwcarlsen/goexif/exif"
+	"github.com/bep/imagemeta"
 )
 
 const (
@@ -33,6 +35,8 @@ const (
 	RotatedCW
 )
 
+var errStopDecoding = fmt.Errorf("stop decoding")
+
 // MakeImageUpright changes the orientation of the given image.
 func MakeImageUpright(img image.Image, orientation int) image.Image {
 	switch orientation {
@@ -55,23 +59,101 @@ func MakeImageUpright(img image.Image, orientation int) image.Image {
 	}
 }
 
+type fwSeeker struct {
+	r   io.Reader
+	pos int64
+}
+
+func (f *fwSeeker) Read(p []byte) (int, error) {
+	n, err := f.r.Read(p)
+	if err != nil {
+		return n, err
+	}
+	f.pos += int64(n)
+	return n, nil
+}
+
+func (f *fwSeeker) Seek(offset int64, whence int) (int64, error) {
+	isForwardSeek := (whence == io.SeekStart && offset >= f.pos) ||
+		(whence == io.SeekCurrent && offset >= 0)
+
+	// We only support seeking forward.
+	if !isForwardSeek {
+		return 0, fmt.Errorf("seeking backwards is not supported")
+	}
+
+	toRead := offset
+	if whence == io.SeekStart {
+		toRead -= f.pos
+	}
+
+	// Seeking forward means we can simply discard the data.
+	n, err := io.CopyN(io.Discard, f.r, toRead)
+	if err != nil {
+		return n, fmt.Errorf("failed to seek: %w", err)
+	}
+
+	f.pos += n
+
+	return f.pos, nil
+}
+
 // GetImageOrientation reads the input data and returns the EXIF encoded
-// image orientation.
-func GetImageOrientation(input io.Reader) (int, error) {
-	exifData, err := exif.Decode(input)
-	if err != nil {
+// image orientation. Supported formats are JPEG, PNG, TIFF, and WebP.
+// Passing an io.ReadSeeker is preferable as we can't guarantee a plain
+// io.Reader will work for all formats (e.g. TIFF requires backwards seeking).
+func GetImageOrientation(input io.Reader, format string) (int, error) {
+	orientation := Upright
+
+	// Strip the "image/" prefix from the format in case it's a MIME type.
+	format, _ = strings.CutPrefix(format, "image/")
+
+	var imgFormat imagemeta.ImageFormat
+	switch format {
+	case "jpeg":
+		imgFormat = imagemeta.JPEG
+	case "png":
+		imgFormat = imagemeta.PNG
+	case "tiff":
+		imgFormat = imagemeta.TIFF
+	case "webp":
+		imgFormat = imagemeta.WebP
+	default:
+		// We don't support EXIF on any other format.
+		return orientation, fmt.Errorf("unsupported image format: %s", format)
+	}
+
+	var rs io.ReadSeeker
+	if r, ok := input.(io.ReadSeeker); ok {
+		rs = r
+	} else {
+		rs = &fwSeeker{r: input}
+	}
+
+	opts := imagemeta.Options{
+		R: rs,
+		HandleTag: func(tag imagemeta.TagInfo) error {
+			if tag.Tag == "Orientation" {
+				if o, ok := tag.Value.(uint16); ok {
+					orientation = int(o)
+					// Stop decoding after we've found the orientation tag]
+					// since it's the only one we care about.
+					return errStopDecoding
+				}
+			}
+			return nil
+		},
+		ShouldHandleTag: func(tag imagemeta.TagInfo) bool {
+			// We only care about the orientation tag.
+			return tag.Tag == "Orientation"
+		},
+		Sources:     imagemeta.EXIF, // We only care about EXIF data.
+		ImageFormat: imgFormat,
+	}
+
+	if err := imagemeta.Decode(opts); err != nil && !errors.Is(err, errStopDecoding) {
 		return Upright, fmt.Errorf("failed to decode exif data: %w", err)
 	}
 
