diff --git a/internal/k8s/validation.go b/internal/k8s/validation.go
index 4899a4a024..48df215cdd 100644
--- a/internal/k8s/validation.go
+++ b/internal/k8s/validation.go
@@ -67,16 +67,19 @@ const (
 	commaDelimiter     = ","
 	annotationValueFmt = `([^"$\\]|\\[^$])*`
 	pathFmt            = `/[^\s{};]*`
+	jwtTokenValueFmt   = "\\$" + annotationValueFmt
 )
 
 const (
 	annotationValueFmtErrMsg = `a valid annotation value must have all '"' escaped and must not contain any '$' or end with an unescaped '\'`
 	pathErrMsg               = "must start with / and must not include any whitespace character, `{`, `}` or `;`"
+	jwtTokenValueFmtErrMsg   = `a valid annotation value must start with '$', have all '"' escaped, and must not contain any '$' or end with an unescaped '\'`
 )
 
 var (
-	validAnnotationValueRegex = regexp.MustCompile("^" + annotationValueFmt + "$")
-	pathRegexp                = regexp.MustCompile("^" + pathFmt + "$")
+	pathRegexp                        = regexp.MustCompile("^" + pathFmt + "$")
+	validAnnotationValueRegex         = regexp.MustCompile("^" + annotationValueFmt + "$")
+	validJWTTokenAnnotationValueRegex = regexp.MustCompile("^" + jwtTokenValueFmt + "$")
 )
 
 type annotationValidationContext struct {
@@ -222,6 +225,7 @@ var (
 		},
 		jwtTokenAnnotation: {
 			validatePlusOnlyAnnotation,
+			validateJWTTokenAnnotation,
 		},
 		jwtLoginURLAnnotation: {
 			validatePlusOnlyAnnotation,
@@ -339,6 +343,17 @@ func validateJWTRealm(context *annotationValidationContext) field.ErrorList {
 	return allErrs
 }
 
+func validateJWTTokenAnnotation(context *annotationValidationContext) field.ErrorList {
+	allErrs := field.ErrorList{}
+
+	if !validJWTTokenAnnotationValueRegex.MatchString(context.value) {
+		msg := validation.RegexError(jwtTokenValueFmtErrMsg, jwtTokenValueFmt, "$http_token", "$cookie_auth_token")
+		allErrs = append(allErrs, field.Invalid(context.fieldPath, context.value, msg))
+	}
+
+	return allErrs
+}
+
 func validateHTTPHeadersAnnotation(context *annotationValidationContext) field.ErrorList {
 	var allErrs field.ErrorList
 	headers := strings.Split(context.value, commaDelimiter)
diff --git a/internal/k8s/validation_test.go b/internal/k8s/validation_test.go
index a131b05df6..a53c4c629f 100644
--- a/internal/k8s/validation_test.go
+++ b/internal/k8s/validation_test.go
@@ -1499,6 +1499,75 @@ func TestValidateNginxIngressAnnotations(t *testing.T) {
 			expectedErrors:        nil,
 			msg:                   "valid nginx.com/jwt-token annotation",
 		},
+		{
+			annotations: map[string]string{
+				"nginx.com/jwt-token": "cookie_auth_token",
+			},
+			specServices:          map[string]bool{},
+			isPlus:                true,
+			appProtectEnabled:     false,
+			appProtectDosEnabled:  false,
+			internalRoutesEnabled: false,
+			expectedErrors: []string{
+				"annotations.nginx.com/jwt-token: Invalid value: \"cookie_auth_token\": a valid annotation value must start with '$', have all '\"' escaped, and must not contain any '$' or end with an unescaped '\\' (e.g. '$http_token',  or '$cookie_auth_token', regex used for validation is '\\$([^\"$\\\\]|\\\\[^$])*')",
+			}, msg: "invalid nginx.com/jwt-token annotation, '$' missing",
+		},
+		{
+			annotations: map[string]string{
+				"nginx.com/jwt-token": `$cookie_auth_token"`,
+			},
+			specServices:          map[string]bool{},
+			isPlus:                true,
+			appProtectEnabled:     false,
+			appProtectDosEnabled:  false,
+			internalRoutesEnabled: false,
+			expectedErrors: []string{
+				"annotations.nginx.com/jwt-token: Invalid value: \"$cookie_auth_token\\\"\": a valid annotation value must start with '$', have all '\"' escaped, and must not contain any '$' or end with an unescaped '\\' (e.g. '$http_token',  or '$cookie_auth_token', regex used for validation is '\\$([^\"$\\\\]|\\\\[^$])*')",
+			},
+			msg: "invalid nginx.com/jwt-token annotation, containing unescaped '\"'",
+		},
+		{
+			annotations: map[string]string{
+				"nginx.com/jwt-token": `$cookie_auth_token\`,
+			},
+			specServices:          map[string]bool{},
+			isPlus:                true,
+			appProtectEnabled:     false,
+			appProtectDosEnabled:  false,
+			internalRoutesEnabled: false,
+			expectedErrors: []string{
+				"annotations.nginx.com/jwt-token: Invalid value: \"$cookie_auth_token\\\\\": a valid annotation value must start with '$', have all '\"' escaped, and must not contain any '$' or end with an unescaped '\\' (e.g. '$http_token',  or '$cookie_auth_token', regex used for validation is '\\$([^\"$\\\\]|\\\\[^$])*')",
+			},
+			msg: "invalid nginx.com/jwt-token annotation, containing escape characters",
+		},
+		{
+			annotations: map[string]string{
+				"nginx.com/jwt-token": "cookie_auth$token",
+			},
+			specServices:          map[string]bool{},
+			isPlus:                true,
+			appProtectEnabled:     false,
+			appProtectDosEnabled:  false,
+			internalRoutesEnabled: false,
+			expectedErrors: []string{
+				"annotations.nginx.com/jwt-token: Invalid value: \"cookie_auth$token\": a valid annotation value must start with '$', have all '\"' escaped, and must not contain any '$' or end with an unescaped '\\' (e.g. '$http_token',  or '$cookie_auth_token', regex used for validation is '\\$([^\"$\\\\]|\\\\[^$])*')",
+			},
+			msg: "invalid nginx.com/jwt-token annotation, containing incorrect variable",
+		},
+		{
+			annotations: map[string]string{
+				"nginx.com/jwt-token": "$cookie_auth_token$http_token",
+			},
+			specServices:          map[string]bool{},
+			isPlus:                true,
+			appProtectEnabled:     false,
+			appProtectDosEnabled:  false,
+			internalRoutesEnabled: false,
+			expectedErrors: []string{
+				"annotations.nginx.com/jwt-token: Invalid value: \"$cookie_auth_token$http_token\": a valid annotation value must start with '$', have all '\"' escaped, and must not contain any '$' or end with an unescaped '\\' (e.g. '$http_token',  or '$cookie_auth_token', regex used for validation is '\\$([^\"$\\\\]|\\\\[^$])*')",
+			},
+			msg: "invalid nginx.com/jwt-token annotation, containing more than 1 variable",
+		},
 
 		{
 			annotations: map[string]string{