diff --git a/frappe/www/update-password.html b/frappe/www/update-password.html
index 7351311def..2e6c3cf089 100644
--- a/frappe/www/update-password.html
+++ b/frappe/www/update-password.html
@@ -23,10 +23,10 @@
 				<input id="confirm_password" type="password"
 					class="form-control" placeholder="{{ _('Confirm Password') }}" autocomplete="new-password">
 
-				<p class="password-mismatch-message text-muted small hidden mt-2"></p>
 			</div>
-			<p class='password-strength-message text-muted small hidden'></p>
-			<button type="submit" id="update"
+			<p class="password-mismatch-message text-muted small hidden mt-2"></p>
+			<p class='password-strength-message text-muted small mt-2 hidden'></p>
+			<button type="submit" id="update" disabled = true style="cursor: not-allowed;"
 				class="btn btn-primary btn-block btn-update">{{_("Confirm")}}</button>
 		</form>
 		{%- if not disable_signup -%}
@@ -43,11 +43,27 @@
 <script>
 
 frappe.ready(function() {
-	if(frappe.utils.get_url_arg("key")) {
-		$("#old_password").parent().toggle();
+	// URL args
+	const key = frappe.utils.get_url_arg('key');
+	const password_expired = frappe.utils.get_url_arg('password_expired');
+	// inputs, paragraphs and button elements
+	const old_password = $('#old_password');
+	const new_password = $('#new_password');
+	const confirm_password = $('#confirm_password');
+	const update_button = $('#update');
+	const password_strength_indicator = $('.password-strength-indicator');
+	const password_strength_message =$('.password-strength-message');
+	const password_mismatch_message = $('.password-mismatch-message');
+	// Info text
+	const password_not_same_as_old_password = "{{ _('New password cannot be same as old password') }}";
+	const password_mismatch = "{{ _('Passwords do not match') }}";
+	const password_strength_message_success = "{{ _('Success! You are good to go 👍') }}";
+
+	if(key) {
+		old_password.parent().toggle();
 	}
 
-	if(frappe.utils.get_url_arg("password_expired")) {
+	if(password_expired) {
 		$(".password-box").html("{{ _('The password of your account has expired.') }}");
 	}
 
@@ -55,18 +71,18 @@ frappe.ready(function() {
 		return false;
 	});
 
-	$("#new_password").on("keypress", function(e) {
-		if(e.which===13) $("#update").click();
+	new_password.on("keypress", function(e) {
+		if(e.which===13) update_button.click();
 	})
 
-	$("#update").click(function() {
+	update_button.click(function() {
 		var args = {
-			key: frappe.utils.get_url_arg("key") || "",
-			old_password: $("#old_password").val(),
-			new_password: $("#new_password").val(),
+			key: key || "",
+			old_password: old_password.val(),
+			new_password: new_password.val(),
+			confirm_password: confirm_password.val(),
 			logout_all_sessions: 1
 		}
-		const confirm_password = $('#confirm_password').val()
 		if (!args.old_password && !args.key) {
 			frappe.msgprint({
 				title: "{{ _('Missing Value') }}",
@@ -81,20 +97,36 @@ frappe.ready(function() {
 				clear: true
 			});
 		}
-		if (args.new_password !== confirm_password) {
-			$('.password-mismatch-message').text("{{ _('Passwords do not match') }}")
+		if (args.old_password === args.new_password) {
+			frappe.msgprint({
+				title: "{{ _('Invalid Password') }}",
+				message: password_not_same_as_old_password,
+			});
+			password_strength_message.addClass('hidden');
+			return;
+		}
+
+		if (args.new_password !== args.confirm_password) {
+			password_mismatch_message.text(password_mismatch)
 				.removeClass('hidden text-muted').addClass('text-danger');
-			return false;
+			password_strength_message.addClass('hidden');
+			return;
 		}
 
 		frappe.call({
 			type: "POST",
 			method: "frappe.core.doctype.user.user.update_password",
-			btn: $("#update"),
+			btn: update_button,
 			args: args,
 			statusCode: {
 				401: function() {
 					$(".page-card-head .reset-password-heading").text("{{ _('Invalid Password') }}");
+					frappe.msgprint({
+						title: "{{ _('Invalid Password') }}",
+						message: "{{ _('Your old password is incorrect.') }}",
+						// clear any server message
+						clear: true
+					});
 				},
 				410: function({ responseJSON }) {
 					const title = "{{ _('Invalid Link') }}";
@@ -127,21 +159,55 @@ frappe.ready(function() {
 		return false;
 	});
 
-	window.strength_indicator = $('.password-strength-indicator');
-	window.strength_message = $('.password-strength-message');
+	window.strength_indicator = password_strength_indicator;
+	window.strength_message = password_strength_message;
 
-	$('#new_password').on('keyup', function() {
+	new_password.on('keyup', function() {
 		window.clear_timeout();
 		window.timout_password_strength = setTimeout(window.test_password_strength, 200);
 	});
 
+	$("#old_password, #new_password, #confirm_password").on("keyup", frappe.utils.debounce(function () {
+		let common_conditions = new_password.val() && confirm_password.val() && new_password.val() === confirm_password.val() &&
+		password_strength_message.text() === password_strength_message_success
+
+		if (new_password.val() && old_password.val() === new_password.val()) {
+			password_mismatch_message.text(password_not_same_as_old_password)
+				.removeClass("hidden text-muted").addClass("text-danger");
+
+			password_strength_message.addClass("hidden");
+		}
+		if ((new_password.val() || old_password.val) && old_password.val() !== new_password.val()) {
+			password_mismatch_message.addClass("hidden");
+			password_strength_message.removeClass("hidden");
+			password_mismatch_message.text('')
+		}
+
+		if (new_password.val() === confirm_password.val() && old_password.val() !== new_password.val() ) {
+			password_mismatch_message.addClass("hidden");
+			password_strength_message.removeClass("hidden");
+		}
+		if (confirm_password.val() &&  new_password.val() !== confirm_password.val()) {
+			password_mismatch_message.text(password_mismatch)
+				.removeClass("hidden text-muted").addClass("text-danger");
+			password_strength_message.addClass("hidden");
+		}
+		if ((key || (!key && old_password.val() && password_mismatch_message.text() !== password_not_same_as_old_password )) && common_conditions ) {
+			update_button.prop("disabled", false).css("cursor", "pointer");
+		}
+		else {
+			update_button.prop("disabled", true).css("cursor", "not-allowed");
+		}
+		},500)
+	)
+
 	window.test_password_strength = function() {
 		window.timout_password_strength = null;
 
 		var args = {
-			key: frappe.utils.get_url_arg("key") || "",
-			old_password: $("#old_password").val(),
-			new_password: $("#new_password").val()
+			key: key || "",
+			old_password: old_password.val(),
+			new_password: new_password.val()
 		}
 
 		if (!args.new_password) {
@@ -195,9 +261,11 @@ frappe.ready(function() {
 				message.push(feedback.help_msg);
 
 			} else {
-				message.push("{{ _('Success! You are good to go 👍') }}");
+				message.push(password_strength_message_success);
 			}
 		}
+		password_mismatch_message.addClass('hidden');
+
 		strength_message.html(message.join(' ') || '').removeClass('hidden');
 	}