-	tag, err := exifData.Get("Orientation")
-	if err != nil {
-		return Upright, fmt.Errorf("failed to get orientation field from exif data: %w", err)
-	}
-
-	orientation, err := tag.Int(0)
-	if err != nil {
-		return Upright, fmt.Errorf("failed to get value from exif tag: %w", err)
-	}
-
 	return orientation, nil
 }
diff --git a/server/channels/app/imaging/orientation_test.go b/server/channels/app/imaging/orientation_test.go
new file mode 100644
index 0000000000..862343c659
--- /dev/null
+++ b/server/channels/app/imaging/orientation_test.go
@@ -0,0 +1,199 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+package imaging
+
+import (
+	"bytes"
+	"fmt"
+	"io"
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/mattermost/mattermost/server/v8/channels/utils/fileutils"
+	"github.com/stretchr/testify/require"
+)
+
+func TestFwSeeker(t *testing.T) {
+	t.Run("Read", func(t *testing.T) {
+		data := []byte("hello world")
+		reader := bytes.NewReader(data)
+		seeker := &fwSeeker{r: reader}
+
+		// Read the first 5 bytes
+		buf := make([]byte, 5)
+		n, err := seeker.Read(buf)
+		require.NoError(t, err)
+		require.Equal(t, 5, n)
+		require.Equal(t, []byte("hello"), buf)
+
+		// Read the next 6 bytes
+		buf = make([]byte, 6)
+		n, err = seeker.Read(buf)
+		require.NoError(t, err)
+		require.Equal(t, 6, n)
+		require.Equal(t, []byte(" world"), buf)
+
+		// Try to read more, should get EOF
+		buf = make([]byte, 1)
+		n, err = seeker.Read(buf)
+		require.Equal(t, 0, n)
+		require.Equal(t, io.EOF, err)
+	})
+
+	t.Run("Seek forward from start", func(t *testing.T) {
+		data := []byte("hello world")
+		reader := bytes.NewReader(data)
+		seeker := &fwSeeker{r: reader}
+
+		// Seek forward 6 bytes
+		pos, err := seeker.Seek(6, io.SeekStart)
+		require.NoError(t, err)
+		require.Equal(t, int64(6), pos)
+
+		// Seeking from the same position should work
+		pos, err = seeker.Seek(6, io.SeekStart)
+		require.NoError(t, err)
+		require.Equal(t, int64(6), pos)
+
+		// Seeking again from start should work.
+		pos, err = seeker.Seek(7, io.SeekStart)
+		require.NoError(t, err)
+		require.Equal(t, int64(7), pos)
+
+		// Seeking backwards should not be supported
+		_, err = seeker.Seek(6, io.SeekStart)
+		require.EqualError(t, err, "seeking backwards is not supported")
+
+		// Read the remaining data
+		buf := make([]byte, 4)
+		n, err := seeker.Read(buf)
+		require.NoError(t, err)
+		require.Equal(t, 4, n)
+		require.Equal(t, []byte("orld"), buf)
+	})
+
+	t.Run("Seek forward from current", func(t *testing.T) {
+		data := []byte("hello world")
+		reader := bytes.NewReader(data)
+		seeker := &fwSeeker{r: reader}
+
+		// Read first 6 bytes
+		buf := make([]byte, 6)
+		n, err := seeker.Read(buf)
+		require.NoError(t, err)
+		require.Equal(t, 6, n)
+		require.Equal(t, []byte("hello "), buf)
+
+		// Seek forward 2 more bytes from current position
+		pos, err := seeker.Seek(2, io.SeekCurrent)
+		require.NoError(t, err)
+		require.Equal(t, int64(8), pos)
+
+		// Read the remaining data
+		buf = make([]byte, 3)
+		n, err = seeker.Read(buf)
+		require.NoError(t, err)
+		require.Equal(t, 3, n)
+		require.Equal(t, []byte("rld"), buf)
+	})
+
+	t.Run("Seek backward not supported", func(t *testing.T) {
+		data := []byte("hello world")
+		reader := bytes.NewReader(data)
+		seeker := &fwSeeker{r: reader}
+
+		// Try to seek backward
+		_, err := seeker.Seek(-1, io.SeekCurrent)
+		require.EqualError(t, err, "seeking backwards is not supported")
+
+		// Try to seek from end
+		_, err = seeker.Seek(0, io.SeekEnd)
+		require.EqualError(t, err, "seeking backwards is not supported")
+	})
+
+	t.Run("Seek beyond EOF", func(t *testing.T) {
+		data := []byte("hello")
+		reader := bytes.NewReader(data)
+		seeker := &fwSeeker{r: reader}
+
+		// Try to seek beyond EOF
+		n, err := seeker.Seek(10, io.SeekStart)
+		require.EqualError(t, err, "failed to seek: EOF")
+		require.Equal(t, int64(5), n) // Should have read until EOF (5 bytes)
+	})
+}
+
+func TestGetImageOrientation(t *testing.T) {
+	imgDir, ok := fileutils.FindDir("tests/exif_samples")
+	require.True(t, ok, "Failed to find exif samples directory")
+
+	// Define orientations and their corresponding file prefixes
+	orientations := map[string]int{
+		"up":             Upright,
+		"up-mirrored":    UprightMirrored,
+		"down":           UpsideDown,
+		"down-mirrored":  UpsideDownMirrored,
+		"left":           RotatedCCW,
+		"left-mirrored":  RotatedCWMirrored,
+		"right":          RotatedCW,
+		"right-mirrored": RotatedCCWMirrored,
+	}
+
+	// Define supported formats
+	formats := []string{"jpg", "png", "tiff", "webp"}
+
+	// Generate test cases for all combinations
+	var testCases []struct {
+		name                string
+		fileName            string
+		expectedOrientation int
+	}
+
+	for prefix, orientation := range orientations {
+		for _, format := range formats {
+			testCases = append(testCases, struct {
+				name                string
+				fileName            string
+				expectedOrientation int
+			}{
+				name:                fmt.Sprintf("%s (%s)", prefix, format),
+				fileName:            fmt.Sprintf("%s.%s", prefix, format),
+				expectedOrientation: orientation,
+			})
+		}
+	}
+
+	dec, err := NewDecoder(DecoderOptions{})
+	require.NoError(t, err)
+
+	for _, tc := range testCases {
+		var orientation int
+		imgPath := filepath.Join(imgDir, tc.fileName)
+		file, err := os.Open(imgPath)
+		require.NoError(t, err)
+		defer file.Close()
+
+		_, format, err := dec.DecodeConfig(file)
+		require.NoError(t, err)
+
+		t.Run(tc.name+"_file", func(t *testing.T) {
+			_, err = file.Seek(0, io.SeekStart)
+			require.NoError(t, err)
+
+			orientation, err = GetImageOrientation(file, format)
+			require.NoError(t, err)
+			require.Equal(t, tc.expectedOrientation, orientation, "Incorrect orientation detected for %s", tc.fileName)
+		})
+
+		t.Run(tc.name+"_reader", func(t *testing.T) {
+			_, err = file.Seek(0, io.SeekStart)
+			require.NoError(t, err)
+
+			orientation, err = GetImageOrientation(&io.LimitedReader{R: file, N: 1024 * 1024}, format)
+			require.NoError(t, err)
+			require.Equal(t, tc.expectedOrientation, orientation, "Incorrect orientation detected for %s", tc.fileName)
+		})
+	}
+}
diff --git a/server/channels/app/plugin_api.go b/server/channels/app/plugin_api.go
index 7d903bd446..c07f897669 100644
--- a/server/channels/app/plugin_api.go
+++ b/server/channels/app/plugin_api.go
@@ -948,7 +948,7 @@ func (api *PluginAPI) SetTeamIcon(teamID string, data []byte) *model.AppError {
 		return err
 	}
 
