diff --git a/CHANGELOG.md b/CHANGELOG.md
index 83e0219bad..8955ce687e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -13,6 +13,8 @@ All notable changes to `src-cli` are documented in this file.
 
 ### Added
 
+- Add verbosity flag to `lsif upload` action. Supply `-trace=1`, `-trace=2`, or `-trace=3` to the action to specify verbosity.
+
 ### Changed
 
 ### Fixed
diff --git a/cmd/src/lsif_upload.go b/cmd/src/lsif_upload.go
index 7f3d785d64..e653321af3 100644
--- a/cmd/src/lsif_upload.go
+++ b/cmd/src/lsif_upload.go
@@ -4,14 +4,15 @@ import (
 	"encoding/json"
 	"flag"
 	"fmt"
+	"net/http"
 	"net/url"
 	"os"
+	"sort"
 	"strings"
 	"sync"
 	"time"
 
 	"github.com/efritz/pentimento"
-	"github.com/mattn/go-isatty"
 	"github.com/pkg/browser"
 	"github.com/pkg/errors"
 	"github.com/sourcegraph/codeintelutils"
@@ -52,6 +53,8 @@ Examples:
 		maxPayloadSizeMb     *int
 		ignoreUploadFailures *bool
 		uploadRoute          *string
+		rawVerbosity         *int
+		verbosity            lsifUploadVerbosity
 	}
 
 	flagSet := flag.NewFlagSet("upload", flag.ExitOnError)
@@ -67,6 +70,7 @@ Examples:
 	flags.maxPayloadSizeMb = flagSet.Int("max-payload-size", 100, `The maximum upload size (in megabytes). Indexes exceeding this limit will be uploaded over multiple HTTP requests.`)
 	flags.ignoreUploadFailures = flagSet.Bool("ignore-upload-failure", false, `Exit with status code zero on upload failure.`)
 	flags.uploadRoute = flagSet.String("upload-route", "/.api/lsif/upload", "The path of the upload route.")
+	flags.rawVerbosity = flagSet.Int("trace", 0, "-trace=0 shows no logs; -trace=1 shows requests and response metadata; -trace=2 shows headers, -trace=3 shows response body")
 
 	parseAndValidateFlags := func(args []string) error {
 		flagSet.Parse(args)
@@ -146,6 +150,12 @@ Examples:
 			return errors.New("max-payload-size must be positive")
 		}
 
+		// Don't need to check upper bounds as we only compare verbosity ranges
+		// It's fine if someone supplies -trace=42, but it will just behave the
+		// same as if they supplied the highest verbosity level we define
+		// internally.
+		flags.verbosity = lsifUploadVerbosity(*flags.rawVerbosity)
+
 		if !*flags.json {
 			fmt.Println(argsString)
 		}
@@ -173,6 +183,7 @@ Examples:
 			MaxRetries:           10,
 			RetryInterval:        time.Millisecond * 250,
 			UploadProgressEvents: make(chan codeintelutils.UploadProgressEvent),
+			Logger:               &lsifUploadRequestLogger{verbosity: flags.verbosity},
 		}
 
 		var wg sync.WaitGroup
@@ -181,7 +192,7 @@ Examples:
 		go func() {
 			defer wg.Done()
 
-			if *flags.json || *flags.noProgress {
+			if *flags.json || *flags.noProgress || flags.verbosity > 0 {
 				return
 			}
 
@@ -202,19 +213,19 @@ Examples:
 		wg.Wait()                        // Wait for progress bar goroutine to clear screen
 		if err != nil {
 			if err == codeintelutils.ErrUnauthorized {
-				if *flags.gitHubToken == "" {
-					return fmt.Errorf("you must provide -github-token=TOKEN, where TOKEN is a GitHub personal access token with 'repo' or 'public_repo' scope")
+				err = errorWithHint{
+					err: err, hint: strings.Join([]string{
+						"You may need to specify or update your GitHub access token to use this endpoint.",
+						"See https://docs.sourcegraph.com/cli/references/lsif/upload.",
+					}, "\n"),
 				}
 
-				if isatty.IsTerminal(os.Stdout.Fd()) {
-					fmt.Println("You may need to specify or update your GitHub access token to use this endpoint.")
-					fmt.Println("See https://github.com/sourcegraph/src-cli#authentication.")
-				}
 			}
 
 			if *flags.ignoreUploadFailures {
-				fmt.Printf("error: %s\n", err)
-				return nil
+				// Report but don't return
+				fmt.Println(err.Error())
+				err = nil
 			}
 
