diff --git a/coderd/database/dump.sql b/coderd/database/dump.sql
index 7bea770248310..859cdd4b9ce6c 100644
--- a/coderd/database/dump.sql
+++ b/coderd/database/dump.sql
@@ -942,13 +942,16 @@ CREATE TABLE external_auth_links (
     oauth_expiry timestamp with time zone NOT NULL,
     oauth_access_token_key_id text,
     oauth_refresh_token_key_id text,
-    oauth_extra jsonb
+    oauth_extra jsonb,
+    oauth_refresh_failure_reason text DEFAULT ''::text NOT NULL
 );
 
 COMMENT ON COLUMN external_auth_links.oauth_access_token_key_id IS 'The ID of the key used to encrypt the OAuth access token. If this is NULL, the access token is not encrypted';
 
 COMMENT ON COLUMN external_auth_links.oauth_refresh_token_key_id IS 'The ID of the key used to encrypt the OAuth refresh token. If this is NULL, the refresh token is not encrypted';
 
+COMMENT ON COLUMN external_auth_links.oauth_refresh_failure_reason IS 'This error means the refresh token is invalid. Cached so we can avoid calling the external provider again for the same error.';
+
 CREATE TABLE files (
     hash character varying(64) NOT NULL,
     created_at timestamp with time zone NOT NULL,
diff --git a/coderd/database/migrations/000358_failed_ext_auth_error.down.sql b/coderd/database/migrations/000358_failed_ext_auth_error.down.sql
new file mode 100644
index 0000000000000..72cad82d36a1e
--- /dev/null
+++ b/coderd/database/migrations/000358_failed_ext_auth_error.down.sql
@@ -0,0 +1,3 @@
+ALTER TABLE external_auth_links
+	DROP COLUMN oauth_refresh_failure_reason
+;
diff --git a/coderd/database/migrations/000358_failed_ext_auth_error.up.sql b/coderd/database/migrations/000358_failed_ext_auth_error.up.sql
new file mode 100644
index 0000000000000..f2030ecbeeca2
--- /dev/null
+++ b/coderd/database/migrations/000358_failed_ext_auth_error.up.sql
@@ -0,0 +1,7 @@
+ALTER TABLE external_auth_links
+	ADD COLUMN oauth_refresh_failure_reason TEXT NOT NULL DEFAULT ''
+;
+
+COMMENT ON COLUMN external_auth_links.oauth_refresh_failure_reason IS
+	'This error means the refresh token is invalid. Cached so we can avoid calling the external provider again for the same error.'
+;
diff --git a/coderd/database/models.go b/coderd/database/models.go
index 75d2b941dab3c..057d7956e5bbd 100644
--- a/coderd/database/models.go
+++ b/coderd/database/models.go
@@ -3065,6 +3065,8 @@ type ExternalAuthLink struct {
 	// The ID of the key used to encrypt the OAuth refresh token. If this is NULL, the refresh token is not encrypted
 	OAuthRefreshTokenKeyID sql.NullString        `db:"oauth_refresh_token_key_id" json:"oauth_refresh_token_key_id"`
 	OAuthExtra             pqtype.NullRawMessage `db:"oauth_extra" json:"oauth_extra"`
+	// This error means the refresh token is invalid. Cached so we can avoid calling the external provider again for the same error.
+	OauthRefreshFailureReason string `db:"oauth_refresh_failure_reason" json:"oauth_refresh_failure_reason"`
 }
 
 type File struct {
diff --git a/coderd/database/queries.sql.go b/coderd/database/queries.sql.go
index 58874cb7ed8c8..22aec98794fb3 100644
--- a/coderd/database/queries.sql.go
+++ b/coderd/database/queries.sql.go
@@ -1711,7 +1711,7 @@ func (q *sqlQuerier) DeleteExternalAuthLink(ctx context.Context, arg DeleteExter
 }
 