-	return api.app.SetTeamIconFromFile(team, bytes.NewReader(data))
+	return api.app.SetTeamIconFromFile(api.ctx, team, bytes.NewReader(data))
 }
 
 func (api *PluginAPI) OpenInteractiveDialog(dialog model.OpenDialogRequest) *model.AppError {
@@ -1103,12 +1103,15 @@ func (api *PluginAPI) UpdateUserRoles(userID string, newRoles string) (*model.Us
 func (api *PluginAPI) LogDebug(msg string, keyValuePairs ...any) {
 	api.logger.Debugw(msg, keyValuePairs...)
 }
+
 func (api *PluginAPI) LogInfo(msg string, keyValuePairs ...any) {
 	api.logger.Infow(msg, keyValuePairs...)
 }
+
 func (api *PluginAPI) LogError(msg string, keyValuePairs ...any) {
 	api.logger.Errorw(msg, keyValuePairs...)
 }
+
 func (api *PluginAPI) LogWarn(msg string, keyValuePairs ...any) {
 	api.logger.Warnw(msg, keyValuePairs...)
 }
@@ -1320,7 +1323,8 @@ func (api *PluginAPI) DeleteOAuthApp(appID string) *model.AppError {
 // PublishPluginClusterEvent broadcasts a plugin event to all other running instances of
 // the calling plugin.
 func (api *PluginAPI) PublishPluginClusterEvent(ev model.PluginClusterEvent,
-	opts model.PluginClusterEventSendOptions) error {
+	opts model.PluginClusterEventSendOptions,
+) error {
 	if api.app.Cluster() == nil {
 		return nil
 	}
diff --git a/server/channels/app/plugin_api_test.go b/server/channels/app/plugin_api_test.go
index 9a543b4f45..4cde27ce87 100644
--- a/server/channels/app/plugin_api_test.go
+++ b/server/channels/app/plugin_api_test.go
@@ -1177,7 +1177,7 @@ func TestPluginAPIGetTeamIcon(t *testing.T) {
 	fileReader := bytes.NewReader(dataBytes)
 
 	// Set the Team Icon
-	appErr := th.App.SetTeamIconFromFile(th.BasicTeam, fileReader)
+	appErr := th.App.SetTeamIconFromFile(th.Context, th.BasicTeam, fileReader)
 	require.Nil(t, appErr)
 
 	// Get the team icon to check
@@ -1239,7 +1239,7 @@ func TestPluginAPIRemoveTeamIcon(t *testing.T) {
 	fileReader := bytes.NewReader(dataBytes)
 
 	// Set the Team Icon
-	err := th.App.SetTeamIconFromFile(th.BasicTeam, fileReader)
+	err := th.App.SetTeamIconFromFile(th.Context, th.BasicTeam, fileReader)
 	require.Nil(t, err)
 	err = api.RemoveTeamIcon(th.BasicTeam.Id)
 	require.Nil(t, err)
diff --git a/server/channels/app/post_metadata.go b/server/channels/app/post_metadata.go
index 1079ec1bbd..3a5decbccd 100644
--- a/server/channels/app/post_metadata.go
+++ b/server/channels/app/post_metadata.go
@@ -650,7 +650,6 @@ func (a *App) getLinkMetadata(c request.CTX, requestURL string, timestamp int64,
 	var err error
 	if looksLikeAPermalink(requestURL, a.GetSiteURL()) && *a.Config().ServiceSettings.EnablePermalinkPreviews {
 		permalink, err = a.getLinkMetadataForPermalink(c, requestURL)
-
 		if err != nil {
 			return nil, nil, nil, err
 		}
@@ -784,7 +783,7 @@ func (a *App) getLinkMetadataForURL(c request.CTX, requestURL string) (*opengrap
 
 	if err == nil {
 		// Parse the data
-		og, image, err = a.parseLinkMetadata(requestURL, body, contentType)
+		og, image, err = a.parseLinkMetadata(c, requestURL, body, contentType)
 	}
 	og = model.TruncateOpenGraph(og) // remove unwanted length of texts
 
