diff --git a/cli/internal/cache/cache.go b/cli/internal/cache/cache.go
index e38ee2952f41a..a850df075b0f6 100644
--- a/cli/internal/cache/cache.go
+++ b/cli/internal/cache/cache.go
@@ -3,9 +3,10 @@ package cache
 
 import (
 	"fmt"
-	"sync"
+
 	"github.com/vercel/turborepo/cli/internal/config"
 	"github.com/vercel/turborepo/cli/internal/ui"
+	"golang.org/x/sync/errgroup"
 )
 
 // Cache is abstracted way to cache/fetch previously run tasks
@@ -53,8 +54,7 @@ type cacheMultiplexer struct {
 }
 
 func (mplex cacheMultiplexer) Put(target string, key string, duration int, files []string) error {
-	mplex.storeUntil(target, key, duration, files, len(mplex.caches))
-	return nil
+	return mplex.storeUntil(target, key, duration, files, len(mplex.caches))
 }
 
 // storeUntil stores artifacts into higher priority caches than the given one.
@@ -62,30 +62,36 @@ func (mplex cacheMultiplexer) Put(target string, key string, duration int, files
 // downloading from the RPC cache.
 // This is a little inefficient since we could write the file to plz-out then copy it to the dir cache,
 // but it's hard to fix that without breaking the cache abstraction.
-func (mplex cacheMultiplexer) storeUntil(target string, key string, duration int, outputGlobs []string, stopAt int) {
+func (mplex cacheMultiplexer) storeUntil(target string, key string, duration int, outputGlobs []string, stopAt int) error {
 	// Attempt to store on all caches simultaneously.
-	var wg sync.WaitGroup
+	g := &errgroup.Group{}
 	for i, cache := range mplex.caches {
 		if i == stopAt {
 			break
 		}
-		wg.Add(1)
-		go func(cache Cache) {
-			cache.Put(target, key, duration, outputGlobs)
-			wg.Done()
-		}(cache)
+		c := cache
+		g.Go(func() error {
+			return c.Put(target, key, duration, outputGlobs)
+		})
+	}
+
+	if err := g.Wait(); err != nil {
+		return err
 	}
-	wg.Wait()
+
+	return nil
 }
 
 func (mplex cacheMultiplexer) Fetch(target string, key string, files []string) (bool, []string, error) {
 	// Retrieve from caches sequentially; if we did them simultaneously we could
 	// easily write the same file from two goroutines at once.
 	for i, cache := range mplex.caches {
-		if ok, actualFiles, _ := cache.Fetch(target, key, files); ok {
-			// Store this into other caches
+		if ok, actualFiles, err := cache.Fetch(target, key, files); ok {
+			// Store this into other caches. We can ignore errors here because we know
+			// we have previously successfully stored in a higher-priority cache, and so the overall
+			// result is a success at fetching. Storing in lower-priority caches is an optimization.
 			mplex.storeUntil(target, key, 0, actualFiles, i)
-			return ok, actualFiles, nil
+			return ok, actualFiles, err
 		}
 	}
 	return false, files, nil
diff --git a/cli/internal/cache/cache_http.go b/cli/internal/cache/cache_http.go
index 2ec1535672391..9fd835e987298 100644
--- a/cli/internal/cache/cache_http.go
+++ b/cli/internal/cache/cache_http.go
@@ -41,6 +41,7 @@ func (cache *httpCache) Put(target, hash string, duration int, files []string) e
 	// if cache.writable {
 	cache.requestLimiter.acquire()
 	defer cache.requestLimiter.release()
+
 	r, w := io.Pipe()
 	go cache.write(w, hash, files)
 	return cache.config.ApiClient.PutArtifact(hash, cache.config.TeamId, cache.config.TeamSlug, duration, r)
diff --git a/cli/internal/client/client.go b/cli/internal/client/client.go
index a5097d9a501b5..704d98b90fd05 100644
--- a/cli/internal/client/client.go
+++ b/cli/internal/client/client.go
@@ -1,7 +1,10 @@
 package client
 
 import (
+	"context"
+	"crypto/x509"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"io"
 	"io/ioutil"
@@ -9,6 +12,7 @@ import (
 	"net/url"
 	"runtime"
 	"strings"
+	"sync/atomic"
 	"time"
 
