diff --git a/stackit/internal/core/retry_round_tripper.go b/stackit/internal/core/retry_round_tripper.go
new file mode 100644
index 00000000..8495b803
--- /dev/null
+++ b/stackit/internal/core/retry_round_tripper.go
@@ -0,0 +1,241 @@
+package core
+
+import (
+	"context"
+	"crypto/rand"
+	"errors"
+	"fmt"
+	"math/big"
+	"net/http"
+	"time"
+
+	"github.com/hashicorp/terraform-plugin-log/tflog"
+)
+
+const (
+	// backoffMultiplier is the factor by which the delay is multiplied for exponential backoff.
+	backoffMultiplier = 2
+	// jitterFactor is the divisor used to calculate jitter (e.g., half of the base delay).
+	jitterFactor = 2
+)
+
+var (
+	// ErrRequestFailedAfterRetries is returned when a request fails after all retry attempts.
+	ErrRequestFailedAfterRetries = errors.New("request failed after all retry attempts")
+)
+
+// RetryRoundTripper implements an http.RoundTripper that adds automatic retry logic for failed requests.
+type RetryRoundTripper struct {
+	next          http.RoundTripper
+	maxRetries    int
+	delay         time.Duration
+	initialDelay  time.Duration
+	maxDelay      time.Duration
+	perTryTimeout time.Duration
+}
+
+// NewRetryRoundTripper creates a new instance of the RetryRoundTripper with the specified configuration.
+func NewRetryRoundTripper(
+	next http.RoundTripper,
+	maxRetries int,
+	initialDelay, delay, maxDelay, perTryTimeout time.Duration,
+) *RetryRoundTripper {
+	return &RetryRoundTripper{
+		next:          next,
+		maxRetries:    maxRetries,
+		initialDelay:  initialDelay,
+		delay:         delay,
+		maxDelay:      maxDelay,
+		perTryTimeout: perTryTimeout,
+	}
+}
+
+// RoundTrip executes the request and retries on failure.
+func (rrt *RetryRoundTripper) RoundTrip(req *http.Request) (*http.Response, error) {
+	resp, err := rrt.executeRequest(req)
+	if !rrt.shouldRetry(resp, err) {
+		if err != nil {
+			return resp, fmt.Errorf("initial request failed, not retrying: %w", err)
+		}
+
+		return resp, nil
+	}
+
+	return rrt.retryLoop(req, resp, err)
+}
+
+// executeRequest performs a single HTTP request with a per-try timeout.
+func (rrt *RetryRoundTripper) executeRequest(req *http.Request) (*http.Response, error) {
+	ctx, cancel := context.WithTimeout(req.Context(), rrt.perTryTimeout)
+	defer cancel()
+
+	resp, err := rrt.next.RoundTrip(req.WithContext(ctx))
+	if err != nil {
+		if errors.Is(err, context.DeadlineExceeded) {
+			return resp, fmt.Errorf("per-try timeout of %v exceeded: %w", rrt.perTryTimeout, err)
+		}
+
+		return resp, fmt.Errorf("http roundtrip failed: %w", err)
+	}
+
+	return resp, nil
+}
+
+// retryLoop handles the retry logic for a failed request.
+func (rrt *RetryRoundTripper) retryLoop(
+	req *http.Request,
+	initialResp *http.Response,
+	initialErr error,
+) (*http.Response, error) {
+	var (
+		lastErr      = initialErr
+		resp         = initialResp
+		currentDelay = rrt.initialDelay
+	)
+
+	ctx := req.Context()
+
+	for attempt := 1; attempt <= rrt.maxRetries; attempt++ {
+		rrt.logRetryAttempt(ctx, attempt, currentDelay, lastErr)
+
+		waitDuration := rrt.calculateWaitDurationWithJitter(ctx, currentDelay)
+		if err := rrt.waitForDelay(ctx, waitDuration); err != nil {
+			return nil, err // Context was cancelled during wait.
+		}
+
+		// Exponential backoff for the next potential retry.
+		currentDelay = rrt.updateCurrentDelay(currentDelay)
+
+		// Retry attempt.
