diff --git a/internal/cloudfoundry/initialize.go b/internal/cloudfoundry/initialize.go
index dc7f18d..2db7b29 100644
--- a/internal/cloudfoundry/initialize.go
+++ b/internal/cloudfoundry/initialize.go
@@ -43,7 +43,8 @@ func (i Initialize) Run(buildpacks []Buildpack) error {
 		if err == nil {
 			var payload struct {
 				Resources []struct {
-					Position int `json:"position"`
+					Position int    `json:"position"`
+					Stack    string `json:"stack"`
 				} `json:"resources"`
 			}
 			err = json.NewDecoder(buffer).Decode(&payload)
@@ -55,13 +56,20 @@ func (i Initialize) Run(buildpacks []Buildpack) error {
 				position = strconv.Itoa(payload.Resources[0].Position)
 			}
 
-			err = i.cli.Execute(pexec.Execution{
-				Args:   []string{"delete-buildpack", "-f", buildpack.Name},
-				Stdout: logs,
-				Stderr: logs,
-			})
-			if err != nil {
-				return fmt.Errorf("failed to delete buildpack: %s\n\nOutput:\n%s", err, logs)
+			for _, resource := range payload.Resources {
+				args := []string{"delete-buildpack", "-f", buildpack.Name}
+				if resource.Stack != "" {
+					args = append(args, "-s", resource.Stack)
+				}
+
+				err = i.cli.Execute(pexec.Execution{
+					Args:   args,
+					Stdout: logs,
+					Stderr: logs,
+				})
+				if err != nil {
+					return fmt.Errorf("failed to delete buildpack: %s\n\nOutput:\n%s", err, logs)
+				}
 			}
 		}
 
diff --git a/internal/cloudfoundry/initialize_test.go b/internal/cloudfoundry/initialize_test.go
index 067f26b..e5a24be 100644
--- a/internal/cloudfoundry/initialize_test.go
+++ b/internal/cloudfoundry/initialize_test.go
@@ -130,6 +130,83 @@ func testInitialize(t *testing.T, context spec.G, it spec.S) {
 			})
 		})
 
+		context("when a buildpack exists for multiple stacks", func() {
+			it.Before(func() {
+				executable.ExecuteCall.Stub = func(execution pexec.Execution) error {
+					executions = append(executions, execution)
+
+					args := strings.Join(execution.Args, " ")
+					switch {
+					case strings.Contains(args, "curl /v3/buildpacks?names=some-buildpack-name"):
+						fmt.Fprint(execution.Stdout, `{"resources":[{"position": 123, "stack": "cflinuxfs4"}, {"position": 456, "stack": "cflinuxfs5"}]}`)
+					}
+
+					return nil
+				}
+			})
+
+			it("deletes each stack-specific buildpack before re-creating", func() {
+				err := initialize.Run([]cloudfoundry.Buildpack{
+					{
+						Name: "some-buildpack-name",
+						URI:  "some-buildpack-uri",
+					},
+				})
+				Expect(err).NotTo(HaveOccurred())
+
+				Expect(executions).To(HaveLen(4))
+				Expect(executions[0]).To(MatchFields(IgnoreExtras, Fields{
+					"Args": Equal([]string{"curl", "/v3/buildpacks?names=some-buildpack-name"}),
+				}))
+				Expect(executions[1]).To(MatchFields(IgnoreExtras, Fields{
+					"Args": Equal([]string{"delete-buildpack", "-f", "some-buildpack-name", "-s", "cflinuxfs4"}),
+				}))
+				Expect(executions[2]).To(MatchFields(IgnoreExtras, Fields{
+					"Args": Equal([]string{"delete-buildpack", "-f", "some-buildpack-name", "-s", "cflinuxfs5"}),
+				}))
+				Expect(executions[3]).To(MatchFields(IgnoreExtras, Fields{
+					"Args": Equal([]string{"create-buildpack", "some-buildpack-name", "some-buildpack-uri", "123"}),
+				}))
+			})
+		})
+
+		context("when a buildpack exists with a single stack", func() {
+			it.Before(func() {
+				executable.ExecuteCall.Stub = func(execution pexec.Execution) error {
+					executions = append(executions, execution)
+
+					args := strings.Join(execution.Args, " ")
+					switch {
+					case strings.Contains(args, "curl /v3/buildpacks?names=some-buildpack-name"):
+						fmt.Fprint(execution.Stdout, `{"resources":[{"position": 123, "stack": "cflinuxfs4"}]}`)
+					}
+
+					return nil
+				}
+			})
+
+			it("deletes the buildpack with the stack flag", func() {
+				err := initialize.Run([]cloudfoundry.Buildpack{
+					{
+						Name: "some-buildpack-name",
+						URI:  "some-buildpack-uri",
+					},
+				})
+				Expect(err).NotTo(HaveOccurred())
+
+				Expect(executions).To(HaveLen(3))
+				Expect(executions[0]).To(MatchFields(IgnoreExtras, Fields{
+					"Args": Equal([]string{"curl", "/v3/buildpacks?names=some-buildpack-name"}),
+				}))
+				Expect(executions[1]).To(MatchFields(IgnoreExtras, Fields{
+					"Args": Equal([]string{"delete-buildpack", "-f", "some-buildpack-name", "-s", "cflinuxfs4"}),
+				}))
+				Expect(executions[2]).To(MatchFields(IgnoreExtras, Fields{
+					"Args": Equal([]string{"create-buildpack", "some-buildpack-name", "some-buildpack-uri", "123"}),
+				}))
+			})
+		})
+
 		context("failure cases", func() {
 			context("when the buildpack JSON cannot be parsed", func() {
 				it.Before(func() {
@@ -170,7 +247,7 @@ func testInitialize(t *testing.T, context spec.G, it spec.S) {
 						args := strings.Join(execution.Args, " ")
 						switch {
 						case strings.Contains(args, "curl /v3/buildpacks?names=some-buildpack-name"):
-							fmt.Fprintln(execution.Stdout, "{}")
+							fmt.Fprintln(execution.Stdout, `{"resources":[{"position": 123}]}`)
 
 						case strings.Contains(args, "delete-buildpack -f some-buildpack-name"):
 							fmt.Fprintln(execution.Stderr, "something bad happened")
@@ -192,7 +269,8 @@ func testInitialize(t *testing.T, context spec.G, it spec.S) {
 							URI:  "other-buildpack-uri",
 						},
 					})
-					Expect(err).To(MatchError("failed to delete buildpack: delete-buildpack failed\n\nOutput:\n{}\nsomething bad happened\n"))
+					Expect(err).To(MatchError(ContainSubstring("failed to delete buildpack: delete-buildpack failed")))
+					Expect(err).To(MatchError(ContainSubstring("something bad happened")))
 				})
 			})