 	"github.com/hashicorp/go-hclog"
@@ -20,31 +24,99 @@ type ApiClient struct {
 	baseUrl      string
 	Token        string
 	turboVersion string
+	// Number of failed requests before we stop trying to upload/download artifacts to the remote cache
+	maxRemoteFailCount uint64
+	// Must be used via atomic package
+	currentFailCount uint64
 	// An http client
 	HttpClient *retryablehttp.Client
 }
 
+// ErrTooManyFailures is returned from remote cache API methods after `maxRemoteFailCount` errors have occurred
+var ErrTooManyFailures = errors.New("skipping HTTP Request, too many failures have occurred")
+
 func (api *ApiClient) SetToken(token string) {
 	api.Token = token
 }
 
 // New creates a new ApiClient
-func NewClient(baseUrl string, logger hclog.Logger, turboVersion string) *ApiClient {
-	return &ApiClient{
-		baseUrl:      baseUrl,
-		turboVersion: turboVersion,
+func NewClient(baseUrl string, logger hclog.Logger, turboVersion string, maxRemoteFailCount uint64) *ApiClient {
+	client := &ApiClient{
+		baseUrl:            baseUrl,
+		turboVersion:       turboVersion,
+		maxRemoteFailCount: maxRemoteFailCount,
 		HttpClient: &retryablehttp.Client{
 			HTTPClient: &http.Client{
-				Timeout: time.Duration(60 * time.Second),
+				Timeout: time.Duration(20 * time.Second),
 			},
-			RetryWaitMin: 10 * time.Second,
-			RetryWaitMax: 20 * time.Second,
-			RetryMax:     5,
-			CheckRetry:   retryablehttp.DefaultRetryPolicy,
+			RetryWaitMin: 2 * time.Second,
+			RetryWaitMax: 10 * time.Second,
+			RetryMax:     2,
 			Backoff:      retryablehttp.DefaultBackoff,
 			Logger:       logger,
 		},
 	}
+	client.HttpClient.CheckRetry = client.checkRetry
+	return client
+}
+
+func (c *ApiClient) retryCachePolicy(resp *http.Response, err error) (bool, error) {
+	if err != nil {
+		if errors.As(err, &x509.UnknownAuthorityError{}) {
+			// Don't retry if the error was due to TLS cert verification failure.
+			atomic.AddUint64(&c.currentFailCount, 1)
+			return false, err
+		}
+		atomic.AddUint64(&c.currentFailCount, 1)
+		return true, nil
+	}
+
+	// 429 Too Many Requests is recoverable. Sometimes the server puts
+	// a Retry-After response header to indicate when the server is
+	// available to start processing request from client.
+	if resp.StatusCode == http.StatusTooManyRequests {
+		atomic.AddUint64(&c.currentFailCount, 1)
+		return true, nil
+	}
+
+	// Check the response code. We retry on 500-range responses to allow
+	// the server time to recover, as 500's are typically not permanent
+	// errors and may relate to outages on the server side. This will catch
+	// invalid response codes as well, like 0 and 999.
+	if resp.StatusCode == 0 || (resp.StatusCode >= 500 && resp.StatusCode != 501) {
+		atomic.AddUint64(&c.currentFailCount, 1)
+		return true, fmt.Errorf("unexpected HTTP status %s", resp.Status)
+	}
+
+	return false, fmt.Errorf("unexpected HTTP status %s", resp.Status)
+}
+
+func (c *ApiClient) checkRetry(ctx context.Context, resp *http.Response, err error) (bool, error) {
+	// do not retry on context.Canceled or context.DeadlineExceeded
+	if ctx.Err() != nil {
+		atomic.AddUint64(&c.currentFailCount, 1)
+		return false, ctx.Err()
+	}
+
+	// we're squashing the error from the request and substituting any error that might come
+	// from our retry policy.
+	shouldRetry, err := c.retryCachePolicy(resp, err)
+	if shouldRetry {
+		// Our policy says it's ok to retry, but we need to check the failure count
+		if retryErr := c.okToRequest(); retryErr != nil {
+			return false, retryErr
+		}
+	}
+	return shouldRetry, err
+}
+
+// okToRequest returns nil if it's ok to make a request, and returns the error to
+// return to the caller if a request is not allowed
+func (c *ApiClient) okToRequest() error {
+	if atomic.LoadUint64(&c.currentFailCount) < c.maxRemoteFailCount {
+		return nil
+	}
+	return ErrTooManyFailures
 }
 
