diff --git a/NOTICE.txt b/NOTICE.txt
index 2263b006a4c..3f033ef65fd 100644
--- a/NOTICE.txt
+++ b/NOTICE.txt
@@ -7892,14 +7892,14 @@ THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR IMPLI
 
 ---
 
-## ledongthuc/pdf
+## mattermost/pdf
 
-This product contains 'ledongthuc/pdf' by Thuc Le.
+This product contains 'mattermost/pdf' by Mattermost, a fork of 'ledongthuc/pdf' by Thuc Le.
 
 PDF reader
 
 * HOMEPAGE:
-  * https://github.com/ledongthuc/pdf
+  * https://github.com/mattermost/pdf
 
 * LICENSE: BSD 3-Clause "New" or "Revised" License
 
diff --git a/server/channels/app/file.go b/server/channels/app/file.go
index 2d9ab8ff94b..761b5d91543 100644
--- a/server/channels/app/file.go
+++ b/server/channels/app/file.go
@@ -1767,6 +1767,7 @@ func (a *App) ExtractContentFromFileInfo(rctx request.CTX, fileInfo *model.FileI
 	// detached goroutine after Extract returns, so closing the file here would
 	// race with that goroutine still reading it.
 	text, err := docextractor.Extract(rctx.Logger(), fileInfo.Name, file, docextractor.ExtractSettings{
+		Ctx:              rctx.Context(),
 		ArchiveRecursion: *a.Config().FileSettings.ArchiveRecursion,
 		MaxFileSize:      *a.Config().FileSettings.MaxFileSize,
 		Timeout:          time.Duration(*a.Config().FileSettings.ExtractContentTimeout) * time.Second,
diff --git a/server/go.mod b/server/go.mod
index a36ef1d4c85..6efa9947b1d 100644
--- a/server/go.mod
+++ b/server/go.mod
@@ -42,7 +42,6 @@ require (
 	github.com/jaytaylor/html2text v0.0.0-20260303211410-1a4bdc82ecec
 	github.com/jmoiron/sqlx v1.4.0
 	github.com/klauspost/compress v1.18.6
-	github.com/ledongthuc/pdf v0.0.0-20250511090121-5959a4027728
 	github.com/lib/pq v1.12.3
 	github.com/mattermost/go-i18n v1.11.1-0.20211013152124-5c415071e404
 	github.com/mattermost/gosaml2 v0.10.0
@@ -51,6 +50,7 @@ require (
 	github.com/mattermost/mattermost-plugin-ai v1.14.0
 	github.com/mattermost/mattermost/server/public v0.4.0
 	github.com/mattermost/morph v1.1.0
+	github.com/mattermost/pdf v0.0.0-20260728101013-cd8a834041c4
 	github.com/mattermost/rsc v0.0.0-20160330161541-bbaefb05eaa0
 	github.com/mattermost/squirrel v0.5.0
 	github.com/mholt/archives v0.1.5
@@ -74,15 +74,15 @@ require (
 	github.com/tylerb/graceful v1.2.15
 	github.com/vmihailenco/msgpack/v5 v5.4.1
 	github.com/wiggin77/merror v1.0.5
-	github.com/wneessen/go-mail v0.7.3
+	github.com/wneessen/go-mail v0.8.1
 	github.com/xtgo/uuid v0.0.0-20140804021211-a0b114877d4c
 	github.com/yuin/goldmark v1.8.2
-	golang.org/x/crypto v0.53.0
+	golang.org/x/crypto v0.54.0
 	golang.org/x/image v0.44.0
 	golang.org/x/net v0.56.0
 	golang.org/x/sync v0.22.0
-	golang.org/x/sys v0.46.0
-	golang.org/x/term v0.44.0
+	golang.org/x/sys v0.47.0
+	golang.org/x/term v0.45.0
 	golang.org/x/text v0.40.0
 )
 