 const getExternalAuthLink = `-- name: GetExternalAuthLink :one
-SELECT provider_id, user_id, created_at, updated_at, oauth_access_token, oauth_refresh_token, oauth_expiry, oauth_access_token_key_id, oauth_refresh_token_key_id, oauth_extra FROM external_auth_links WHERE provider_id = $1 AND user_id = $2
+SELECT provider_id, user_id, created_at, updated_at, oauth_access_token, oauth_refresh_token, oauth_expiry, oauth_access_token_key_id, oauth_refresh_token_key_id, oauth_extra, oauth_refresh_failure_reason FROM external_auth_links WHERE provider_id = $1 AND user_id = $2
 `
 
 type GetExternalAuthLinkParams struct {
@@ -1733,12 +1733,13 @@ func (q *sqlQuerier) GetExternalAuthLink(ctx context.Context, arg GetExternalAut
 		&i.OAuthAccessTokenKeyID,
 		&i.OAuthRefreshTokenKeyID,
 		&i.OAuthExtra,
+		&i.OauthRefreshFailureReason,
 	)
 	return i, err
 }
 
 const getExternalAuthLinksByUserID = `-- name: GetExternalAuthLinksByUserID :many
-SELECT provider_id, user_id, created_at, updated_at, oauth_access_token, oauth_refresh_token, oauth_expiry, oauth_access_token_key_id, oauth_refresh_token_key_id, oauth_extra FROM external_auth_links WHERE user_id = $1
+SELECT provider_id, user_id, created_at, updated_at, oauth_access_token, oauth_refresh_token, oauth_expiry, oauth_access_token_key_id, oauth_refresh_token_key_id, oauth_extra, oauth_refresh_failure_reason FROM external_auth_links WHERE user_id = $1
 `
 
 func (q *sqlQuerier) GetExternalAuthLinksByUserID(ctx context.Context, userID uuid.UUID) ([]ExternalAuthLink, error) {
@@ -1761,6 +1762,7 @@ func (q *sqlQuerier) GetExternalAuthLinksByUserID(ctx context.Context, userID uu
 			&i.OAuthAccessTokenKeyID,
 			&i.OAuthRefreshTokenKeyID,
 			&i.OAuthExtra,
+			&i.OauthRefreshFailureReason,
 		); err != nil {
 			return nil, err
 		}
@@ -1798,7 +1800,7 @@ INSERT INTO external_auth_links (
     $8,
     $9,
 	$10
-) RETURNING provider_id, user_id, created_at, updated_at, oauth_access_token, oauth_refresh_token, oauth_expiry, oauth_access_token_key_id, oauth_refresh_token_key_id, oauth_extra
+) RETURNING provider_id, user_id, created_at, updated_at, oauth_access_token, oauth_refresh_token, oauth_expiry, oauth_access_token_key_id, oauth_refresh_token_key_id, oauth_extra, oauth_refresh_failure_reason
 `
 
 type InsertExternalAuthLinkParams struct {
@@ -1839,6 +1841,7 @@ func (q *sqlQuerier) InsertExternalAuthLink(ctx context.Context, arg InsertExter
 		&i.OAuthAccessTokenKeyID,
 		&i.OAuthRefreshTokenKeyID,
 		&i.OAuthExtra,
+		&i.OauthRefreshFailureReason,
 	)
 	return i, err
 }
@@ -1851,8 +1854,12 @@ UPDATE external_auth_links SET
     oauth_refresh_token = $6,
     oauth_refresh_token_key_id = $7,
     oauth_expiry = $8,
-	oauth_extra = $9
-WHERE provider_id = $1 AND user_id = $2 RETURNING provider_id, user_id, created_at, updated_at, oauth_access_token, oauth_refresh_token, oauth_expiry, oauth_access_token_key_id, oauth_refresh_token_key_id, oauth_extra
+	oauth_extra = $9,
+	-- Only 'UpdateExternalAuthLinkRefreshToken' supports updating the oauth_refresh_failure_reason.
+	-- Any updates to the external auth link, will be assumed to change the state and clear
+	-- any cached errors.
+	oauth_refresh_failure_reason = ''
+WHERE provider_id = $1 AND user_id = $2 RETURNING provider_id, user_id, created_at, updated_at, oauth_access_token, oauth_refresh_token, oauth_expiry, oauth_access_token_key_id, oauth_refresh_token_key_id, oauth_extra, oauth_refresh_failure_reason
 `
 
