diff --git a/erpnext/erpnext_integrations/doctype/taxjar_settings/__init__.py b/erpnext/erpnext_integrations/doctype/taxjar_settings/__init__.py
new file mode 100644
index 0000000..e69de29
--- /dev/null
+++ b/erpnext/erpnext_integrations/doctype/taxjar_settings/__init__.py
diff --git a/erpnext/erpnext_integrations/doctype/taxjar_settings/taxjar_settings.js b/erpnext/erpnext_integrations/doctype/taxjar_settings/taxjar_settings.js
new file mode 100644
index 0000000..62d5709
--- /dev/null
+++ b/erpnext/erpnext_integrations/doctype/taxjar_settings/taxjar_settings.js
@@ -0,0 +1,9 @@
+// Copyright (c) 2020, Frappe Technologies Pvt. Ltd. and contributors
+// For license information, please see license.txt
+
+frappe.ui.form.on('TaxJar Settings', {
+	is_sandbox: (frm) => {
+		frm.toggle_reqd("api_key", !frm.doc.is_sandbox);
+		frm.toggle_reqd("sandbox_api_key", frm.doc.is_sandbox);
+	}
+});
diff --git a/erpnext/erpnext_integrations/doctype/taxjar_settings/taxjar_settings.json b/erpnext/erpnext_integrations/doctype/taxjar_settings/taxjar_settings.json
new file mode 100644
index 0000000..c0d60f7
--- /dev/null
+++ b/erpnext/erpnext_integrations/doctype/taxjar_settings/taxjar_settings.json
@@ -0,0 +1,110 @@
+{
+ "actions": [],
+ "creation": "2017-06-15 08:21:24.624315",
+ "doctype": "DocType",
+ "document_type": "Setup",
+ "editable_grid": 1,
+ "engine": "InnoDB",
+ "field_order": [
+  "is_sandbox",
+  "taxjar_calculate_tax",
+  "taxjar_create_transactions",
+  "credentials",
+  "api_key",
+  "cb_keys",
+  "sandbox_api_key",
+  "configuration",
+  "tax_account_head",
+  "configuration_cb",
+  "shipping_account_head"
+ ],
+ "fields": [
+  {
+   "fieldname": "credentials",
+   "fieldtype": "Section Break",
+   "label": "Credentials"
+  },
+  {
+   "fieldname": "api_key",
+   "fieldtype": "Password",
+   "in_list_view": 1,
+   "label": "Live API Key",
+   "reqd": 1
+  },
+  {
+   "fieldname": "configuration",
+   "fieldtype": "Section Break",
+   "label": "Configuration"
+  },
+  {
+   "fieldname": "tax_account_head",
+   "fieldtype": "Link",
+   "in_list_view": 1,
+   "label": "Tax Account Head",
+   "options": "Account",
+   "reqd": 1
+  },
+  {
+   "fieldname": "shipping_account_head",
+   "fieldtype": "Link",
+   "in_list_view": 1,
+   "label": "Shipping Account Head",
+   "options": "Account",
+   "reqd": 1
+  },
+  {
+   "default": "0",
+   "fieldname": "is_sandbox",
+   "fieldtype": "Check",
+   "label": "Sandbox Mode"
+  },
+  {
+   "fieldname": "sandbox_api_key",
+   "fieldtype": "Password",
+   "label": "Sandbox API Key"
+  },
+  {
+   "fieldname": "configuration_cb",
+   "fieldtype": "Column Break"
+  },
+  {
+   "default": "0",
+   "fieldname": "taxjar_create_transactions",
+   "fieldtype": "Check",
+   "label": "Create TaxJar Transaction"
+  },
+  {
+   "default": "0",
+   "fieldname": "taxjar_calculate_tax",
+   "fieldtype": "Check",
+   "label": "Enable Tax Calculation"
+  },
+  {
+   "fieldname": "cb_keys",
+   "fieldtype": "Column Break"
+  }
+ ],
+ "issingle": 1,
+ "links": [],
+ "modified": "2020-04-30 04:38:03.311089",
+ "modified_by": "Administrator",
+ "module": "ERPNext Integrations",
+ "name": "TaxJar Settings",
+ "owner": "Administrator",
+ "permissions": [
+  {
+   "create": 1,
+   "delete": 1,
+   "email": 1,
+   "print": 1,
+   "read": 1,
+   "role": "System Manager",
+   "share": 1,
+   "write": 1
+  }
+ ],
+ "quick_entry": 1,