 			return err
@@ -312,3 +323,76 @@ func digits(n int) int {
 	}
 	return 1
 }
+
+type errorWithHint struct {
+	err  error
+	hint string
+}
+
+func (e errorWithHint) Error() string {
+	return fmt.Sprintf("error: %s\n\n%s\n", e.err, e.hint)
+}
+
+type lsifUploadVerbosity int
+
+const (
+	lsifUploadVerbosityNone                  lsifUploadVerbosity = iota // -trace=0 (default)
+	lsifUploadVerbosityTrace                                            // -trace=1
+	lsifUploadVerbosityTraceShowHeaders                                 // -trace=2
+	lsifUploadVerbosityTraceShowResponseBody                            // -trace=3
+)
+
+type lsifUploadRequestLogger struct {
+	verbosity lsifUploadVerbosity
+}
+
+func (l *lsifUploadRequestLogger) LogRequest(req *http.Request) {
+	if l.verbosity == lsifUploadVerbosityNone {
+		return
+	}
+
+	if l.verbosity >= lsifUploadVerbosityTrace {
+		fmt.Printf("> %s %s\n", req.Method, req.URL)
+	}
+
+	if l.verbosity >= lsifUploadVerbosityTraceShowHeaders {
+		fmt.Printf("> Request Headers:\n")
+		for _, k := range sortHeaders(req.Header) {
+			fmt.Printf(">     %s: %s\n", k, req.Header[k])
+		}
+	}
+
+	fmt.Printf("\n")
+}
+
+func (l *lsifUploadRequestLogger) LogResponse(req *http.Request, resp *http.Response, body []byte, elapsed time.Duration) {
+	if l.verbosity == lsifUploadVerbosityNone {
+		return
+	}
+
+	if l.verbosity >= lsifUploadVerbosityTrace {
+		fmt.Printf("< %s %s %s in %s\n", req.Method, req.URL, resp.Status, elapsed)
+	}
+
+	if l.verbosity >= lsifUploadVerbosityTraceShowHeaders {
+		fmt.Printf("< Response Headers:\n")
+		for _, k := range sortHeaders(resp.Header) {
+			fmt.Printf("<     %s: %s\n", k, resp.Header[k])
+		}
+	}
+
+	if l.verbosity >= lsifUploadVerbosityTraceShowResponseBody {
+		fmt.Printf("< Response Body: %s\n", body)
+	}
+
+	fmt.Printf("\n")
+}
+
+func sortHeaders(header http.Header) []string {
+	var keys []string
+	for k := range header {
+		keys = append(keys, k)
+	}
+	sort.Strings(keys)
+	return keys
+}
diff --git a/go.mod b/go.mod
index ebe9209de1..e12b4fb797 100644
--- a/go.mod
+++ b/go.mod
@@ -21,7 +21,7 @@ require (
 	github.com/pkg/browser v0.0.0-20180916011732-0a3d74bf9ce4
 	github.com/pkg/errors v0.9.1
 	github.com/sourcegraph/campaignutils v0.0.0-20201124055807-2f9cfa9317e2
-	github.com/sourcegraph/codeintelutils v0.0.0-20201118031531-b82ba3167b30
+	github.com/sourcegraph/codeintelutils v0.0.0-20210113171425-9ec641b48a8e
 	github.com/sourcegraph/go-diff v0.6.1
 	github.com/sourcegraph/jsonx v0.0.0-20200629203448-1a936bd500cf
 	github.com/ssor/bom v0.0.0-20170718123548-6386211fdfcf // indirect
diff --git a/go.sum b/go.sum
index d569c1db34..bcbbeb1b3a 100644
--- a/go.sum
+++ b/go.sum
@@ -52,8 +52,8 @@ github.com/shurcooL/go v0.0.0-20180423040247-9e1955d9fb6e/go.mod h1:TDJrrUr11Vxr
 github.com/shurcooL/go-goon v0.0.0-20170922171312-37c2f522c041/go.mod h1:N5mDOmsrJOB+vfqUK+7DmDyjhSLIIBnXo9lvZJj3MWQ=
 github.com/sourcegraph/campaignutils v0.0.0-20201124055807-2f9cfa9317e2 h1:MJu/6WzWdPegzYnZLb04IS0u4VyUpPIAHQyWT5i2vR8=
 github.com/sourcegraph/campaignutils v0.0.0-20201124055807-2f9cfa9317e2/go.mod h1:xm6i78Mk2t4DBLQDqEFc/3x6IPf7yYZCgbNaTQGhJHA=
-github.com/sourcegraph/codeintelutils v0.0.0-20201118031531-b82ba3167b30 h1:HrRrPyskdkHc6MqQS3ehH+DSraFnOhtvBWQ6AzEJC1o=
-github.com/sourcegraph/codeintelutils v0.0.0-20201118031531-b82ba3167b30/go.mod h1:HplI8gRslTrTUUsSYwu28hSOderix7m5dHNca7xBzeo=
+github.com/sourcegraph/codeintelutils v0.0.0-20210113171425-9ec641b48a8e h1:PdNc6fH0HHQ5xbnCwPkHuFdVCofQilFm9gG40fEQKms=
+github.com/sourcegraph/codeintelutils v0.0.0-20210113171425-9ec641b48a8e/go.mod h1:HplI8gRslTrTUUsSYwu28hSOderix7m5dHNca7xBzeo=
 github.com/sourcegraph/go-diff v0.6.1 h1:hmA1LzxW0n1c3Q4YbrFgg4P99GSnebYa3x8gr0HZqLQ=
 github.com/sourcegraph/go-diff v0.6.1/go.mod h1:iBszgVvyxdc8SFZ7gm69go2KDdt3ag071iBaWPF6cjs=
 github.com/sourcegraph/jsonx v0.0.0-20200629203448-1a936bd500cf h1:oAdWFqhStsWiiMP/vkkHiMXqFXzl1XfUNOdxKJbd6bI=