@@ -236,6 +236,3 @@ require (
 
 // See MM-66167, MM-68222 for more details.
 replace github.com/vmihailenco/msgpack/v5 => github.com/mattermost/msgpack/v5 v5.0.0-20260408165622-cadfad56a815
-
-// See MM-63434 for more details.
-replace github.com/ledongthuc/pdf => github.com/jgheithcock/pdf v0.0.0-20260404175814-28cd6530c1fe
diff --git a/server/go.sum b/server/go.sum
index 9c3e4bb9887..a35ec33a6fc 100644
--- a/server/go.sum
+++ b/server/go.sum
@@ -324,8 +324,6 @@ github.com/jaytaylor/html2text v0.0.0-20180606194806-57d518f124b0/go.mod h1:CVKl
 github.com/jaytaylor/html2text v0.0.0-20260303211410-1a4bdc82ecec h1:DrV+GDNKHeHyfqEZaoxQoHlWcgTBiaJ8ZUyNyd5vvkY=
 github.com/jaytaylor/html2text v0.0.0-20260303211410-1a4bdc82ecec/go.mod h1:CVKlgaMiht+LXvHG173ujK6JUhZXKb2u/BQtjPDIvyk=
 github.com/jellevandenhooff/dkim v0.0.0-20150330215556-f50fe3d243e1/go.mod h1:E0B/fFc00Y+Rasa88328GlI/XbtyysCtTHZS8h7IrBU=
-github.com/jgheithcock/pdf v0.0.0-20260404175814-28cd6530c1fe h1:9GAP+hdboArdSUwi82IXaNd+Qq8+cGFQh7xAcwZNN+s=
-github.com/jgheithcock/pdf v0.0.0-20260404175814-28cd6530c1fe/go.mod h1:1fEHWurg7pvf5SG6XNE5Q8UZmOwex51Mkx3SLhrW5B4=
 github.com/jhump/protoreflect v1.17.0 h1:qOEr613fac2lOuTgWN4tPAtLL7fUSbuJL5X5XumQh94=
 github.com/jhump/protoreflect v1.17.0/go.mod h1:h9+vUUL38jiBzck8ck+6G/aeMX8Z4QUY/NiJPwPNi+8=
 github.com/jmoiron/sqlx v1.4.0 h1:1PLqN7S1UYp5t4SrVVnt4nUVNemrDAtxlulVe+Qgm3o=
@@ -397,6 +395,8 @@ github.com/mattermost/morph v1.1.0 h1:Q9vrJbeM3s2jfweGheq12EFIzdNp9a/6IovcbvOQ6C
 github.com/mattermost/morph v1.1.0/go.mod h1:gD+EaqX2UMyyuzmF4PFh4r33XneQ8Nzi+0E8nXjMa3A=
 github.com/mattermost/msgpack/v5 v5.0.0-20260408165622-cadfad56a815 h1:uOi89NvrFmDngqMKjlLDxi+MNzJQLA3TqcU2p8czv34=
 github.com/mattermost/msgpack/v5 v5.0.0-20260408165622-cadfad56a815/go.mod h1:GaZTsDaehaPpQVyxrf5mtQlH+pc21PIudVV/E3rRQok=
+github.com/mattermost/pdf v0.0.0-20260728101013-cd8a834041c4 h1:iFMZLV6k/gOXuQmETk+Ym7FGn5nrBAKlQ0kY/FgK+ro=
+github.com/mattermost/pdf v0.0.0-20260728101013-cd8a834041c4/go.mod h1:pNks5J7leEpCnswIJaGfqiz/MQ0lExHgKl+A53aEXrg=
 github.com/mattermost/rsc v0.0.0-20160330161541-bbaefb05eaa0 h1:G9tL6JXRBMzjuD1kkBtcnd42kUiT6QDwxfFYu7adM6o=
 github.com/mattermost/rsc v0.0.0-20160330161541-bbaefb05eaa0/go.mod h1:nV5bfVpT//+B1RPD2JvRnxbkLmJEYXmRaaVl15fsXjs=
 github.com/mattermost/squirrel v0.5.0 h1:81QPS0aA+inQbpA7Pzmv6O9sWwB6VaBh/VYw3oJf8ZY=
@@ -660,8 +660,8 @@ github.com/wiggin77/merror v1.0.5 h1:P+lzicsn4vPMycAf2mFf7Zk6G9eco5N+jB1qJ2XW3ME
 github.com/wiggin77/merror v1.0.5/go.mod h1:H2ETSu7/bPE0Ymf4bEwdUoo73OOEkdClnoRisfw0Nm0=
 github.com/wiggin77/srslog v1.0.1 h1:gA2XjSMy3DrRdX9UqLuDtuVAAshb8bE1NhX1YK0Qe+8=
 github.com/wiggin77/srslog v1.0.1/go.mod h1:fehkyYDq1QfuYn60TDPu9YdY2bB85VUW2mvN1WynEls=
-github.com/wneessen/go-mail v0.7.3 h1:g3DravXC5SMlVdboFrQA8Jx95A8sOzoBeS5F+vzNRK0=
-github.com/wneessen/go-mail v0.7.3/go.mod h1:QGhBX0yNbc1J+Mkjcu7z2rpj4B4l+BmDY8gYznPC9sk=
+github.com/wneessen/go-mail v0.8.1 h1:tVcncj02/QySVFw3zr/kXOzZcuFQqBNT6K+Rbgm/pcM=
+github.com/wneessen/go-mail v0.8.1/go.mod h1:dWZ61zadzCIyvB4y1/YzC5O7MrbbzBfPkARmbosdf8w=
 github.com/xtgo/uuid v0.0.0-20140804021211-a0b114877d4c h1:3lbZUMbMiGUW/LMkfsEABsc5zNT9+b1CvsJx47JzJ8g=
 github.com/xtgo/uuid v0.0.0-20140804021211-a0b114877d4c/go.mod h1:UrdRz5enIKZ63MEE3IF9l2/ebyx59GyGgPi+tICQdmM=
 github.com/xyproto/randomstring v1.0.5 h1:YtlWPoRdgMu3NZtP45drfy1GKoojuR7hmRcnhZqKjWU=
@@ -711,8 +711,8 @@ golang.org/x/crypto v0.14.0/go.mod h1:MVFd36DqK4CsrnJYDkBA3VC4m2GkXAM0PvzMCn4JQf
 golang.org/x/crypto v0.19.0/go.mod h1:Iy9bg/ha4yyC70EfRS8jz+B6ybOBKMaSxLj6P6oBDfU=
 golang.org/x/crypto v0.23.0/go.mod h1:CKFgDieR+mRhux2Lsu27y0fO304Db0wZe70UKqHu0v8=
 golang.org/x/crypto v0.31.0/go.mod h1:kDsLvtWBEx7MV9tJOj9bnXsPbxwJQ6csT/x4KIN4Ssk=
-golang.org/x/crypto v0.53.0 h1:QZ4Muo8THX6CizN2vPPd5fBGHyogrdK9fG4wLPFUsto=
-golang.org/x/crypto v0.53.0/go.mod h1:DNLU434OwVakk9PzuwV8w62mAJpRJL3vsgcfp4Qnsio=
+golang.org/x/crypto v0.54.0 h1:YLIA59K4fiNzHzjnZt2tUJQjQtUWfWbeHBqKtk3eScw=
+golang.org/x/crypto v0.54.0/go.mod h1:KWL8ny2AZdGR2cWmzeHrp2azQPGogOv+HeQaVEXC2dk=
 golang.org/x/exp v0.0.0-20190121172915-509febef88a4/go.mod h1:CJ0aWSM057203Lf6IL+f9T1iT9GByDxfZKAQTCR3kQA=
 golang.org/x/exp v0.0.0-20260508232706-74f9aab9d74a h1:+3jdDGGB8NGb1Zktc737jlt3/A5f6UlwSzmvqUuufxw=
 golang.org/x/exp v0.0.0-20260508232706-74f9aab9d74a/go.mod h1:d2fgXJLVs4dYDHUk5lwMIfzRzSrWCfGZb0ZqeLa/Vcw=
@@ -814,8 +814,8 @@ golang.org/x/sys v0.13.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.17.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/sys v0.20.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/sys v0.28.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
-golang.org/x/sys v0.46.0 h1:noSf2Fq6F8DBgS+LysIkx7rIExoNHJsxOAtPp4rthXw=
-golang.org/x/sys v0.46.0/go.mod h1:4GL1E5IUh+htKOUEOaiffhrAeqysfVGipDYzABqnCmw=
+golang.org/x/sys v0.47.0 h1:o7XGOvZQCADBQQ4Y7VNq2dRWQR7JmOUW8Kxx4ZsNgWs=
+golang.org/x/sys v0.47.0/go.mod h1:4GL1E5IUh+htKOUEOaiffhrAeqysfVGipDYzABqnCmw=
 golang.org/x/telemetry v0.0.0-20240228155512-f48c80bd79b2/go.mod h1:TeRTkGYfJXctD9OcfyVLyj2J3IxLnKwHJR8f4D8a3YE=
 golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1/go.mod h1:bj7SfCRtBDWHUb9snDiAeCFNEtKQo2Wmx5Cou7ajbmo=
 golang.org/x/term v0.0.0-20210927222741-03fcf44c2211/go.mod h1:jbD1KX2456YbFQfuXm/mYQcufACuNUgVhRMnK/tPxf8=
@@ -826,8 +826,8 @@ golang.org/x/term v0.13.0/go.mod h1:LTmsnFJwVN6bCy1rVCoS+qHT1HhALEFxKncY3WNNh4U=
 golang.org/x/term v0.17.0/go.mod h1:lLRBjIVuehSbZlaOtGMbcMncT+aqLLLmKrsjNrUguwk=
 golang.org/x/term v0.20.0/go.mod h1:8UkIAJTvZgivsXaD6/pH6U9ecQzZ45awqEOzuCvwpFY=
 golang.org/x/term v0.27.0/go.mod h1:iMsnZpn0cago0GOrHO2+Y7u7JPn5AylBrcoWkElMTSM=
-golang.org/x/term v0.44.0 h1:0rLvDRCtNj0gZkyIXhCyOb2OAzEhLVqc4B+hrsBhrmc=
-golang.org/x/term v0.44.0/go.mod h1:7ze4MdzUzLXpSAoFP1H0bOI9aXDqveSvatT5vKcFh2Y=
+golang.org/x/term v0.45.0 h1:NwWyBmoJCbfTHpxrWoZ9C6/VxOf7ic219I8xZZFdrf0=
+golang.org/x/term v0.45.0/go.mod h1:9aqxs0blBcrm/n0L9QW0aRVD+ktan8ssZromtqJC43w=
 golang.org/x/text v0.3.0/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
 golang.org/x/text v0.3.1-0.20180807135948-17ff2d5776d2/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
 golang.org/x/text v0.3.2/go.mod h1:bEr9sfX3Q8Zfm5fL9x+3itogRgK3+ptLWKqgva+5dAk=
diff --git a/server/platform/services/docextractor/archive.go b/server/platform/services/docextractor/archive.go
index 64309a2b3de..c66d3d65e28 100644
--- a/server/platform/services/docextractor/archive.go
+++ b/server/platform/services/docextractor/archive.go
@@ -6,6 +6,7 @@ package docextractor
 import (
 	"bytes"
 	"context"
+	"errors"
 	"fmt"
 	"io"
 	"io/fs"
@@ -40,7 +41,7 @@ func getExtAlsoTarGz(name string) string {
 	return filepath.Ext(name)
 }
 