 type UpdateExternalAuthLinkParams struct {
@@ -1891,6 +1898,7 @@ func (q *sqlQuerier) UpdateExternalAuthLink(ctx context.Context, arg UpdateExter
 		&i.OAuthAccessTokenKeyID,
 		&i.OAuthRefreshTokenKeyID,
 		&i.OAuthExtra,
+		&i.OauthRefreshFailureReason,
 	)
 	return i, err
 }
@@ -1899,27 +1907,32 @@ const updateExternalAuthLinkRefreshToken = `-- name: UpdateExternalAuthLinkRefre
 UPDATE
 	external_auth_links
 SET
-	oauth_refresh_token = $1,
-	updated_at = $2
+	-- oauth_refresh_failure_reason can be set to cache the failure reason
+	-- for subsequent refresh attempts.
+	oauth_refresh_failure_reason = $1,
+	oauth_refresh_token = $2,
+	updated_at = $3
 WHERE
-    provider_id = $3
+    provider_id = $4
 AND
-    user_id = $4
+    user_id = $5
 AND
     -- Required for sqlc to generate a parameter for the oauth_refresh_token_key_id
-    $5 :: text = $5 :: text
+    $6 :: text = $6 :: text
 `
 
 type UpdateExternalAuthLinkRefreshTokenParams struct {
-	OAuthRefreshToken      string    `db:"oauth_refresh_token" json:"oauth_refresh_token"`
-	UpdatedAt              time.Time `db:"updated_at" json:"updated_at"`
-	ProviderID             string    `db:"provider_id" json:"provider_id"`
-	UserID                 uuid.UUID `db:"user_id" json:"user_id"`
-	OAuthRefreshTokenKeyID string    `db:"oauth_refresh_token_key_id" json:"oauth_refresh_token_key_id"`
+	OauthRefreshFailureReason string    `db:"oauth_refresh_failure_reason" json:"oauth_refresh_failure_reason"`
+	OAuthRefreshToken         string    `db:"oauth_refresh_token" json:"oauth_refresh_token"`
+	UpdatedAt                 time.Time `db:"updated_at" json:"updated_at"`
+	ProviderID                string    `db:"provider_id" json:"provider_id"`
+	UserID                    uuid.UUID `db:"user_id" json:"user_id"`
+	OAuthRefreshTokenKeyID    string    `db:"oauth_refresh_token_key_id" json:"oauth_refresh_token_key_id"`
 }
 
 func (q *sqlQuerier) UpdateExternalAuthLinkRefreshToken(ctx context.Context, arg UpdateExternalAuthLinkRefreshTokenParams) error {
 	_, err := q.db.ExecContext(ctx, updateExternalAuthLinkRefreshToken,
+		arg.OauthRefreshFailureReason,
 		arg.OAuthRefreshToken,
 		arg.UpdatedAt,
 		arg.ProviderID,
diff --git a/coderd/database/queries/externalauth.sql b/coderd/database/queries/externalauth.sql
index 4368ce56589f0..9ca5cf6f871ad 100644
--- a/coderd/database/queries/externalauth.sql
+++ b/coderd/database/queries/externalauth.sql
@@ -40,13 +40,20 @@ UPDATE external_auth_links SET
     oauth_refresh_token = $6,
     oauth_refresh_token_key_id = $7,
     oauth_expiry = $8,
-	oauth_extra = $9
+	oauth_extra = $9,
+	-- Only 'UpdateExternalAuthLinkRefreshToken' supports updating the oauth_refresh_failure_reason.
+	-- Any updates to the external auth link, will be assumed to change the state and clear
+	-- any cached errors.
+	oauth_refresh_failure_reason = ''
 WHERE provider_id = $1 AND user_id = $2 RETURNING *;
 
