diff --git a/zendesk/attachment.go b/zendesk/attachment.go
index adf2062c..6166a453 100644
--- a/zendesk/attachment.go
+++ b/zendesk/attachment.go
@@ -71,7 +71,7 @@ func (wr *writer) open() error {
 		return err
 	}
 
-	wr.prepareRequest(wr.ctx, req)
+	req = wr.prepareRequest(wr.ctx, req)
 	req.Header.Set("Content-Type", "application/binary")
 
 	q := req.URL.Query()
diff --git a/zendesk/attachment_test.go b/zendesk/attachment_test.go
index 9c69db77..812d8f47 100644
--- a/zendesk/attachment_test.go
+++ b/zendesk/attachment_test.go
@@ -2,6 +2,7 @@ package zendesk
 
 import (
 	"bytes"
+	"context"
 	"crypto/sha1"
 	"io"
 	"net/http"
@@ -12,7 +13,7 @@ import (
 )
 
 func TestWrite(t *testing.T) {
-	file := readFixture(filepath.Join("POST", "upload.json"))
+	file := readFixture(filepath.Join(http.MethodPost, "upload.json"))
 	h := sha1.New()
 	h.Write(file)
 	expectedSum := h.Sum(nil)
@@ -49,6 +50,30 @@ func TestWrite(t *testing.T) {
 	}
 }
 
+func TestWriteCancelledContext(t *testing.T) {
+	mockAPI := newMockAPIWithStatus(http.MethodPost, "ticket.json",  201)
+	defer mockAPI.Close()
+
+	client := newTestClient(mockAPI)
+
+	canceled, cancelFunc := context.WithCancel(ctx)
+	cancelFunc()
+	w := client.UploadAttachment(canceled, "foo", "bar")
+
+	file := []byte("body")
+	r := bytes.NewBuffer(file)
+
+	_, err := io.Copy(w, r)
+	if err == nil {
+		t.Fatalf("did not recieve expected error")
+	}
+
+	_, err = w.Close()
+	if err == nil {
+		t.Fatal("Did not receive error when closing writer")
+	}
+}
+
 func TestDeleteUpload(t *testing.T) {
 	mockAPI := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		w.WriteHeader(http.StatusNoContent)
@@ -62,6 +87,22 @@ func TestDeleteUpload(t *testing.T) {
 	}
 }
 
+func TestDeleteUploadCanceledContext(t *testing.T) {
+	mockAPI := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusNoContent)
+		w.Write(nil)
+	}))
+
+	c := newTestClient(mockAPI)
+	canceled, cancelFunc := context.WithCancel(ctx)
+	cancelFunc()
+
+	err := c.DeleteUpload(canceled, "foobar")
+	if err == nil {
+		t.Fatal("did not get expected error")
+	}
+}
+
 func TestGetAttachment(t *testing.T) {
 	mockAPI := newMockAPI(http.MethodGet, "attachment.json")
 	client := newTestClient(mockAPI)
diff --git a/zendesk/brand_test.go b/zendesk/brand_test.go
index a3cdfffe..b7ac3127 100644
--- a/zendesk/brand_test.go
+++ b/zendesk/brand_test.go
@@ -1,6 +1,7 @@
 package zendesk
 
 import (
+	"context"
 	"net/http"
 	"net/http/httptest"
 	"testing"
@@ -17,6 +18,20 @@ func TestCreateBrand(t *testing.T) {
 	}
 }
 
+func TestCreateBrandCanceledContext(t *testing.T) {
+	mockAPI := newMockAPIWithStatus(http.MethodPost, "brands.json", http.StatusCreated)
+	client := newTestClient(mockAPI)
+	defer mockAPI.Close()
+
+	canceled, cancelFunc := context.WithCancel(ctx)
+	cancelFunc()
+
+	_, err := client.CreateBrand(canceled, Brand{})
+	if err == nil {
+		t.Fatalf("did not get expected error")
+	}
+}
+
 func TestGetBrand(t *testing.T) {
 	mockAPI := newMockAPI(http.MethodGet, "brand.json")
 	client := newTestClient(mockAPI)
@@ -49,6 +64,19 @@ func TestUpdateBrand(t *testing.T) {
 	}
 }
 