-func (ae *archiveExtractor) Extract(name string, r io.ReadSeeker, maxFileSize int64) (string, error) {
+func (ae *archiveExtractor) Extract(ctx context.Context, name string, r io.ReadSeeker, maxFileSize int64) (string, error) {
 	// MM-65701: Skip 7zip files due to OOM vulnerability in bodgit/sevenzip library
 	match, _ := (archives.SevenZip{}).Match(context.Background(), name, r)
 	_, _ = r.Seek(0, io.SeekStart) // Reset reader position after Match reads from stream
@@ -102,9 +103,11 @@ func (ae *archiveExtractor) Extract(name string, r io.ReadSeeker, maxFileSize in
 				return fmt.Errorf("error reading archive entry %s: %w", path, err)
 			}
 
-			subtext, extractErr := ae.SubExtractor.Extract(filename, bytes.NewReader(data), maxFileSize)
+			subtext, extractErr := ae.SubExtractor.Extract(ctx, filename, bytes.NewReader(data), maxFileSize)
 			if extractErr == nil {
 				text.WriteString(subtext + " ")
+			} else if errors.Is(extractErr, context.Canceled) || errors.Is(extractErr, context.DeadlineExceeded) {
+				return fmt.Errorf("error extracting %q: %w", filename, extractErr)
 			}
 		}
 		return nil
diff --git a/server/platform/services/docextractor/archive_test.go b/server/platform/services/docextractor/archive_test.go
index 729f873a47a..b1eecb36c09 100644
--- a/server/platform/services/docextractor/archive_test.go
+++ b/server/platform/services/docextractor/archive_test.go
@@ -5,6 +5,7 @@ package docextractor
 