 -- name: UpdateExternalAuthLinkRefreshToken :exec
 UPDATE
 	external_auth_links
 SET
+	-- oauth_refresh_failure_reason can be set to cache the failure reason
+	-- for subsequent refresh attempts.
+	oauth_refresh_failure_reason = @oauth_refresh_failure_reason,
 	oauth_refresh_token = @oauth_refresh_token,
 	updated_at = @updated_at
 WHERE
diff --git a/coderd/externalauth/externalauth.go b/coderd/externalauth/externalauth.go
index 9b8b87748e784..24ebe13d03074 100644
--- a/coderd/externalauth/externalauth.go
+++ b/coderd/externalauth/externalauth.go
@@ -14,6 +14,7 @@ import (
 	"strings"
 	"time"
 
+	"github.com/dustin/go-humanize"
 	"golang.org/x/oauth2"
 	"golang.org/x/xerrors"
 
@@ -28,6 +29,13 @@ import (
 	"github.com/coder/retry"
 )
 
+const (
+	// failureReasonLimit is the maximum text length of an error to be cached to the
+	// database for a failed refresh token. In rare cases, the error could be a large
+	// HTML payload.
+	failureReasonLimit = 400
+)
+
 // Config is used for authentication for Git operations.
 type Config struct {
 	promoauth.InstrumentedOAuth2Config
@@ -121,11 +129,12 @@ func (c *Config) RefreshToken(ctx context.Context, db database.Store, externalAu
 		return externalAuthLink, InvalidTokenError("token expired, refreshing is either disabled or refreshing failed and will not be retried")
 	}
 
+	refreshToken := externalAuthLink.OAuthRefreshToken
+
 	// This is additional defensive programming. Because TokenSource is an interface,
 	// we cannot be sure that the implementation will treat an 'IsZero' time
 	// as "not-expired". The default implementation does, but a custom implementation
 	// might not. Removing the refreshToken will guarantee a refresh will fail.
-	refreshToken := externalAuthLink.OAuthRefreshToken
 	if c.NoRefresh {
 		refreshToken = ""
 	}
@@ -136,15 +145,30 @@ func (c *Config) RefreshToken(ctx context.Context, db database.Store, externalAu
 		Expiry:       externalAuthLink.OAuthExpiry,
 	}
 
+	// Note: The TokenSource(...) method will make no remote HTTP requests if the
+	// token is expired and no refresh token is set. This is important to prevent
+	// spamming the API, consuming rate limits, when the token is known to fail.
 	token, err := c.TokenSource(ctx, existingToken).Token()
 	if err != nil {
 		// TokenSource can fail for numerous reasons. If it fails because of
 		// a bad refresh token, then the refresh token is invalid, and we should
 		// get rid of it. Keeping it around will cause additional refresh
 		// attempts that will fail and cost us api rate limits.
+		//
+		// The error message is saved for debugging purposes.
 		if isFailedRefresh(existingToken, err) {
+			reason := err.Error()
+			if len(reason) > failureReasonLimit {
+				// Limit the length of the error message to prevent
+				// spamming the database with long error messages.
+				reason = reason[:failureReasonLimit]
+			}
 			dbExecErr := db.UpdateExternalAuthLinkRefreshToken(ctx, database.UpdateExternalAuthLinkRefreshTokenParams{
-				OAuthRefreshToken:      "", // It is better to clear the refresh token than to keep retrying.
+				// Adding a reason will prevent further attempts to try and refresh the token.
+				OauthRefreshFailureReason: reason,
+				// Remove the invalid refresh token so it is never used again. The cached
+				// `reason` can be used to know why this field was zeroed out.
+				OAuthRefreshToken:      "",
 				OAuthRefreshTokenKeyID: externalAuthLink.OAuthRefreshTokenKeyID.String,
 				UpdatedAt:              dbtime.Now(),
 				ProviderID:             externalAuthLink.ProviderID,
@@ -156,12 +180,28 @@ func (c *Config) RefreshToken(ctx context.Context, db database.Store, externalAu
 			}
 			// The refresh token was cleared
 			externalAuthLink.OAuthRefreshToken = ""
+			externalAuthLink.UpdatedAt = dbtime.Now()
 		}
 