+func TestUpdateBrandCanceledContext(t *testing.T) {
+	mockAPI := newMockAPIWithStatus(http.MethodPut, "brands.json", http.StatusOK)
+	client := newTestClient(mockAPI)
+	defer mockAPI.Close()
+
+	canceled, cancelFunc := context.WithCancel(ctx)
+	cancelFunc()
+	_, err := client.UpdateBrand(canceled, int64(1234), Brand{})
+	if err == nil {
+		t.Fatalf("did not get expected error")
+	}
+}
+
 func TestDeleteBrand(t *testing.T) {
 	mockAPI := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		w.WriteHeader(http.StatusNoContent)
diff --git a/zendesk/ticket_test.go b/zendesk/ticket_test.go
index d2d4ce82..2bff88e4 100644
--- a/zendesk/ticket_test.go
+++ b/zendesk/ticket_test.go
@@ -1,6 +1,7 @@
 package zendesk
 
 import (
+	"context"
 	"encoding/json"
 	"net/http"
 	"sort"
@@ -46,6 +47,18 @@ func TestGetTicket(t *testing.T) {
 	}
 }
 
+func TestGetTicketCanceledContext(t *testing.T) {
+	mockAPI := newMockAPI(http.MethodGet, "ticket.json")
+	client := newTestClient(mockAPI)
+	defer mockAPI.Close()
+	canceled, cancelFunc := context.WithCancel(ctx)
+	cancelFunc()
+	_, err := client.GetTicket(canceled, 2)
+	if err == nil {
+		t.Fatal("Did not get error when calling with cancelled context")
+	}
+}
+
 // Test the CustomField unmarshalling fails on an invalid value.
 // In this case a float64 as CustomField.Value should cause an error.
 func TestGetTicketWithInvalidCustomField(t *testing.T) {
diff --git a/zendesk/zendesk.go b/zendesk/zendesk.go
index 264ac4f2..33ee3915 100644
--- a/zendesk/zendesk.go
+++ b/zendesk/zendesk.go
@@ -90,7 +90,7 @@ func (z *Client) get(ctx context.Context, path string) ([]byte, error) {
 		return nil, err
 	}
 
-	z.prepareRequest(ctx, req)
+	req = z.prepareRequest(ctx, req)
 
 	resp, err := z.httpClient.Do(req)
 	if err != nil {
@@ -123,7 +123,8 @@ func (z *Client) post(ctx context.Context, path string, data interface{}) ([]byt
 	if err != nil {
 		return nil, err
 	}
-	z.prepareRequest(ctx, req)
+
+	req = z.prepareRequest(ctx, req)
 
 	resp, err := z.httpClient.Do(req)
 	if err != nil {
@@ -157,7 +158,8 @@ func (z *Client) put(ctx context.Context, path string, data interface{}) ([]byte
 	if err != nil {
 		return nil, err
 	}
-	z.prepareRequest(ctx, req)
+
+	req = z.prepareRequest(ctx, req)
 
 	resp, err := z.httpClient.Do(req)
 	if err != nil {
@@ -186,7 +188,8 @@ func (z *Client) delete(ctx context.Context, path string) error {
 	if err != nil {
 		return err
 	}
-	z.prepareRequest(ctx, req)
+
+	req = z.prepareRequest(ctx, req)
 
 	resp, err := z.httpClient.Do(req)
 	if err != nil {
@@ -210,10 +213,12 @@ func (z *Client) delete(ctx context.Context, path string) error {
 }
 
 // prepare request sets common request variables such as authn and user agent
-func (z *Client) prepareRequest(ctx context.Context, req *http.Request) {
-	req = req.WithContext(ctx)
-	z.includeHeaders(req)
-	req.SetBasicAuth(z.credential.Email(), z.credential.Secret())
+func (z *Client) prepareRequest(ctx context.Context, req *http.Request) *http.Request {
+	out := req.WithContext(ctx)
+	z.includeHeaders(out)
+	out.SetBasicAuth(z.credential.Email(), z.credential.Secret())
+
+	return out
 }
 
 // includeHeaders set HTTP headers from client.headers to *http.Request