 import (
 	"bytes"
+	"context"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
@@ -17,7 +18,7 @@ func TestArchiveExtractorSkips7zip(t *testing.T) {
 	t.Run("7zip file with .7z extension returns empty string", func(t *testing.T) {
 		// Valid 7zip header (minimal)
 		sevenZipData := []byte{0x37, 0x7a, 0xbc, 0xaf, 0x27, 0x1c, 0x00, 0x00}
-		result, err := ae.Extract("test.7z", bytes.NewReader(sevenZipData), 0)
+		result, err := ae.Extract(context.Background(), "test.7z", bytes.NewReader(sevenZipData), 0)
 		require.NoError(t, err)
 		assert.Empty(t, result)
 	})
@@ -25,7 +26,7 @@ func TestArchiveExtractorSkips7zip(t *testing.T) {
 	t.Run("7zip content with wrong extension is still blocked", func(t *testing.T) {
 		// 7zip content disguised with .zip extension - should still be blocked via stream detection
 		sevenZipData := []byte{0x37, 0x7a, 0xbc, 0xaf, 0x27, 0x1c, 0x00, 0x00}
-		result, err := ae.Extract("malicious.zip", bytes.NewReader(sevenZipData), 0)
+		result, err := ae.Extract(context.Background(), "malicious.zip", bytes.NewReader(sevenZipData), 0)
 		require.NoError(t, err)
 		assert.Empty(t, result)
 	})
@@ -34,7 +35,7 @@ func TestArchiveExtractorSkips7zip(t *testing.T) {
 		junkPrefix := []byte{0x00, 0x00, 0x00, 0x00}
 		sevenZipSig := []byte{0x37, 0x7a, 0xbc, 0xaf, 0x27, 0x1c, 0x00, 0x00}
 		dataWithOffset := append(junkPrefix, sevenZipSig...)
-		result, err := ae.Extract("test.7z", bytes.NewReader(dataWithOffset), 0)
+		result, err := ae.Extract(context.Background(), "test.7z", bytes.NewReader(dataWithOffset), 0)
 		require.NoError(t, err)
 		assert.Empty(t, result)
 	})
@@ -46,7 +47,7 @@ func TestArchiveExtractorSkips7zip(t *testing.T) {
 		junkPrefix := []byte{0x00, 0x00, 0x00, 0x00}
 		sevenZipSig := []byte{0x37, 0x7a, 0xbc, 0xaf, 0x27, 0x1c, 0x00, 0x00}
 		dataWithOffset := append(junkPrefix, sevenZipSig...)
-		_, err := ae.Extract("malicious.zip", bytes.NewReader(dataWithOffset), 0)
+		_, err := ae.Extract(context.Background(), "malicious.zip", bytes.NewReader(dataWithOffset), 0)
 		assert.Error(t, err) // fails to extract as any valid archive format
 	})
 }
diff --git a/server/platform/services/docextractor/combine.go b/server/platform/services/docextractor/combine.go
index 277fe5772fe..6b0708d1304 100644
--- a/server/platform/services/docextractor/combine.go
+++ b/server/platform/services/docextractor/combine.go
@@ -4,6 +4,8 @@
 package docextractor
 
 import (
+	"context"
+	"errors"
 	"io"
 
 	"github.com/mattermost/mattermost/server/public/shared/mlog"
@@ -31,12 +33,17 @@ func (ce *combineExtractor) Match(filename string) bool {
 	return false
 }
 
-func (ce *combineExtractor) Extract(filename string, r io.ReadSeeker, maxFileSize int64) (string, error) {
+func (ce *combineExtractor) Extract(ctx context.Context, filename string, r io.ReadSeeker, maxFileSize int64) (string, error) {
 	for _, extractor := range ce.SubExtractors {
 		if extractor.Match(filename) {
 			r.Seek(0, io.SeekStart)
-			text, err := extractor.Extract(filename, r, maxFileSize)
+			text, err := extractor.Extract(ctx, filename, r, maxFileSize)
 			if err != nil {
+				// Context errors must not be retried: the caller explicitly
+				// cancelled or timed out, so stop immediately.
+				if errors.Is(err, context.Canceled) || errors.Is(err, context.DeadlineExceeded) {
+					return "", err
+				}
 				ce.logger.Warn("Unable to extract file content", mlog.String("file_name", filename), mlog.String("extractor", extractor.Name()), mlog.Err(err))
 				continue
 			}
diff --git a/server/platform/services/docextractor/docextractor.go b/server/platform/services/docextractor/docextractor.go
index 4e123decb4e..bdb1fe996e2 100644
--- a/server/platform/services/docextractor/docextractor.go
+++ b/server/platform/services/docextractor/docextractor.go
@@ -4,6 +4,8 @@
 package docextractor
 
 import (
+	"context"
+	"errors"
 	"fmt"
 	"io"
 	"time"
@@ -13,17 +15,21 @@ import (
 
 // ExtractSettings defines the features enabled/disable during the document text extraction.
 type ExtractSettings struct {
+	// Ctx is the parent context for the extraction. Cancellation propagates
+	// to context-aware extractors (e.g. the Go-native PDF extractor stops at
+	// the next page boundary). If nil, context.Background() is used.
+	Ctx              context.Context
 	ArchiveRecursion bool
 	MaxFileSize      int64
 	MMPreviewURL     string
 	MMPreviewSecret  string
-	// Timeout bounds how long a caller waits for a single extraction. A value
-	// <= 0 disables it. NOTE: this bounds wall-clock wait time, not CPU work.
-	// The docconv converters are not context-aware, so on timeout the
-	// converter keeps running to completion on a detached goroutine. A global
-	// cap on concurrent extractions (including those detached goroutines)
-	// prevents sustained uploads from accumulating unbounded docconv work.
-	// The per-extraction input bound is MaxFileSize.
+	// Timeout bounds how long a caller waits for a single extraction. When
+	// set, a child context with this deadline is derived from Ctx and passed
+	// to the extractor. Context-aware extractors (pdfExtractor) honour it
+	// and stop at the next page boundary; others run to completion on a
+	// detached goroutine but no longer hold the caller's worker slot. A
+	// global cap on concurrent extractions (including those detached
+	// goroutines) prevents sustained uploads from accumulating unbounded work.
 	Timeout time.Duration
 	// ReaderCloser, when set, transfers ownership of closing the input reader
 	// to this package. It is closed only after extraction has actually
@@ -73,13 +79,13 @@ func ExtractWithExtraExtractors(logger mlog.LoggerIFace, filename string, r io.R
 	return "", nil
 }
 
