diff --git a/pkg/skaffold/schema/profiles.go b/pkg/skaffold/schema/profiles.go
index feaec4eea19..9fd467b4dec 100644
--- a/pkg/skaffold/schema/profiles.go
+++ b/pkg/skaffold/schema/profiles.go
@@ -105,6 +105,7 @@ func activatedProfiles(profiles []latest.Profile, opts cfg.SkaffoldOptions) ([]s
 						contextSpecificProfiles = append(contextSpecificProfiles, profile.Name)
 					}
 					activated = append(activated, profile.Name)
+					break
 				}
 			}
 		}
@@ -113,7 +114,7 @@ func activatedProfiles(profiles []latest.Profile, opts cfg.SkaffoldOptions) ([]s
 	for _, profile := range opts.Profiles {
 		if strings.HasPrefix(profile, "-") {
 			activated = removeValue(activated, strings.TrimPrefix(profile, "-"))
-		} else {
+		} else if !skutil.StrSliceContains(activated, profile) {
 			activated = append(activated, profile)
 		}
 	}
diff --git a/pkg/skaffold/schema/profiles_test.go b/pkg/skaffold/schema/profiles_test.go
index 1705458f032..bcafd189935 100644
--- a/pkg/skaffold/schema/profiles_test.go
+++ b/pkg/skaffold/schema/profiles_test.go
@@ -555,6 +555,20 @@ func TestActivatedProfiles(t *testing.T) {
 				{Name: "regex-activated-substring-match", Activation: []latest.Activation{{Env: "KEY=^VAL"}}},
 			},
 			expected: []string{"activated", "also-activated", "regex-activated", "regex-activated-two", "regex-activated-substring-match"},
+		}, {
+			description: "Profile with multiple valid activations",
+			envs:        map[string]string{"KEY": "VALUE"},
+			opts: cfg.SkaffoldOptions{
+				ProfileAutoActivation: true,
+				Command:               "dev",
+				Profiles:              []string{"activated", "also-activated"},
+			},
+			profiles: []latest.Profile{
+				{Name: "activated", Activation: []latest.Activation{{Env: "KEY=VALUE"}, {Command: "dev"}}},
+				{Name: "not-activated", Activation: []latest.Activation{{Env: "KEY=OTHER"}}},
+				{Name: "also-activated", Activation: []latest.Activation{{Env: "KEY=!OTHER"}}},
+			},
+			expected: []string{"activated", "also-activated"},
 		}, {
 			description: "Invalid env variable",
 			envs:        map[string]string{"KEY": "VALUE"},