+		resp, lastErr = rrt.executeRequest(req)
+		if !rrt.shouldRetry(resp, lastErr) {
+			if lastErr != nil {
+				return resp, fmt.Errorf("request failed on retry attempt %d: %w", attempt, lastErr)
+			}
+
+			return resp, nil
+		}
+	}
+
+	return nil, rrt.handleFinalError(ctx, resp, lastErr)
+}
+
+// logRetryAttempt logs the details of a retry attempt.
+func (rrt *RetryRoundTripper) logRetryAttempt(
+	ctx context.Context,
+	attempt int,
+	delay time.Duration,
+	err error,
+) {
+	tflog.Info(
+		ctx, "Request failed, retrying...", map[string]interface{}{
+			"attempt":      attempt,
+			"max_attempts": rrt.maxRetries,
+			"delay":        delay,
+			"error":        err.Error(),
+		},
+	)
+}
+
+// updateCurrentDelay calculates the next delay for exponential backoff.
+func (rrt *RetryRoundTripper) updateCurrentDelay(currentDelay time.Duration) time.Duration {
+	currentDelay *= backoffMultiplier
+	if currentDelay > rrt.maxDelay {
+		return rrt.maxDelay
+	}
+
+	return currentDelay
+}
+
+// handleFinalError constructs and returns the final error after all retries have been exhausted.
+func (rrt *RetryRoundTripper) handleFinalError(
+	ctx context.Context,
+	resp *http.Response,
+	lastErr error,
+) error {
+	if resp != nil {
+		if err := resp.Body.Close(); err != nil {
+
+			tflog.Warn(
+				ctx, "Failed to close response body", map[string]interface{}{
+					"error": err.Error(),
+				},
+			)
+		}
+	}
+
+	if lastErr != nil {
+		return fmt.Errorf("%w: %w", ErrRequestFailedAfterRetries, lastErr)
+	}
+
+	// This case occurs if shouldRetry was true due to a retryable status code,
+	// but all retries failed with similar status codes.
+	if resp != nil {
+		return fmt.Errorf(
+			"%w: last retry attempt failed with status code %d",
+			ErrRequestFailedAfterRetries,
+			resp.StatusCode,
+		)
+	}
+
+	return fmt.Errorf("%w: no response received", ErrRequestFailedAfterRetries)
+}
+
+// shouldRetry determines if a request should be retried based on the response or an error.
+func (rrt *RetryRoundTripper) shouldRetry(resp *http.Response, err error) bool {
+	if err != nil {
+		return true
+	}
+
+	if resp != nil {
+		if resp.StatusCode == http.StatusBadGateway ||
+			resp.StatusCode == http.StatusServiceUnavailable ||
+			resp.StatusCode == http.StatusGatewayTimeout {
+			return true
+		}
+	}
+
+	return false
+
+}
+
+// calculateWaitDurationWithJitter calculates the backoff duration for the next retry,
+// adding a random jitter to prevent thundering herd issues.
+func (rrt *RetryRoundTripper) calculateWaitDurationWithJitter(
+	ctx context.Context,
+	baseDelay time.Duration,
+) time.Duration {
+	if baseDelay <= 0 {
+		return 0
+	}
+
+	maxJitter := int64(baseDelay / jitterFactor)
+	if maxJitter <= 0 {
+		return baseDelay
+	}
+
+	random, err := rand.Int(rand.Reader, big.NewInt(maxJitter))
+	if err != nil {
+		tflog.Warn(
+			ctx, "Failed to generate random jitter, proceeding without it.", map[string]interface{}{
+				"error": err.Error(),
+			},
+		)
+
+		return baseDelay
+	}
+
+	jitter := time.Duration(random.Int64())
+
+	return baseDelay + jitter
+}
+
+// waitForDelay pauses execution for a given duration or until the context is canceled.
+func (rrt *RetryRoundTripper) waitForDelay(ctx context.Context, delay time.Duration) error {
+	select {
+	case <-ctx.Done():
+		return fmt.Errorf("context cancelled during backoff wait: %w", ctx.Err())
+	case <-time.After(delay):
+		return nil
+	}
+}