-// extractWithTimeout runs the extraction and stops waiting for it once
-// settings.Timeout elapses. Because the underlying docconv converters are not
-// context-aware, the extraction runs on a detached goroutine: on timeout we
-// stop waiting and return an error, releasing the caller (and its worker slot)
-// even though the converter keeps running. A global concurrency cap applies to
-// every in-flight extraction, including detached goroutines, so timed-out work
-// cannot accumulate beyond the limit.
+// extractWithTimeout runs the extraction under a context derived from
+// settings.Ctx. When settings.Timeout > 0 a deadline is added; on expiry the
+// caller is released and the extraction runs on a detached goroutine.
+// Context-aware extractors (pdfExtractor) honour cancellation at page
+// boundaries and stop promptly; others run to completion in the background.
+// A global concurrency cap applies to every in-flight extraction, including
+// detached goroutines, so timed-out work cannot accumulate beyond the limit.
 func extractWithTimeout(e Extractor, filename string, r io.ReadSeeker, settings ExtractSettings) (string, error) {
 	if !tryAcquireExtractionSlot() {
 		if settings.ReaderCloser != nil {
@@ -88,14 +94,22 @@ func extractWithTimeout(e Extractor, filename string, r io.ReadSeeker, settings
 		return "", fmt.Errorf("document text extraction capacity exhausted (%d concurrent extractions)", maxConcurrentExtractions)
 	}
 
+	ctx := settings.Ctx
+	if ctx == nil {
+		ctx = context.Background()
+	}
+
 	if settings.Timeout <= 0 {
 		defer releaseExtractionSlot()
 		if settings.ReaderCloser != nil {
 			defer settings.ReaderCloser.Close()
 		}
-		return e.Extract(filename, r, settings.MaxFileSize)
+		return e.Extract(ctx, filename, r, settings.MaxFileSize)
 	}
 
+	ctx, cancel := context.WithTimeout(ctx, settings.Timeout)
+	defer cancel()
+
 	type extractResult struct {
 		text string
 		err  error
@@ -119,17 +133,17 @@ func extractWithTimeout(e Extractor, filename string, r io.ReadSeeker, settings
 				resultCh <- extractResult{err: fmt.Errorf("panic during document text extraction: %v", rec)}
 			}
 		}()
-		text, err := e.Extract(filename, r, settings.MaxFileSize)
+		text, err := e.Extract(ctx, filename, r, settings.MaxFileSize)
 		resultCh <- extractResult{text: text, err: err}
 	}()
 
-	timer := time.NewTimer(settings.Timeout)
-	defer timer.Stop()
-
 	select {
 	case res := <-resultCh:
 		return res.text, res.err
-	case <-timer.C:
-		return "", fmt.Errorf("document text extraction timed out after %s", settings.Timeout)
+	case <-ctx.Done():
+		if errors.Is(ctx.Err(), context.DeadlineExceeded) {
+			return "", fmt.Errorf("document text extraction timed out after %s", settings.Timeout)
+		}
+		return "", fmt.Errorf("document text extraction cancelled: %w", ctx.Err())
 	}
 }
diff --git a/server/platform/services/docextractor/docextractor_test.go b/server/platform/services/docextractor/docextractor_test.go
index 66556ba2b29..67809914bbd 100644
--- a/server/platform/services/docextractor/docextractor_test.go
+++ b/server/platform/services/docextractor/docextractor_test.go
@@ -5,6 +5,7 @@ package docextractor
 
 import (
 	"bytes"
+	"context"
 	"errors"
 	"io"
 	"runtime"
@@ -175,7 +176,7 @@ func (te *customTestPdfExtractor) Match(filename string) bool {
 	return strings.HasSuffix(filename, ".pdf")
 }
 
-func (te *customTestPdfExtractor) Extract(filename string, r io.ReadSeeker, _ int64) (string, error) {
+func (te *customTestPdfExtractor) Extract(_ context.Context, filename string, r io.ReadSeeker, _ int64) (string, error) {
 	return "this is a text generated content", nil
 }
 
@@ -189,7 +190,7 @@ func (te *failingExtractor) Match(filename string) bool {
 	return true
 }
 
-func (te *failingExtractor) Extract(filename string, r io.ReadSeeker, _ int64) (string, error) {
+func (te *failingExtractor) Extract(_ context.Context, filename string, r io.ReadSeeker, _ int64) (string, error) {
 	return "", errors.New("this always fail")
 }
 
@@ -214,6 +215,44 @@ func TestExtractWithExtraExtractors(t *testing.T) {
 		assert.Contains(t, text, "document")
 		assert.Contains(t, text, "contains")
 	})
+
+	t.Run("cancelled context aborts extraction", func(t *testing.T) {
+		ctx, cancel := context.WithCancel(context.Background())
+		cancel()
+
+		text, err := ExtractWithExtraExtractors(
+			logger,
+			"file.txt",
+			bytes.NewReader([]byte("hello world")),
+			ExtractSettings{
+				Ctx:     ctx,
+				Timeout: time.Second,
+			},
+			[]Extractor{&slowExtractor{delay: 10 * time.Second}})
+		require.Error(t, err)
+		require.Empty(t, text)
+		require.Contains(t, err.Error(), "cancelled")
+	})
+
+	// Without context propagation a cancelled context would reach documentExtractor
+	// (which uses docconv and ignores the context), extract successfully, and return
+	// no error, silently swallowing the cancellation.
+	t.Run("cancelled context propagates through combineExtractor", func(t *testing.T) {
+		data, err := testutils.ReadTestFile("sample-doc.pdf")
+		require.NoError(t, err)
+
+		ctx, cancel := context.WithCancel(context.Background())
+		cancel()
+
+		// Inject pdfExtractor first so it runs before the system documentExtractor.
+		text, err := ExtractWithExtraExtractors(
+			logger,
+			"sample-doc.pdf",
+			bytes.NewReader(data),
+			ExtractSettings{Ctx: ctx}, []Extractor{&pdfExtractor{}})
+		require.ErrorIs(t, err, context.Canceled)
+		require.Empty(t, text)
+	})
 }
 