+ "sort_field": "modified",
+ "sort_order": "DESC",
+ "track_changes": 1
+}
\ No newline at end of file
diff --git a/erpnext/erpnext_integrations/doctype/taxjar_settings/taxjar_settings.py b/erpnext/erpnext_integrations/doctype/taxjar_settings/taxjar_settings.py
new file mode 100644
index 0000000..7f5f0f0
--- /dev/null
+++ b/erpnext/erpnext_integrations/doctype/taxjar_settings/taxjar_settings.py
@@ -0,0 +1,10 @@
+# -*- coding: utf-8 -*-
+# Copyright (c) 2020, Frappe Technologies Pvt. Ltd. and contributors
+# For license information, please see license.txt
+
+from __future__ import unicode_literals
+# import frappe
+from frappe.model.document import Document
+
+class TaxJarSettings(Document):
+	pass
diff --git a/erpnext/erpnext_integrations/doctype/taxjar_settings/test_taxjar_settings.py b/erpnext/erpnext_integrations/doctype/taxjar_settings/test_taxjar_settings.py
new file mode 100644
index 0000000..7cdfd00
--- /dev/null
+++ b/erpnext/erpnext_integrations/doctype/taxjar_settings/test_taxjar_settings.py
@@ -0,0 +1,10 @@
+# -*- coding: utf-8 -*-
+# Copyright (c) 2020, Frappe Technologies Pvt. Ltd. and Contributors
+# See license.txt
+from __future__ import unicode_literals
+
+# import frappe
+import unittest
+
+class TestTaxJarSettings(unittest.TestCase):
+	pass
diff --git a/erpnext/erpnext_integrations/taxjar_integration.py b/erpnext/erpnext_integrations/taxjar_integration.py
new file mode 100644
index 0000000..633692d
--- /dev/null
+++ b/erpnext/erpnext_integrations/taxjar_integration.py
@@ -0,0 +1,251 @@
+import traceback
+
+import pycountry
+import taxjar
+
+import frappe
+from erpnext import get_default_company
+from frappe import _
+from frappe.contacts.doctype.address.address import get_company_address
+
+TAX_ACCOUNT_HEAD = frappe.db.get_single_value("TaxJar Settings", "tax_account_head")
+SHIP_ACCOUNT_HEAD = frappe.db.get_single_value("TaxJar Settings", "shipping_account_head")
+TAXJAR_CREATE_TRANSACTIONS = frappe.db.get_single_value("TaxJar Settings", "taxjar_create_transactions")
+TAXJAR_CALCULATE_TAX = frappe.db.get_single_value("TaxJar Settings", "taxjar_calculate_tax")
+SUPPORTED_COUNTRY_CODES = ["AT", "AU", "BE", "BG", "CA", "CY", "CZ", "DE", "DK", "EE", "ES", "FI",
+	"FR", "GB", "GR", "HR", "HU", "IE", "IT", "LT", "LU", "LV", "MT", "NL", "PL", "PT", "RO",
+	"SE", "SI", "SK", "US"]
+
+
+def get_client():
+	taxjar_settings = frappe.get_single("TaxJar Settings")
+
+	if not taxjar_settings.is_sandbox:
+		api_key = taxjar_settings.api_key and taxjar_settings.get_password("api_key")
+		api_url = taxjar.DEFAULT_API_URL
+	else:
+		api_key = taxjar_settings.sandbox_api_key and taxjar_settings.get_password("sandbox_api_key")
+		api_url = taxjar.SANDBOX_API_URL
+
+	if api_key and api_url:
+		return taxjar.Client(api_key=api_key, api_url=api_url)
+
+
+def create_transaction(doc, method):
+	"""Create an order transaction in TaxJar"""
+
+	if not TAXJAR_CREATE_TRANSACTIONS:
+		return
+
+	client = get_client()
+
+	if not client:
+		return
+
+	sales_tax = sum([tax.tax_amount for tax in doc.taxes if tax.account_head == TAX_ACCOUNT_HEAD])
+
+	if not sales_tax:
+		return
+
+	tax_dict = get_tax_data(doc)
+
+	if not tax_dict:
+		return
+
+	tax_dict['transaction_id'] = doc.name
+	tax_dict['transaction_date'] = frappe.utils.today()
+	tax_dict['sales_tax'] = sales_tax
+	tax_dict['amount'] = doc.total + tax_dict['shipping']
+
+	try:
+		client.create_order(tax_dict)
+	except taxjar.exceptions.TaxJarResponseError as err:
+		frappe.throw(_(sanitize_error_response(err)))
+	except Exception as ex:
+		print(traceback.format_exc(ex))
+
+
+def delete_transaction(doc, method):
+	"""Delete an existing TaxJar order transaction"""
+
+	if not TAXJAR_CREATE_TRANSACTIONS:
+		return
+
+	client = get_client()
+
+	if not client:
+		return
+
+	client.delete_order(doc.name)
+
+
+def get_tax_data(doc):
+	from_address = get_company_address_details(doc)
+	from_shipping_state = from_address.get("state")
+	from_country_code = frappe.db.get_value("Country", from_address.country, "code")
+	from_country_code = from_country_code.upper()
+
+	to_address = get_shipping_address_details(doc)
+	to_shipping_state = to_address.get("state")
+	to_country_code = frappe.db.get_value("Country", to_address.country, "code")
+	to_country_code = to_country_code.upper()
+
+	if to_country_code not in SUPPORTED_COUNTRY_CODES:
+		return
+
+	shipping = sum([tax.tax_amount for tax in doc.taxes if tax.account_head == SHIP_ACCOUNT_HEAD])
+
+	if to_shipping_state is not None:
+		to_shipping_state = get_iso_3166_2_state_code(to_address)
+
+	tax_dict = {
+		'from_country': from_country_code,
+		'from_zip': from_address.pincode,
+		'from_state': from_shipping_state,
+		'from_city': from_address.city,
+		'from_street': from_address.address_line1,
+		'to_country': to_country_code,
+		'to_zip': to_address.pincode,
+		'to_city': to_address.city,
+		'to_street': to_address.address_line1,
+		'to_state': to_shipping_state,
+		'shipping': shipping,
+		'amount': doc.net_total
+	}
+
+	return tax_dict
+
+
+def set_sales_tax(doc, method):
+	if not TAXJAR_CALCULATE_TAX:
+		return
+
+	if not doc.items:
+		return
+
+	# if the party is exempt from sales tax, then set all tax account heads to zero
+	sales_tax_exempted = hasattr(doc, "exempt_from_sales_tax") and doc.exempt_from_sales_tax \
+		or frappe.db.has_column("Customer", "exempt_from_sales_tax") and frappe.db.get_value("Customer", doc.customer, "exempt_from_sales_tax")
+
+	if sales_tax_exempted:
+		for tax in doc.taxes:
+			if tax.account_head == TAX_ACCOUNT_HEAD:
+				tax.tax_amount = 0
+				break
+
+		doc.run_method("calculate_taxes_and_totals")
+		return
+
+	tax_dict = get_tax_data(doc)
+
+	if not tax_dict:
+		# Remove existing tax rows if address is changed from a taxable state/country
+		setattr(doc, "taxes", [tax for tax in doc.taxes if tax.account_head != TAX_ACCOUNT_HEAD])
+		return
+
+	tax_data = validate_tax_request(tax_dict)
+
+	if tax_data is not None:
+		if not tax_data.amount_to_collect:
+			setattr(doc, "taxes", [tax for tax in doc.taxes if tax.account_head != TAX_ACCOUNT_HEAD])
+		elif tax_data.amount_to_collect > 0:
+			# Loop through tax rows for existing Sales Tax entry
+			# If none are found, add a row with the tax amount
+			for tax in doc.taxes:
+				if tax.account_head == TAX_ACCOUNT_HEAD:
+					tax.tax_amount = tax_data.amount_to_collect
+
+					doc.run_method("calculate_taxes_and_totals")
+					break
+			else:
+				doc.append("taxes", {
+					"charge_type": "Actual",
+					"description": "Sales Tax",
+					"account_head": TAX_ACCOUNT_HEAD,
+					"tax_amount": tax_data.amount_to_collect
+				})
+
+			doc.run_method("calculate_taxes_and_totals")
+
+
+def validate_tax_request(tax_dict):
+	"""Return the sales tax that should be collected for a given order."""