 		// Unfortunately have to match exactly on the error message string.
 		// Improve the error message to account refresh tokens are deleted if
 		// invalid on our end.
+		//
+		// This error messages comes from the oauth2 package on our client side.
+		// So this check is not against a server generated error message.
+		// Error source: https://github.com/golang/oauth2/blob/master/oauth2.go#L277
 		if err.Error() == "oauth2: token expired and refresh token is not set" {
+			if externalAuthLink.OauthRefreshFailureReason != "" {
+				// A cached refresh failure error exists. So the refresh token was set, but was invalid, and zeroed out.
+				// Return this cached error for the original refresh attempt.
+				return externalAuthLink, InvalidTokenError(fmt.Sprintf("token expired and refreshing failed %s with: %s",
+					// Do not return the exact time, because then we have to know what timezone the
+					// user is in. This approximate time is good enough.
+					humanize.Time(externalAuthLink.UpdatedAt),
+					externalAuthLink.OauthRefreshFailureReason,
+				))
+			}
+
 			return externalAuthLink, InvalidTokenError("token expired, refreshing is either disabled or refreshing failed and will not be retried")
 		}
 
diff --git a/coderd/externalauth/externalauth_test.go b/coderd/externalauth/externalauth_test.go
index 81cf5aa1f21e2..484d59beabb9b 100644
--- a/coderd/externalauth/externalauth_test.go
+++ b/coderd/externalauth/externalauth_test.go
@@ -177,19 +177,25 @@ func TestRefreshToken(t *testing.T) {
 		link.OAuthExpiry = expired
 
 		// Make the failure a server internal error. Not related to the token
+		// This should be retried since this error is temporary.
 		refreshErr = &oauth2.RetrieveError{
 			Response: &http.Response{
 				StatusCode: http.StatusInternalServerError,
 			},
 			ErrorCode: "internal_error",
 		}
-		_, err := config.RefreshToken(ctx, mDB, link)
-		require.Error(t, err)
-		require.True(t, externalauth.IsInvalidTokenError(err))
-		require.Equal(t, refreshCount, 1)
+		totalRefreshes := 0
+		for i := 0; i < 3; i++ {
+			// Each loop will hit the temporary error and retry.
+			_, err := config.RefreshToken(ctx, mDB, link)
+			require.Error(t, err)
+			totalRefreshes++
+			require.True(t, externalauth.IsInvalidTokenError(err))
+			require.Equal(t, refreshCount, totalRefreshes)
+		}
 
-		// Try again with a bad refresh token error
-		// Expect DB call to remove the refresh token
+		// Try again with a bad refresh token error. This will invalidate the
+		// refresh token, and not retry again. Expect DB call to remove the refresh token
 		mDB.EXPECT().UpdateExternalAuthLinkRefreshToken(gomock.Any(), gomock.Any()).Return(nil).Times(1)
 		refreshErr = &oauth2.RetrieveError{ // github error
 			Response: &http.Response{
@@ -197,17 +203,18 @@ func TestRefreshToken(t *testing.T) {
 			},
 			ErrorCode: "bad_refresh_token",
 		}
-		_, err = config.RefreshToken(ctx, mDB, link)
+		_, err := config.RefreshToken(ctx, mDB, link)
 		require.Error(t, err)
+		totalRefreshes++
 		require.True(t, externalauth.IsInvalidTokenError(err))
-		require.Equal(t, refreshCount, 2)
+		require.Equal(t, refreshCount, totalRefreshes)
 
 		// When the refresh token is empty, no api calls should be made
 		link.OAuthRefreshToken = "" // mock'd db, so manually set the token to ''
 		_, err = config.RefreshToken(ctx, mDB, link)
 		require.Error(t, err)
 		require.True(t, externalauth.IsInvalidTokenError(err))
-		require.Equal(t, refreshCount, 2)
+		require.Equal(t, refreshCount, totalRefreshes)
 	})
 
 	// ValidateFailure tests if the token is no longer valid with a 401 response.