 type slowExtractor struct {
@@ -225,7 +264,7 @@ func (se *slowExtractor) Name() string { return "slowExtractor" }
 
 func (se *slowExtractor) Match(filename string) bool { return true }
 
-func (se *slowExtractor) Extract(filename string, r io.ReadSeeker, _ int64) (string, error) {
+func (se *slowExtractor) Extract(_ context.Context, filename string, r io.ReadSeeker, _ int64) (string, error) {
 	defer func() {
 		if se.done != nil {
 			close(se.done)
@@ -283,7 +322,7 @@ func (pe *panickingExtractor) Name() string { return "panickingExtractor" }
 
 func (pe *panickingExtractor) Match(filename string) bool { return true }
 
-func (pe *panickingExtractor) Extract(filename string, r io.ReadSeeker, _ int64) (string, error) {
+func (pe *panickingExtractor) Extract(_ context.Context, filename string, r io.ReadSeeker, _ int64) (string, error) {
 	panic("boom")
 }
 
@@ -308,7 +347,7 @@ func (be *blockingExtractor) Name() string { return "blockingExtractor" }
 
 func (be *blockingExtractor) Match(filename string) bool { return true }
 
-func (be *blockingExtractor) Extract(filename string, r io.ReadSeeker, _ int64) (string, error) {
+func (be *blockingExtractor) Extract(_ context.Context, filename string, r io.ReadSeeker, _ int64) (string, error) {
 	close(be.started)
 	<-be.release
 	if be.done != nil {
@@ -352,6 +391,45 @@ func TestExtractReaderCloserOwnership(t *testing.T) {
 	})
 }
 
+func TestExtractWithTimeout(t *testing.T) {
+	content, err := testutils.ReadTestFile("sample-doc.pdf")
+	require.NoError(t, err)
+
+	t.Run("no-timeout path propagates cancelled context", func(t *testing.T) {
+		ctx, cancel := context.WithCancel(context.Background())
+		cancel()
+
+		text, err := extractWithTimeout(
+			&pdfExtractor{},
+			"sample-doc.pdf",
+			bytes.NewReader(content),
+			ExtractSettings{Ctx: ctx})
+		require.ErrorIs(t, err, context.Canceled)
+		require.Empty(t, text)
+	})
+
+	// context.WithTimeout is derived from the (already cancelled) ExtractSettings.Ctx,
+	// so ctx.Done() fires immediately and the select returns a cancellation error
+	// before extraction can complete.
+	t.Run("goroutine/select path returns cancellation error", func(t *testing.T) {
+		ctx, cancel := context.WithCancel(context.Background())
+		cancel()
+
+		text, err := extractWithTimeout(&pdfExtractor{},
+			"sample-doc.pdf",
+			bytes.NewReader(content),
+			ExtractSettings{
+				Ctx:     ctx,
+				Timeout: time.Second,
+			})
+		require.Error(t, err)
+		require.Empty(t, text)
+		// Error comes from either the select's ctx.Done() branch ("cancelled") or
+		// directly from pdfExtractor propagating the cancelled context ("canceled").
+		require.Contains(t, strings.ToLower(err.Error()), "cancel")
+	})
+}
+
 func TestDocumentMaxFileSize(t *testing.T) {
 	logger := mlog.CreateConsoleTestLogger(t)
 
diff --git a/server/platform/services/docextractor/documents.go b/server/platform/services/docextractor/documents.go
index 7d2ad90fa26..bee71b6913d 100644
--- a/server/platform/services/docextractor/documents.go
+++ b/server/platform/services/docextractor/documents.go
@@ -4,6 +4,7 @@
 package docextractor
 
 import (
+	"context"
 	"errors"
 	"io"
 	"path"
@@ -38,7 +39,7 @@ func (de *documentExtractor) Match(filename string) bool {
 	return ok
 }
 
-func (de *documentExtractor) Extract(filename string, r io.ReadSeeker, maxFileSize int64) (out string, outErr error) {
+func (de *documentExtractor) Extract(_ context.Context, filename string, r io.ReadSeeker, maxFileSize int64) (out string, outErr error) {
 	defer func() {
 		if r := recover(); r != nil {
 			out = ""
diff --git a/server/platform/services/docextractor/interface.go b/server/platform/services/docextractor/interface.go
index 9bf55039177..d948f7d5cf2 100644
--- a/server/platform/services/docextractor/interface.go
+++ b/server/platform/services/docextractor/interface.go
@@ -4,12 +4,13 @@
 package docextractor
 
 import (
+	"context"
 	"io"
 )
 
 // Extractors define the interface needed to extract file content
 type Extractor interface {
 	Match(filename string) bool
-	Extract(filename string, file io.ReadSeeker, maxFileSize int64) (string, error)
+	Extract(ctx context.Context, filename string, file io.ReadSeeker, maxFileSize int64) (string, error)
 	Name() string
 }
diff --git a/server/platform/services/docextractor/mmpreview.go b/server/platform/services/docextractor/mmpreview.go
index 400cc495ff3..62f03b6e93e 100644
--- a/server/platform/services/docextractor/mmpreview.go
+++ b/server/platform/services/docextractor/mmpreview.go
@@ -9,6 +9,7 @@ package docextractor
 
 import (
 	"bytes"
+	"context"
 	"io"
 	"mime/multipart"
 	"net/http"
@@ -45,12 +46,12 @@ func (mpe *mmPreviewExtractor) Match(filename string) bool {
 	return mmpreviewSupportedExtensions[extension]
 }
 