@@ -878,7 +877,7 @@ func peekContentType(p *bufio.Reader) string {
 	return http.DetectContentType(byt)
 }
 
-func (a *App) parseLinkMetadata(requestURL string, body io.Reader, contentType string) (*opengraph.OpenGraph, *model.PostImage, error) {
+func (a *App) parseLinkMetadata(rctx request.CTX, requestURL string, body io.Reader, contentType string) (*opengraph.OpenGraph, *model.PostImage, error) {
 	if contentType == "" {
 		bufRd := bufio.NewReader(body)
 		// If the content-type is missing we try to detect it from the actual data.
@@ -893,7 +892,7 @@ func (a *App) parseLinkMetadata(requestURL string, body io.Reader, contentType s
 
 		return nil, image, nil
 	} else if strings.HasPrefix(contentType, "image") {
-		image, err := parseImages(io.LimitReader(body, MaxMetadataImageSize))
+		image, err := parseImages(rctx, requestURL, io.LimitReader(body, MaxMetadataImageSize))
 		return nil, image, err
 	} else if strings.HasPrefix(contentType, "text/html") {
 		og := a.parseOpenGraphMetadata(requestURL, body, contentType)
@@ -909,7 +908,7 @@ func (a *App) parseLinkMetadata(requestURL string, body io.Reader, contentType s
 	return nil, nil, nil
 }
 
-func parseImages(body io.Reader) (*model.PostImage, error) {
+func parseImages(rctx request.CTX, requestURL string, body io.Reader) (*model.PostImage, error) {
 	// Store any data that is read for the config for any further processing
 	buf := &bytes.Buffer{}
 	t := io.TeeReader(body, buf)
@@ -927,12 +926,14 @@ func parseImages(body io.Reader) (*model.PostImage, error) {
 	}
 
 	if format == "jpeg" {
-		if imageOrientation, err := imaging.GetImageOrientation(io.MultiReader(buf, body)); err == nil &&
+		if imageOrientation, err := imaging.GetImageOrientation(io.MultiReader(buf, body), format); err == nil &&
 			(imageOrientation == imaging.RotatedCWMirrored ||
 				imageOrientation == imaging.RotatedCCW ||
 				imageOrientation == imaging.RotatedCCWMirrored ||
 				imageOrientation == imaging.RotatedCW) {
 			image.Width, image.Height = image.Height, image.Width
+		} else if err != nil {
+			rctx.Logger().Warn("Failed to get image orientation", mlog.Err(err), mlog.String("request_url", requestURL))
 		}
 	}
 
diff --git a/server/channels/app/post_metadata_test.go b/server/channels/app/post_metadata_test.go
index 081bd24280..da86ee7ca5 100644
--- a/server/channels/app/post_metadata_test.go
+++ b/server/channels/app/post_metadata_test.go
@@ -29,6 +29,8 @@ import (
 
 	"github.com/mattermost/mattermost/server/public/model"
 	"github.com/mattermost/mattermost/server/public/shared/httpservice"
+	"github.com/mattermost/mattermost/server/public/shared/mlog"
+	"github.com/mattermost/mattermost/server/public/shared/request"
 	"github.com/mattermost/mattermost/server/v8/channels/app/platform"
 	"github.com/mattermost/mattermost/server/v8/channels/utils/testutils"
 	"github.com/mattermost/mattermost/server/v8/platform/services/imageproxy"
@@ -2673,7 +2675,7 @@ func TestParseLinkMetadata(t *testing.T) {
 	}
 
 	t.Run("image", func(t *testing.T) {
-		og, dimensions, err := th.App.parseLinkMetadata(imageURL, makeImageReader(), "image/png")
+		og, dimensions, err := th.App.parseLinkMetadata(th.Context, imageURL, makeImageReader(), "image/png")
 		assert.NoError(t, err)
 
 		assert.Nil(t, og)
@@ -2685,7 +2687,7 @@ func TestParseLinkMetadata(t *testing.T) {
 	})
 
 	t.Run("image with no content-type given", func(t *testing.T) {
-		og, dimensions, err := th.App.parseLinkMetadata(imageURL, makeImageReader(), "")
+		og, dimensions, err := th.App.parseLinkMetadata(th.Context, imageURL, makeImageReader(), "")
 		assert.NoError(t, err)
 
 		assert.Nil(t, og)
@@ -2697,7 +2699,7 @@ func TestParseLinkMetadata(t *testing.T) {
 	})
 
 	t.Run("malformed image", func(t *testing.T) {
-		og, dimensions, err := th.App.parseLinkMetadata(imageURL, makeOpenGraphReader(), "image/png")
+		og, dimensions, err := th.App.parseLinkMetadata(th.Context, imageURL, makeOpenGraphReader(), "image/png")
 		assert.Error(t, err)
 
 		assert.Nil(t, og)
@@ -2705,7 +2707,7 @@ func TestParseLinkMetadata(t *testing.T) {
 	})
 