 func (c *ApiClient) makeUrl(endpoint string) string {
@@ -56,6 +128,9 @@ func (c *ApiClient) UserAgent() string {
 }
 
 func (c *ApiClient) PutArtifact(hash string, teamId string, slug string, duration int, rawBody interface{}) error {
+	if err := c.okToRequest(); err != nil {
+		return err
+	}
 	params := url.Values{}
 	if teamId != "" && strings.HasPrefix(teamId, "team_") {
 		params.Add("teamId", teamId)
@@ -63,7 +138,12 @@ func (c *ApiClient) PutArtifact(hash string, teamId string, slug string, duratio
 	if slug != "" {
 		params.Add("slug", slug)
 	}
-	req, err := retryablehttp.NewRequest(http.MethodPut, c.makeUrl("/v8/artifacts/"+hash+"?"+params.Encode()), rawBody)
+	// only add a ? if it's actually needed (makes logging cleaner)
+	encoded := params.Encode()
+	if encoded != "" {
+		encoded = "?" + encoded
+	}
+	req, err := retryablehttp.NewRequest(http.MethodPut, c.makeUrl("/v8/artifacts/"+hash+encoded), rawBody)
 	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)
@@ -71,6 +151,7 @@ func (c *ApiClient) PutArtifact(hash string, teamId string, slug string, duratio
 	if err != nil {
 		return fmt.Errorf("[WARNING] Invalid cache URL: %w", err)
 	}
+
 	if resp, err := c.HttpClient.Do(req); err != nil {
 		return fmt.Errorf("failed to store files in HTTP cache: %w", err)
 	} else {
@@ -80,6 +161,9 @@ func (c *ApiClient) PutArtifact(hash string, teamId string, slug string, duratio
 }
 
 func (c *ApiClient) FetchArtifact(hash string, teamId string, slug string, rawBody interface{}) (*http.Response, error) {
+	if err := c.okToRequest(); err != nil {
+		return nil, err
+	}
 	params := url.Values{}
 	if teamId != "" && strings.HasPrefix(teamId, "team_") {
 		params.Add("teamId", teamId)
@@ -87,12 +171,18 @@ func (c *ApiClient) FetchArtifact(hash string, teamId string, slug string, rawBo
 	if slug != "" {
 		params.Add("slug", slug)
 	}
-	req, err := retryablehttp.NewRequest(http.MethodGet, c.makeUrl("/v8/artifacts/"+hash+"?"+params.Encode()), nil)
+	// only add a ? if it's actually needed (makes logging cleaner)
+	encoded := params.Encode()
+	if encoded != "" {
+		encoded = "?" + encoded
+	}
+	req, err := retryablehttp.NewRequest(http.MethodGet, c.makeUrl("/v8/artifacts/"+hash+encoded), nil)
 	req.Header.Set("Authorization", "Bearer "+c.Token)
 	req.Header.Set("User-Agent", c.UserAgent())
 	if err != nil {
-		return nil, fmt.Errorf("[WARNING] Invalid cache URL: %w", err)
+		return nil, fmt.Errorf("invalid cache URL: %w", err)
 	}
+
 	return c.HttpClient.Do(req)
 }
 
diff --git a/cli/internal/config/config.go b/cli/internal/config/config.go
index 74768dca95d9c..5241a2cee09b6 100644
--- a/cli/internal/config/config.go
+++ b/cli/internal/config/config.go
@@ -9,6 +9,7 @@ import (
 	"path/filepath"
 	"runtime"
 	"strings"
+
 	"github.com/vercel/turborepo/cli/internal/client"
 
 	hclog "github.com/hashicorp/go-hclog"
@@ -53,8 +54,6 @@ type CacheConfig struct {
 	Workers int
 	// Cache directory
 	Dir string
-	// HTTP URI of the cache
-	Url string
 }
 
 // ParseAndValidate parses the cmd line flags / env vars, and verifies that all required
@@ -162,7 +161,8 @@ func ParseAndValidate(args []string, ui cli.Ui, turboVersion string) (c *Config,
 		Output: output,
 	})
 
-	apiClient := client.NewClient(partialConfig.ApiUrl, logger, turboVersion)
+	maxRemoteFailCount := 3
+	apiClient := client.NewClient(partialConfig.ApiUrl, logger, turboVersion, uint64(maxRemoteFailCount))
 
 	c = &Config{
 		Logger:       logger,