-func (mpe *mmPreviewExtractor) Extract(filename string, file io.ReadSeeker, maxFileSize int64) (string, error) {
+func (mpe *mmPreviewExtractor) Extract(ctx context.Context, filename string, file io.ReadSeeker, maxFileSize int64) (string, error) {
 	b, w, err := createMultipartFormData("file", filename, file)
 	if err != nil {
 		return "", errors.Wrap(err, "Unable to generate file preview using mmpreview.")
 	}
-	req, err := http.NewRequest("POST", mpe.url+"/toPDF", &b)
+	req, err := http.NewRequestWithContext(ctx, "POST", mpe.url+"/toPDF", &b)
 	if err != nil {
 		return "", errors.Wrap(err, "Unable to generate file preview using mmpreview.")
 	}
@@ -70,7 +71,7 @@ func (mpe *mmPreviewExtractor) Extract(filename string, file io.ReadSeeker, maxF
 	if err != nil {
 		return "", errors.Wrap(err, "unable to read the response from mmpreview")
 	}
-	return mpe.pdfExtractor.Extract(filename, bytes.NewReader(data), maxFileSize)
+	return mpe.pdfExtractor.Extract(ctx, filename, bytes.NewReader(data), maxFileSize)
 }
 
 func createMultipartFormData(fieldName, fileName string, fileData io.ReadSeeker) (bytes.Buffer, *multipart.Writer, error) {
diff --git a/server/platform/services/docextractor/pdf.go b/server/platform/services/docextractor/pdf.go
index 67deb34bc9f..56167d939f7 100644
--- a/server/platform/services/docextractor/pdf.go
+++ b/server/platform/services/docextractor/pdf.go
@@ -5,6 +5,7 @@ package docextractor
 
 import (
 	"bytes"
+	"context"
 	"errors"
 	"fmt"
 	"io"
@@ -12,7 +13,7 @@ import (
 	"path"
 	"strings"
 
-	"github.com/ledongthuc/pdf"
+	"github.com/mattermost/pdf"
 
 	"github.com/mattermost/mattermost/server/v8/channels/utils"
 )
@@ -31,7 +32,7 @@ func (pe *pdfExtractor) Match(filename string) bool {
 	return supportedExtensions[extension]
 }
 
-func (pe *pdfExtractor) Extract(filename string, r io.ReadSeeker, maxFileSize int64) (out string, outErr error) {
+func (pe *pdfExtractor) Extract(ctx context.Context, filename string, r io.ReadSeeker, maxFileSize int64) (out string, outErr error) {
 	defer func() {
 		if r := recover(); r != nil {
 			out = ""
@@ -62,7 +63,7 @@ func (pe *pdfExtractor) Extract(filename string, r io.ReadSeeker, maxFileSize in
 	}
 
 	var buf bytes.Buffer
-	b, err := reader.GetPlainText()
+	b, err := reader.GetPlainText(ctx)
 	if err != nil {
 		return "", err
 	}
diff --git a/server/platform/services/docextractor/pdf_test.go b/server/platform/services/docextractor/pdf_test.go
index 5f5ca7e8c73..1b91912087d 100644
--- a/server/platform/services/docextractor/pdf_test.go
+++ b/server/platform/services/docextractor/pdf_test.go
@@ -5,6 +5,7 @@ package docextractor
 
 import (
 	"bytes"
+	"context"
 	"testing"
 
 	"github.com/stretchr/testify/require"
@@ -14,7 +15,7 @@ import (
 
 func TestPdfEmptyFile(t *testing.T) {
 	extractor := pdfExtractor{}
-	_, err := extractor.Extract("test.pdf", bytes.NewReader([]byte{}), 0)
+	_, err := extractor.Extract(context.Background(), "test.pdf", bytes.NewReader([]byte{}), 0)
 	require.Error(t, err)
 }
 
@@ -23,7 +24,7 @@ func TestPdfFile(t *testing.T) {
 	contentText := "\nThis is a simple document that contains some text."
 	content, err := testutils.ReadTestFile("sample-doc.pdf")
 	require.NoError(t, err)
-	extractedText, err := extractor.Extract("sample-doc.pdf", bytes.NewReader(content), 0)
+	extractedText, err := extractor.Extract(context.Background(), "sample-doc.pdf", bytes.NewReader(content), 0)
 	require.NoError(t, err)
 	require.Equal(t, contentText, extractedText)
 }
@@ -38,7 +39,7 @@ func TestPdfDeeplyNestedObjects(t *testing.T) {
 	buf.WriteString("startxref\n0\n%%EOF\n")
 
 	extractor := pdfExtractor{}
-	text, err := extractor.Extract("excessive-nests.pdf", bytes.NewReader(buf.Bytes()), 0)
+	text, err := extractor.Extract(context.Background(), "excessive-nests.pdf", bytes.NewReader(buf.Bytes()), 0)
 	require.Error(t, err)
 	require.Empty(t, text)
 }
@@ -47,10 +48,22 @@ func TestWrongPdfFile(t *testing.T) {
 	extractor := pdfExtractor{}
 	content, err := testutils.ReadTestFile("sample-doc.docx")
 	require.NoError(t, err)
-	_, err = extractor.Extract("sample-doc.pdf", bytes.NewReader(content), 0)
+	_, err = extractor.Extract(context.Background(), "sample-doc.pdf", bytes.NewReader(content), 0)
 	require.Error(t, err)
 }
 