 	t.Run("opengraph", func(t *testing.T) {
-		og, dimensions, err := th.App.parseLinkMetadata(ogURL, makeOpenGraphReader(), "text/html; charset=utf-8")
+		og, dimensions, err := th.App.parseLinkMetadata(th.Context, ogURL, makeOpenGraphReader(), "text/html; charset=utf-8")
 		assert.NoError(t, err)
 
 		assert.NotNil(t, og)
@@ -2716,7 +2718,7 @@ func TestParseLinkMetadata(t *testing.T) {
 	})
 
 	t.Run("malformed opengraph", func(t *testing.T) {
-		og, dimensions, err := th.App.parseLinkMetadata(ogURL, makeImageReader(), "text/html; charset=utf-8")
+		og, dimensions, err := th.App.parseLinkMetadata(th.Context, ogURL, makeImageReader(), "text/html; charset=utf-8")
 		assert.NoError(t, err)
 
 		assert.Nil(t, og)
@@ -2724,7 +2726,7 @@ func TestParseLinkMetadata(t *testing.T) {
 	})
 
 	t.Run("neither", func(t *testing.T) {
-		og, dimensions, err := th.App.parseLinkMetadata("http://example.com/test.wad", strings.NewReader("garbage"), "application/x-doom")
+		og, dimensions, err := th.App.parseLinkMetadata(th.Context, "http://example.com/test.wad", strings.NewReader("garbage"), "application/x-doom")
 		assert.NoError(t, err)
 
 		assert.Nil(t, og)
@@ -2732,7 +2734,7 @@ func TestParseLinkMetadata(t *testing.T) {
 	})
 
 	t.Run("svg", func(t *testing.T) {
-		og, dimensions, err := th.App.parseLinkMetadata("http://example.com/image.svg", nil, "image/svg+xml")
+		og, dimensions, err := th.App.parseLinkMetadata(th.Context, "http://example.com/image.svg", nil, "image/svg+xml")
 		assert.NoError(t, err)
 
 		assert.Nil(t, og)
@@ -2820,6 +2822,14 @@ func TestParseImages(t *testing.T) {
 				Format: "jpeg",
 			},
 		},
+		"jpg-9": {
+			FileName: "orientation_test_9.jpeg",
+			Expected: &model.PostImage{
+				Width:  4000,
+				Height: 2667,
+				Format: "jpeg",
+			},
+		},
 		"animated gif": {
 			FileName: "testgif.gif",
 			Expected: &model.PostImage{
@@ -2842,7 +2852,7 @@ func TestParseImages(t *testing.T) {
 			file, err := testutils.ReadTestFile(testCase.FileName)
 			require.NoError(t, err)
 
-			result, err := parseImages(bytes.NewReader(file))
+			result, err := parseImages(request.EmptyContext(mlog.CreateConsoleTestLogger(t)), "", bytes.NewReader(file))
 			if testCase.ExpectError {
 				assert.Error(t, err)
 			} else {
diff --git a/server/channels/app/team.go b/server/channels/app/team.go
index ebaa2b5bce..17f90f9dcb 100644
--- a/server/channels/app/team.go
+++ b/server/channels/app/team.go
@@ -1944,16 +1944,16 @@ func (a *App) GetTeamIcon(team *model.Team) ([]byte, *model.AppError) {
 	return data, nil
 }
 
-func (a *App) SetTeamIcon(teamID string, imageData *multipart.FileHeader) *model.AppError {
+func (a *App) SetTeamIcon(rctx request.CTX, teamID string, imageData *multipart.FileHeader) *model.AppError {
 	file, err := imageData.Open()
 	if err != nil {
 		return model.NewAppError("SetTeamIcon", "api.team.set_team_icon.open.app_error", nil, "", http.StatusBadRequest).Wrap(err)
 	}
 	defer file.Close()
-	return a.SetTeamIconFromMultiPartFile(teamID, file)
+	return a.SetTeamIconFromMultiPartFile(rctx, teamID, file)
 }
 
-func (a *App) SetTeamIconFromMultiPartFile(teamID string, file multipart.File) *model.AppError {
+func (a *App) SetTeamIconFromMultiPartFile(rctx request.CTX, teamID string, file multipart.File) *model.AppError {
 	team, getTeamErr := a.GetTeam(teamID)
 
 	if getTeamErr != nil {
@@ -1969,17 +1969,21 @@ func (a *App) SetTeamIconFromMultiPartFile(teamID string, file multipart.File) *
 			nil, "", http.StatusBadRequest).Wrap(limitErr)
 	}
 
-	return a.SetTeamIconFromFile(team, file)
+	return a.SetTeamIconFromFile(rctx, team, file)
 }
 
-func (a *App) SetTeamIconFromFile(team *model.Team, file io.Reader) *model.AppError {
+func (a *App) SetTeamIconFromFile(rctx request.CTX, team *model.Team, file io.ReadSeeker) *model.AppError {
 	// Decode image into Image object
-	img, _, err := image.Decode(file)
+	img, format, err := image.Decode(file)
 	if err != nil {
 		return model.NewAppError("SetTeamIcon", "api.team.set_team_icon.decode.app_error", nil, "", http.StatusBadRequest).Wrap(err)
 	}
 
