diff --git a/CHANGELOG_PENDING.md b/CHANGELOG_PENDING.md
index 107daddb70..ac2701c469 100644
--- a/CHANGELOG_PENDING.md
+++ b/CHANGELOG_PENDING.md
@@ -20,6 +20,7 @@
 - \#2103 Suspend sessions that did not pass p-hash verification (@leszko)
 - \#2110 Transparently support HTTP/2 for segment requests while allowing HTTP/1 via GODEBUG runtime flags (@yondonfu)
 - \#2124 Do not retry transcoding if HTTP client closed/canceled the connection (@leszko)
+- \#2122 Add the upload segment timeout to improve failing fast (@leszko)
 
 #### Orchestrator
 
diff --git a/common/util.go b/common/util.go
index c6a432eeb3..b7b43ac500 100644
--- a/common/util.go
+++ b/common/util.go
@@ -29,6 +29,9 @@ import (
 // HTTPTimeout timeout used in HTTP connections between nodes
 var HTTPTimeout = 8 * time.Second
 
+// SegmentUploadTimeout timeout used in HTTP connections for uploading the segment
+var SegmentUploadTimeout = 2 * time.Second
+
 // Max Segment Duration
 var MaxDuration = (5 * time.Minute)
 
diff --git a/server/segment_rpc.go b/server/segment_rpc.go
index d89eee8ec3..c7c0ec4023 100644
--- a/server/segment_rpc.go
+++ b/server/segment_rpc.go
@@ -36,6 +36,9 @@ const segmentHeader = "Livepeer-Segment"
 
 const pixelEstimateMultiplier = 1.02
 
+const segUploadTimeoutMultiplier = 0.5
+const segHttpPushTimeoutMultiplier = 4.0
+
 var errSegEncoding = errors.New("ErrorSegEncoding")
 var errSegSig = errors.New("ErrSegSig")
 var errFormat = errors.New("unrecognized profile output format")
@@ -434,16 +437,24 @@ func SubmitSegment(sess *BroadcastSession, seg *stream.HLSSegment, nonce uint64,
 		return nil, err
 	}
 
+	// timeout for the whole HTTP call: segment upload, transcoding, reading response
+	httpTimeout := common.HTTPTimeout
 	// set a minimum timeout to accommodate transport / processing overhead
-	dur := common.HTTPTimeout
-	paddedDur := 4.0 * seg.Duration // use a multiplier of 4 for now
-	if paddedDur > dur.Seconds() {
-		dur = time.Duration(paddedDur * float64(time.Second))
+	paddedDur := segHttpPushTimeoutMultiplier * seg.Duration
+	if paddedDur > httpTimeout.Seconds() {
+		httpTimeout = time.Duration(paddedDur * float64(time.Second))
+	}
+	// timeout for the segment upload, until HTTP returns OK 200
+	uploadTimeout := time.Duration(segUploadTimeoutMultiplier * seg.Duration * float64(time.Second))
+	if uploadTimeout <= 0 {
+		uploadTimeout = common.SegmentUploadTimeout
 	}
-	ctx, cancel := context.WithTimeout(context.Background(), dur)
+
+	ctx, cancel := context.WithTimeout(context.Background(), httpTimeout)
 	defer cancel()
 
 	ti := sess.OrchestratorInfo
+
 	req, err := http.NewRequestWithContext(ctx, "POST", ti.Transcoder+"/segment", bytes.NewBuffer(data))
 	if err != nil {
 		glog.Errorf("Could not generate transcode request to orch=%s", ti.Transcoder)
@@ -463,9 +474,9 @@ func SubmitSegment(sess *BroadcastSession, seg *stream.HLSSegment, nonce uint64,
 		req.Header.Set("Content-Type", "video/MP2T")
 	}
 
-	glog.Infof("Submitting segment nonce=%d manifestID=%s sessionID=%s seqNo=%d bytes=%v orch=%s timeout=%s", nonce, params.ManifestID, sess.OrchestratorInfo.AuthToken.SessionId, seg.SeqNo, len(data), ti.Transcoder, dur)
+	glog.Infof("Submitting segment nonce=%d manifestID=%s sessionID=%s seqNo=%d bytes=%v orch=%s timeout=%s", nonce, params.ManifestID, sess.OrchestratorInfo.AuthToken.SessionId, seg.SeqNo, len(data), ti.Transcoder, httpTimeout)
 	start := time.Now()
-	resp, err := httpClient.Do(req)
+	resp, err := sendReqWithTimeout(req, uploadTimeout)
 	uploadDur := time.Since(start)
 	if err != nil {
 		glog.Errorf("Unable to submit segment orch=%v nonce=%d manifestID=%s sessionID=%s seqNo=%d orch=%s err=%v", ti.Transcoder, nonce, params.ManifestID, sess.OrchestratorInfo.AuthToken.SessionId, seg.SeqNo, ti.Transcoder, err)
@@ -816,3 +827,20 @@ func validatePrice(sess *BroadcastSession) error {
 	}
 	return nil
 }
+
+func sendReqWithTimeout(req *http.Request, timeout time.Duration) (*http.Response, error) {
+	ctx, cancel := context.WithCancel(req.Context())
+	timeouter := time.AfterFunc(timeout, cancel)
+
+	req = req.WithContext(ctx)
+	resp, err := httpClient.Do(req)
+	if timeouter.Stop() {
+		return resp, err
+	}
+	// timeout has already fired and cancelled the request
+	if err != nil {
+		return nil, err
+	}
+	resp.Body.Close()
+	return nil, context.DeadlineExceeded
+}
diff --git a/server/segment_rpc_test.go b/server/segment_rpc_test.go
index caf879906d..59142bf74f 100644
--- a/server/segment_rpc_test.go
+++ b/server/segment_rpc_test.go
@@ -2,6 +2,7 @@ package server
 
 import (
 	"bytes"
+	"context"
 	"crypto/tls"
 	"encoding/base64"
 	"errors"
@@ -2000,8 +2001,7 @@ func TestSubmitSegment_Timeout(t *testing.T) {
 	headerTimeout = 100 * time.Millisecond
 	lock.Unlock()
 	_, err = SubmitSegment(sess, seg, 0, false, true)
-	assert.Contains(err.Error(), "header timeout")
-	assert.Contains(err.Error(), "context deadline exceeded")
+	assert.Contains(err.Error(), "context canceled")
 
 	// time out body
 	lock.Lock()
@@ -2261,6 +2261,30 @@ func TestSubmitSegment_Success(t *testing.T) {
 	balance.AssertCalled(t, "Credit", ratMatcher(change))
 }
 
+func TestSendReqWithTimeout(t *testing.T) {
+	assert := assert.New(t)
+
+	var wg sync.WaitGroup
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		wg.Wait()
+		w.WriteHeader(http.StatusOK)
+	}))
+	defer server.Close()
+	req, _ := http.NewRequestWithContext(context.Background(), "POST", server.URL, nil)
+
+	// no timeout
+	resp, err := sendReqWithTimeout(req, 5*time.Second)
+	assert.NoError(err)
+	assert.Equal(200, resp.StatusCode)
+
+	// timeout
+	wg.Add(1)
+	resp, err = sendReqWithTimeout(req, time.Millisecond)
+	wg.Done()
+	assert.Nil(resp)
+	assert.ErrorIs(err, context.Canceled)
+}
+
 func stubTLSServer() (*httptest.Server, *http.ServeMux) {
 	mux := http.NewServeMux()