diff --git a/.vscode/launch.json b/.vscode/launch.json
index 55f314e399e2c..2c7030df187ba 100644
--- a/.vscode/launch.json
+++ b/.vscode/launch.json
@@ -5,7 +5,7 @@
   "version": "0.2.0",
   "configurations": [
     {
-      "name": "Basic Turbo Build",
+      "name": "Build Basic",
       "type": "go",
       "request": "launch",
       "mode": "debug",
@@ -21,6 +21,15 @@
       "program": "${workspaceRoot}/cli/cmd/turbo",
       "cwd": "${workspaceRoot}/examples/basic",
       "args": ["--version"]
+    },
+    {
+      "name": "Build All (Force)",
+      "type": "go",
+      "request": "launch",
+      "mode": "debug",
+      "program": "${workspaceRoot}/cli/cmd/turbo",
+      "cwd": "${workspaceRoot}",
+      "args": ["run", "build", "--force"]
     }
   ]
 }
diff --git a/cli/internal/client/client.go b/cli/internal/client/client.go
index e7f4aca6710c9..30e5b0cd6f884 100644
--- a/cli/internal/client/client.go
+++ b/cli/internal/client/client.go
@@ -2,7 +2,9 @@ package client
 
 import (
 	"context"
+	"crypto/md5"
 	"crypto/x509"
+	"encoding/base64"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -132,7 +134,7 @@ func (c *ApiClient) UserAgent() string {
 	return fmt.Sprintf("turbo %v %v %v (%v)", c.turboVersion, runtime.Version(), runtime.GOOS, runtime.GOARCH)
 }
 
-func (c *ApiClient) PutArtifact(hash string, duration int, rawBody interface{}) error {
+func (c *ApiClient) PutArtifact(hash string, duration int, artifactReader io.Reader) error {
 	if err := c.okToRequest(); err != nil {
 		return err
 	}
@@ -143,11 +145,28 @@ func (c *ApiClient) PutArtifact(hash string, duration int, rawBody interface{})
 	if encoded != "" {
 		encoded = "?" + encoded
 	}
-	req, err := retryablehttp.NewRequest(http.MethodPut, c.makeUrl("/v8/artifacts/"+hash+encoded), rawBody)
+	// Read the entire artifactReader into memory so we can easily compute the Content-MD5.
+	// Note: retryablehttp.NewRequest reads the artifactReader into memory so there's no
+	// additional overhead by doing the ioutil.ReadAll here instead.
+	artifactBody, err := ioutil.ReadAll(artifactReader)
+	if err != nil {
+		return fmt.Errorf("failed to store files in HTTP cache: %w", err)
+	}
+	md5Sum := md5.Sum(artifactBody)
+	contentMd5 := base64.StdEncoding.EncodeToString(md5Sum[:])
+
+	req, err := retryablehttp.NewRequest(http.MethodPut, c.makeUrl("/v8/artifacts/"+hash+encoded), artifactBody)
+	// We need to initialize the trailer since it's not auto-initialized by the http module
+	req.Trailer = make(http.Header)
+	req.Trailer.Add("Content-MD5", contentMd5)
+	// ContentLenth -1 is required to set trailers on the http request.
+	req.ContentLength = -1
 	req.Header.Set("Content-Type", "application/octet-stream")
 	req.Header.Set("x-artifact-duration", fmt.Sprintf("%v", duration))
 	req.Header.Set("Authorization", "Bearer "+c.Token)
 	req.Header.Set("User-Agent", c.UserAgent())
+	req.Header.Set("Trailer", "Content-MD5")
+
 	if err != nil {
 		return fmt.Errorf("[WARNING] Invalid cache URL: %w", err)
 	}
diff --git a/cli/internal/client/client_test.go b/cli/internal/client/client_test.go
index e534f43f436f0..3f9b61d2067c7 100644
--- a/cli/internal/client/client_test.go
+++ b/cli/internal/client/client_test.go
@@ -1,10 +1,14 @@
 package client
 
 import (
+	"crypto/md5"
+	"encoding/base64"
 	"encoding/json"
 	"io/ioutil"
 	"net/http"
+	"net/http/httptest"
 	"reflect"
+	"strings"
 	"testing"
 
 	"github.com/google/uuid"
@@ -12,22 +16,21 @@ import (
 )
 
 func Test_sendToServer(t *testing.T) {
-	handler := http.NewServeMux()
 	ch := make(chan []byte, 1)
-	handler.HandleFunc("/v8/artifacts/events", func(w http.ResponseWriter, req *http.Request) {
-		defer req.Body.Close()
-		b, err := ioutil.ReadAll(req.Body)
-		if err != nil {
-			t.Errorf("failed to read request %v", err)
-		}
-		ch <- b
-		w.WriteHeader(200)
-		w.Write([]byte{})
-	})
-	server := &http.Server{Addr: "localhost:8888", Handler: handler}
-	go server.ListenAndServe()
+	ts := httptest.NewServer(
+		http.HandlerFunc(func(w http.ResponseWriter, req *http.Request) {
+			defer req.Body.Close()
+			b, err := ioutil.ReadAll(req.Body)
+			if err != nil {
+				t.Errorf("failed to read request %v", err)
+			}
+			ch <- b
+			w.WriteHeader(200)
+			w.Write([]byte{})
+		}))
+	defer ts.Close()
 
-	apiClient := NewClient("http://localhost:8888", hclog.Default(), "v1", "", "my-team-slug", 1)
+	apiClient := NewClient(ts.URL, hclog.Default(), "v1", "", "my-team-slug", 1)
 	apiClient.SetToken("my-token")
 
 	myUUID, err := uuid.NewUUID()
@@ -61,6 +64,42 @@ func Test_sendToServer(t *testing.T) {
 	if !reflect.DeepEqual(events, result) {
 		t.Errorf("roundtrip got %v, want %v", result, events)
 	}
+}
+
+func Test_PutArtifact(t *testing.T) {
+	ch := make(chan string, 2)
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, req *http.Request) {
+		defer req.Body.Close()
+		b, err := ioutil.ReadAll(req.Body)
+		if err != nil {
+			t.Errorf("failed to read request %v", err)
+		}
+		ch <- string(b)
+		trailerMd5 := req.Trailer.Get("Content-MD5")
+		ch <- trailerMd5
+		w.WriteHeader(200)
+		w.Write([]byte{})
+	}))
+	defer ts.Close()
+
+	// Set up test expected values
+	apiClient := NewClient(ts.URL+"/hash", hclog.Default(), "v1", "", "my-team-slug", 1)
+	apiClient.SetToken("my-token")
+	expectedArtifactBody := "My string artifact"
+	artifactReader := strings.NewReader(expectedArtifactBody)
+	md5Sum := md5.Sum([]byte(expectedArtifactBody))
+	expectedMd5 := base64.StdEncoding.EncodeToString(md5Sum[:])
+
+	// Test Put Artifact
+	apiClient.PutArtifact("hash", 500, artifactReader)
+	testBody := <-ch
+	if expectedArtifactBody != testBody {
+		t.Errorf("Handler read '%v', wants '%v'", testBody, expectedArtifactBody)
+	}
+
+	testMd5 := <-ch
+	if expectedMd5 != testMd5 {
+		t.Errorf("Handler read trailer '%v', wants '%v'", testMd5, expectedMd5)
+	}
 
-	server.Close()
 }