-	orientation, _ := imaging.GetImageOrientation(file)
+	orientation, err := imaging.GetImageOrientation(file, format)
+	if err != nil {
+		rctx.Logger().Warn("Failed to get image orientation", mlog.Err(err))
+	}
+
 	img = imaging.MakeImageUpright(img, orientation)
 
 	// Scale team icon
diff --git a/server/channels/app/user.go b/server/channels/app/user.go
index e20d5fb420..02f1cff093 100644
--- a/server/channels/app/user.go
+++ b/server/channels/app/user.go
@@ -882,14 +882,18 @@ func (a *App) SetProfileImageFromMultiPartFile(c request.CTX, userID string, fil
 	return a.SetProfileImageFromFile(c, userID, file)
 }
 
-func (a *App) AdjustImage(file io.Reader) (*bytes.Buffer, *model.AppError) {
+func (a *App) AdjustImage(rctx request.CTX, file io.ReadSeeker) (*bytes.Buffer, *model.AppError) {
 	// Decode image into Image object
-	img, _, err := a.ch.imgDecoder.Decode(file)
+	img, format, err := a.ch.imgDecoder.Decode(file)
 	if err != nil {
 		return nil, model.NewAppError("SetProfileImage", "api.user.upload_profile_user.decode.app_error", nil, "", http.StatusBadRequest).Wrap(err)
 	}
 
-	orientation, _ := imaging.GetImageOrientation(file)
+	orientation, err := imaging.GetImageOrientation(file, format)
+	if err != nil {
+		rctx.Logger().Warn("Failed to get image orientation", mlog.Err(err))
+	}
+
 	img = imaging.MakeImageUpright(img, orientation)
 
 	// Scale profile image
@@ -904,8 +908,8 @@ func (a *App) AdjustImage(file io.Reader) (*bytes.Buffer, *model.AppError) {
 	return buf, nil
 }
 
-func (a *App) SetProfileImageFromFile(c request.CTX, userID string, file io.Reader) *model.AppError {
-	buf, err := a.AdjustImage(file)
+func (a *App) SetProfileImageFromFile(c request.CTX, userID string, file io.ReadSeeker) *model.AppError {
+	buf, err := a.AdjustImage(c, file)
 	if err != nil {
 		return err
 	}
@@ -1363,7 +1367,6 @@ func (a *App) UpdateUser(c request.CTX, user *model.User, sendNotifications bool
 
 func (a *App) UpdateUserActive(c request.CTX, userID string, active bool) *model.AppError {
 	user, err := a.GetUser(userID)
-
 	if err != nil {
 		return err
 	}
@@ -1671,7 +1674,6 @@ func (a *App) GetPasswordRecoveryToken(token string) (*model.Token, *model.AppEr
 
 func (a *App) GetTokenById(token string) (*model.Token, *model.AppError) {
 	rtoken, err := a.Srv().Store().Token().GetByToken(token)
-
 	if err != nil {
 		var status int
 
@@ -2043,7 +2045,6 @@ func (a *App) VerifyUserEmail(userID, email string) *model.AppError {
 	a.InvalidateCacheForUser(userID)
 
 	user, err := a.GetUser(userID)
-
 	if err != nil {
 		return err
 	}
@@ -2788,7 +2789,6 @@ func (a *App) UpdateThreadFollowForUserFromChannelAdd(c request.CTX, userID, tea
 
 	message := model.NewWebSocketEvent(model.WebsocketEventThreadUpdated, teamID, "", userID, nil, "")
 	userThread, err := a.Srv().Store().Thread().GetThreadForUser(tm, true, a.IsPostPriorityEnabled())
-
 	if err != nil {
 		var errNotFound *store.ErrNotFound
 		if errors.As(err, &errNotFound) {
diff --git a/server/channels/app/user_test.go b/server/channels/app/user_test.go
index c0b668ff4d..15a93de5bd 100644
--- a/server/channels/app/user_test.go
+++ b/server/channels/app/user_test.go
@@ -112,14 +112,14 @@ func TestAdjustProfileImage(t *testing.T) {
 	th := Setup(t).InitBasic()
 	defer th.TearDown()
 
-	_, appErr := th.App.AdjustImage(bytes.NewReader([]byte{}))
+	_, appErr := th.App.AdjustImage(th.Context, bytes.NewReader([]byte{}))
 	require.NotNil(t, appErr)
 
 	// test image isn't the correct dimensions
 	// it should be adjusted
 	testjpg, err := testutils.ReadTestFile("testjpg.jpg")
 	require.NoError(t, err)
-	adjusted, appErr := th.App.AdjustImage(bytes.NewReader(testjpg))
+	adjusted, appErr := th.App.AdjustImage(th.Context, bytes.NewReader(testjpg))
 	require.Nil(t, appErr)
 	assert.True(t, adjusted.Len() > 0)
 	assert.NotEqual(t, testjpg, adjusted)
@@ -128,7 +128,7 @@ func TestAdjustProfileImage(t *testing.T) {
 	user := th.BasicUser
 	image, appErr := th.App.GetDefaultProfileImage(user)
 	require.Nil(t, appErr)
-	image2, appErr := th.App.AdjustImage(bytes.NewReader(image))
+	image2, appErr := th.App.AdjustImage(th.Context, bytes.NewReader(image))
 	require.Nil(t, appErr)
 	assert.Equal(t, image, image2.Bytes())
 }
@@ -317,7 +317,8 @@ func TestCreateUser(t *testing.T) {
 			func main() {
 				plugin.ClientMain(&MyPlugin{})
 			}
-		`}, th.App, th.NewPluginAPI)
+		`,
+			}, th.App, th.NewPluginAPI)
 		defer tearDown()
 
 		user := &model.User{
@@ -1924,7 +1925,7 @@ func TestUpdateUserRolesWithUser(t *testing.T) {
 	_, err = th.App.UpdateUserRolesWithUser(th.Context, user, "does not exist", false)
 	require.NotNil(t, err)
 