+func TestPdfCancelledContext(t *testing.T) {
+	extractor := pdfExtractor{}
+	content, err := testutils.ReadTestFile("sample-doc.pdf")
+	require.NoError(t, err)
+
+	ctx, cancel := context.WithCancel(context.Background())
+	cancel()
+
+	_, err = extractor.Extract(ctx, "sample-doc.pdf", bytes.NewReader(content), 0)
+	require.ErrorIs(t, err, context.Canceled)
+}
+
 func TestPdfMaxFileSize(t *testing.T) {
 	extractor := pdfExtractor{}
 	content, err := testutils.ReadTestFile("sample-doc.pdf")
@@ -58,13 +71,13 @@ func TestPdfMaxFileSize(t *testing.T) {
 	require.Greater(t, len(content), 16, "fixture must be larger than the tight limit under test")
 
 	t.Run("a zero limit means unlimited and extracts the content", func(t *testing.T) {
-		text, err := extractor.Extract("sample-doc.pdf", bytes.NewReader(content), 0)
+		text, err := extractor.Extract(context.Background(), "sample-doc.pdf", bytes.NewReader(content), 0)
 		require.NoError(t, err)
 		require.Contains(t, text, "simple")
 	})
 
 	t.Run("a generous limit extracts the content", func(t *testing.T) {
-		text, err := extractor.Extract("sample-doc.pdf", bytes.NewReader(content), 10*1024*1024)
+		text, err := extractor.Extract(context.Background(), "sample-doc.pdf", bytes.NewReader(content), 10*1024*1024)
 		require.NoError(t, err)
 		require.Contains(t, text, "simple")
 	})
@@ -72,7 +85,7 @@ func TestPdfMaxFileSize(t *testing.T) {
 	t.Run("a tight limit prevents extraction", func(t *testing.T) {
 		// The reader errors once it reads past the limit, so io.Copy to the
 		// temp file fails and no text is extracted.
-		text, err := extractor.Extract("sample-doc.pdf", bytes.NewReader(content), 16)
+		text, err := extractor.Extract(context.Background(), "sample-doc.pdf", bytes.NewReader(content), 16)
 		require.Error(t, err)
 		require.Empty(t, text)
 	})
diff --git a/server/platform/services/docextractor/plain.go b/server/platform/services/docextractor/plain.go
index b6fff6bd69d..8489ce97d7e 100644
--- a/server/platform/services/docextractor/plain.go
+++ b/server/platform/services/docextractor/plain.go
@@ -4,6 +4,7 @@
 package docextractor
 
 import (
+	"context"
 	"io"
 	"unicode"
 	"unicode/utf8"
@@ -19,7 +20,7 @@ func (pe *plainExtractor) Match(filename string) bool {
 	return true
 }
 
-func (pe *plainExtractor) Extract(filename string, r io.ReadSeeker, _ int64) (string, error) {
+func (pe *plainExtractor) Extract(_ context.Context, filename string, r io.ReadSeeker, _ int64) (string, error) {
 	// This detects any visible character plus any whitespace
 	validRanges := append(unicode.GraphicRanges, unicode.White_Space)
 
diff --git a/server/platform/services/docextractor/plain_test.go b/server/platform/services/docextractor/plain_test.go
index 8e1865e525d..1b3094a6359 100644
--- a/server/platform/services/docextractor/plain_test.go
+++ b/server/platform/services/docextractor/plain_test.go
@@ -5,6 +5,7 @@ package docextractor
 
 import (
 	"bytes"
+	"context"
 	"strings"
 	"testing"
 
@@ -13,7 +14,7 @@ import (
 
 func TestPlainEmptyFile(t *testing.T) {
 	extractor := plainExtractor{}
-	extractedText, err := extractor.Extract("test.txt", bytes.NewReader([]byte{}), 0)
+	extractedText, err := extractor.Extract(context.Background(), "test.txt", bytes.NewReader([]byte{}), 0)
 	require.NoError(t, err)
 	require.Equal(t, "", extractedText)
 }
@@ -21,7 +22,7 @@ func TestPlainEmptyFile(t *testing.T) {
 func TestPlainTextSmallFile(t *testing.T) {
 	extractor := plainExtractor{}
 	content := strings.Repeat("test \n", 5)
-	extractedText, err := extractor.Extract("test.txt", bytes.NewReader([]byte(content)), 0)
+	extractedText, err := extractor.Extract(context.Background(), "test.txt", bytes.NewReader([]byte(content)), 0)
 	require.NoError(t, err)
 	require.Equal(t, content, extractedText)
 }
@@ -29,7 +30,7 @@ func TestPlainTextSmallFile(t *testing.T) {
 func TestPlainBigFile(t *testing.T) {
 	extractor := plainExtractor{}
 	content := strings.Repeat("test \n", 1000)
-	extractedText, err := extractor.Extract("test.txt", bytes.NewReader([]byte(content)), 0)
+	extractedText, err := extractor.Extract(context.Background(), "test.txt", bytes.NewReader([]byte(content)), 0)
 	require.NoError(t, err)
 	require.Equal(t, content, extractedText)
 }
@@ -38,7 +39,7 @@ func TestSmallBinaryFile(t *testing.T) {
 	extractor := plainExtractor{}
 	notUTF8Char := byte(0x7)
 	content := bytes.Repeat([]byte{notUTF8Char}, 1000)
-	extractedText, err := extractor.Extract("test.bin", bytes.NewReader(content), 0)
+	extractedText, err := extractor.Extract(context.Background(), "test.bin", bytes.NewReader(content), 0)
 	require.NoError(t, err)
 	require.Equal(t, "", extractedText)
 }
@@ -47,7 +48,7 @@ func TestBigBinaryFile(t *testing.T) {
 	extractor := plainExtractor{}
 	notUTF8Char := byte(0x7)
 	content := bytes.Repeat([]byte{notUTF8Char}, 10000)
-	extractedText, err := extractor.Extract("test.bin", bytes.NewReader(content), 0)
+	extractedText, err := extractor.Extract(context.Background(), "test.bin", bytes.NewReader(content), 0)
 	require.NoError(t, err)
 	require.Equal(t, "", extractedText)
 }