-	//Test reset to User role
+	// Test reset to User role
 	user, err = th.App.UpdateUserRolesWithUser(th.Context, user, model.SystemUserRoleId, false)
 	require.Nil(t, err)
 	assert.Equal(t, user.Roles, model.SystemUserRoleId)
diff --git a/server/go.mod b/server/go.mod
index 1227745700..a522f088ac 100644
--- a/server/go.mod
+++ b/server/go.mod
@@ -10,6 +10,7 @@ require (
 	github.com/anthonynsimon/bild v0.14.0
 	github.com/avct/uasurfer v0.0.0-20240501094946-ca0c4d1e541b
 	github.com/aws/aws-sdk-go v1.55.6
+	github.com/bep/imagemeta v0.10.0
 	github.com/blang/semver/v4 v4.0.0
 	github.com/blevesearch/bleve/v2 v2.4.4-0.20250115090822-cbafdca08538
 	github.com/cespare/xxhash/v2 v2.3.0
@@ -59,7 +60,6 @@ require (
 	github.com/reflog/dateconstraints v0.2.1
 	github.com/rs/cors v1.11.1
 	github.com/rudderlabs/analytics-go v3.3.3+incompatible
-	github.com/rwcarlsen/goexif v0.0.0-20190401172101-9e8deecbddbd
 	github.com/sirupsen/logrus v1.9.3
 	github.com/spf13/cobra v1.8.1
 	github.com/spf13/viper v1.19.0
@@ -75,7 +75,7 @@ require (
 	golang.org/x/crypto v0.32.0
 	golang.org/x/image v0.23.0
 	golang.org/x/net v0.34.0
-	golang.org/x/sync v0.10.0
+	golang.org/x/sync v0.12.0
 	golang.org/x/term v0.28.0
 	gopkg.in/mail.v2 v2.3.1
 	gopkg.in/yaml.v3 v3.0.1
@@ -222,7 +222,7 @@ require (
 	golang.org/x/exp v0.0.0-20250106191152-7588d65b2ba8 // indirect
 	golang.org/x/mod v0.22.0 // indirect
 	golang.org/x/sys v0.29.0 // indirect
-	golang.org/x/text v0.21.0 // indirect
+	golang.org/x/text v0.23.0 // indirect
 	golang.org/x/tools v0.29.0 // indirect
 	google.golang.org/genproto/googleapis/rpc v0.0.0-20250124145028-65684f501c47 // indirect
 	google.golang.org/grpc v1.70.0 // indirect
diff --git a/server/go.sum b/server/go.sum
index c48c6533b6..933697bc2f 100644
--- a/server/go.sum
+++ b/server/go.sum
@@ -56,6 +56,8 @@ github.com/beorn7/perks v0.0.0-20180321164747-3a771d992973/go.mod h1:Dwedo/Wpr24
 github.com/beorn7/perks v1.0.0/go.mod h1:KWe93zE9D1o94FZ5RNwFwVgaQK1VOXiVxmqh+CedLV8=
 github.com/beorn7/perks v1.0.1 h1:VlbKKnNfV8bJzeqoa4cOKqO6bYr3WgKZxO8Z16+hsOM=
 github.com/beorn7/perks v1.0.1/go.mod h1:G2ZrVWU2WbWT9wwq4/hrbKbnv/1ERSJQ0ibhJ6rlkpw=
+github.com/bep/imagemeta v0.10.0 h1:kbQxe8SLHTUEEOT/DvLMGslIJy9Z1R+ZAckkIUnUBw4=
+github.com/bep/imagemeta v0.10.0/go.mod h1:23AF6O+4fUi9avjiydpKLStUNtJr5hJB4rarG18JpN8=
 github.com/bits-and-blooms/bitset v1.10.0/go.mod h1:7hO7Gc7Pp1vODcmWvKMRA9BNmbv6a/7QIWpPxHddWR8=
 github.com/bits-and-blooms/bitset v1.12.0/go.mod h1:7hO7Gc7Pp1vODcmWvKMRA9BNmbv6a/7QIWpPxHddWR8=
 github.com/bits-and-blooms/bitset v1.20.0 h1:2F+rfL86jE2d/bmw7OhqUg2Sj/1rURkBn3MdfoPyRVU=
@@ -758,8 +760,9 @@ golang.org/x/sync v0.1.0/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
 golang.org/x/sync v0.3.0/go.mod h1:FU7BRWz2tNW+3quACPkgCx/L+uEAv1htQ0V83Z9Rj+Y=
 golang.org/x/sync v0.6.0/go.mod h1:Czt+wKu1gCyEFDUtn0jG5QVvpJ6rzVqr5aXyt9drQfk=
 golang.org/x/sync v0.7.0/go.mod h1:Czt+wKu1gCyEFDUtn0jG5QVvpJ6rzVqr5aXyt9drQfk=
-golang.org/x/sync v0.10.0 h1:3NQrjDixjgGwUOCaF8w2+VYHv0Ve/vGYSbdkTa98gmQ=
 golang.org/x/sync v0.10.0/go.mod h1:Czt+wKu1gCyEFDUtn0jG5QVvpJ6rzVqr5aXyt9drQfk=
+golang.org/x/sync v0.12.0 h1:MHc5BpPuC30uJk597Ri8TV3CNZcTLu6B6z4lJy+g6Jw=
+golang.org/x/sync v0.12.0/go.mod h1:1dzgHSNfp02xaA81J2MS99Qcpr2w7fw1gpm99rleRqA=
 golang.org/x/sys v0.0.0-20180830151530-49385e6e1522/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
 golang.org/x/sys v0.0.0-20180905080454-ebe1bf3edb33/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
 golang.org/x/sys v0.0.0-20180909124046-d0be0721c37e/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
@@ -821,8 +824,9 @@ golang.org/x/text v0.9.0/go.mod h1:e1OnstbJyHTd6l/uOt8jFFHp6TRDWZR/bV3emEE/zU8=
 golang.org/x/text v0.13.0/go.mod h1:TvPlkZtksWOMsz7fbANvkp4WM8x/WCo/om8BMLbz+aE=
 golang.org/x/text v0.14.0/go.mod h1:18ZOQIKpY8NJVqYksKHtTdi31H5itFRjB5/qKTNYzSU=
 golang.org/x/text v0.15.0/go.mod h1:18ZOQIKpY8NJVqYksKHtTdi31H5itFRjB5/qKTNYzSU=
-golang.org/x/text v0.21.0 h1:zyQAAkrwaneQ066sspRyJaG9VNi/YJ1NfzcGB3hZ/qo=
 golang.org/x/text v0.21.0/go.mod h1:4IBbMaMmOPCJ8SecivzSH54+73PCFmPWxNTLm+vZkEQ=
+golang.org/x/text v0.23.0 h1:D71I7dUrlY+VX0gQShAThNGHFxZ13dGLBHQLVl1mJlY=
+golang.org/x/text v0.23.0/go.mod h1:/BLNzu4aZCJ1+kcD0DNRotWKage4q2rGVAg4o22unh4=
 golang.org/x/time v0.0.0-20180412165947-fbb02b2291d2/go.mod h1:tRJNPiyCQ0inRvYxbN9jk5I+vvW/OXSQhTDSoE431IQ=
 golang.org/x/time v0.0.0-20181108054448-85acf8d2951c/go.mod h1:tRJNPiyCQ0inRvYxbN9jk5I+vvW/OXSQhTDSoE431IQ=
 golang.org/x/time v0.8.0 h1:9i3RxcPv3PZnitoVGMPDKZSq1xW1gK1Xy3ArNOGZfEg=
diff --git a/server/tests/exif_samples/down-mirrored.jpg b/server/tests/exif_samples/down-mirrored.jpg
new file mode 100644
index 0000000000..34a7b1d395
Binary files /dev/null and b/server/tests/exif_samples/down-mirrored.jpg differ
diff --git a/server/tests/exif_samples/down-mirrored.png b/server/tests/exif_samples/down-mirrored.png
new file mode 100644
index 0000000000..9d8a391766
Binary files /dev/null and b/server/tests/exif_samples/down-mirrored.png differ
diff --git a/server/tests/exif_samples/down-mirrored.tiff b/server/tests/exif_samples/down-mirrored.tiff
new file mode 100644
index 0000000000..5fdfcd7a19
Binary files /dev/null and b/server/tests/exif_samples/down-mirrored.tiff differ
diff --git a/server/tests/exif_samples/down-mirrored.webp b/server/tests/exif_samples/down-mirrored.webp
new file mode 100644
index 0000000000..30d49a249e
Binary files /dev/null and b/server/tests/exif_samples/down-mirrored.webp differ
diff --git a/server/tests/exif_samples/down.jpg b/server/tests/exif_samples/down.jpg
new file mode 100644
index 0000000000..9077a7c92b
Binary files /dev/null and b/server/tests/exif_samples/down.jpg differ
diff --git a/server/tests/exif_samples/down.png b/server/tests/exif_samples/down.png
new file mode 100644
index 0000000000..0b4df66f48
Binary files /dev/null and b/server/tests/exif_samples/down.png differ
diff --git a/server/tests/exif_samples/down.tiff b/server/tests/exif_samples/down.tiff
new file mode 100644
index 0000000000..a84e041c98
Binary files /dev/null and b/server/tests/exif_samples/down.tiff differ
diff --git a/server/tests/exif_samples/down.webp b/server/tests/exif_samples/down.webp
new file mode 100644
index 0000000000..0025aa9ad6
Binary files /dev/null and b/server/tests/exif_samples/down.webp differ
diff --git a/server/tests/exif_samples/left-mirrored.jpg b/server/tests/exif_samples/left-mirrored.jpg
new file mode 100644
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