+
+	client = get_client()
+
+	if not client:
+		return
+
+	try:
+		tax_data = client.tax_for_order(tax_dict)
+	except taxjar.exceptions.TaxJarResponseError as err:
+		frappe.throw(_(sanitize_error_response(err)))
+	else:
+		return tax_data
+
+
+def get_company_address_details(doc):
+	"""Return default company address details"""
+
+	company_address = get_company_address(get_default_company()).company_address
+
+	if not company_address:
+		frappe.throw(_("Please set a default company address"))
+
+	company_address = frappe.get_doc("Address", company_address)
+	return company_address
+
+
+def get_shipping_address_details(doc):
+	"""Return customer shipping address details"""
+
+	if doc.shipping_address_name:
+		shipping_address = frappe.get_doc("Address", doc.shipping_address_name)
+	else:
+		shipping_address = get_company_address_details(doc)
+
+	return shipping_address
+
+
+def get_iso_3166_2_state_code(address):
+	country_code = frappe.db.get_value("Country", address.get("country"), "code")
+
+	error_message = _("""{0} is not a valid state! Check for typos or enter the ISO code for your state.""").format(address.get("state"))
+	state = address.get("state").upper().strip()
+
+	# The max length for ISO state codes is 3, excluding the country code
+	if len(state) <= 3:
+		# PyCountry returns state code as {country_code}-{state-code} (e.g. US-FL)
+		address_state = (country_code + "-" + state).upper()
+
+		states = pycountry.subdivisions.get(country_code=country_code.upper())
+		states = [pystate.code for pystate in states]
+
+		if address_state in states:
+			return state
+
+		frappe.throw(_(error_message))
+	else:
+		try:
+			lookup_state = pycountry.subdivisions.lookup(state)
+		except LookupError:
+			frappe.throw(_(error_message))
+		else:
+			return lookup_state.code.split('-')[1]
+
+
+def sanitize_error_response(response):
+	response = response.full_response.get("detail")
+	response = response.replace("_", " ")
+
+	sanitized_responses = {
+		"to zip": "Zipcode",
+		"to city": "City",
+		"to state": "State",
+		"to country": "Country"
+	}
+
+	for k, v in sanitized_responses.items():
+		response = response.replace(k, v)
+
+	return response
diff --git a/erpnext/hooks.py b/erpnext/hooks.py
index 2a69589..835d92e 100644
--- a/erpnext/hooks.py
+++ b/erpnext/hooks.py
@@ -234,8 +234,15 @@
 		"validate": "erpnext.portal.doctype.products_settings.products_settings.home_page_is_products"
 	},
 	"Sales Invoice": {
-		"on_submit": ["erpnext.regional.create_transaction_log", "erpnext.regional.italy.utils.sales_invoice_on_submit"],
-		"on_cancel": "erpnext.regional.italy.utils.sales_invoice_on_cancel",
+		"on_submit": [
+			"erpnext.regional.create_transaction_log",
+			"erpnext.regional.italy.utils.sales_invoice_on_submit",
+			"erpnext.erpnext_integrations.taxjar_integration.create_transaction"
+		],
+		"on_cancel": [
+			"erpnext.regional.italy.utils.sales_invoice_on_cancel",
+			"erpnext.erpnext_integrations.taxjar_integration.delete_transaction"
+		],
 		"on_trash": "erpnext.regional.check_deletion_permission"
 	},
 	"Purchase Invoice": {
@@ -261,6 +268,9 @@
 	},
 	"Email Unsubscribe": {
 		"after_insert": "erpnext.crm.doctype.email_campaign.email_campaign.unsubscribe_recipient"
+	},
+	('Quotation', 'Sales Order', 'Sales Invoice'): {
+		'validate': ["erpnext.erpnext_integrations.taxjar_integration.set_sales_tax"]
 	}
 }
 
diff --git a/erpnext/patches.txt b/erpnext/patches.txt
index 17fbcc2..c7a7abf 100644
--- a/erpnext/patches.txt
+++ b/erpnext/patches.txt
@@ -706,3 +706,4 @@
 erpnext.patches.v13_0.move_doctype_reports_and_notification_from_hr_to_payroll #22-06-2020
 erpnext.patches.v13_0.move_payroll_setting_separately_from_hr_settings #22-06-2020
 erpnext.patches.v13_0.check_is_income_tax_component #22-06-2020
+erpnext.patches.v12_0.add_taxjar_integration_field
diff --git a/erpnext/patches/v12_0/add_taxjar_integration_field.py b/erpnext/patches/v12_0/add_taxjar_integration_field.py
new file mode 100644
index 0000000..4c823e1
--- /dev/null
+++ b/erpnext/patches/v12_0/add_taxjar_integration_field.py
@@ -0,0 +1,12 @@
+from __future__ import unicode_literals
+
+import frappe
+from erpnext.regional.united_states.setup import make_custom_fields
+
+
+def execute():
+	company = frappe.get_all('Company', filters={'country': 'United States'})
+	if not company:
+		return
+
+	make_custom_fields()
diff --git a/erpnext/regional/united_states/setup.py b/erpnext/regional/united_states/setup.py
index cae28be..2b0ecaf 100644
--- a/erpnext/regional/united_states/setup.py
+++ b/erpnext/regional/united_states/setup.py
@@ -14,6 +14,22 @@
 		'Supplier': [
 			dict(fieldname='irs_1099', fieldtype='Check', insert_after='tax_id',
 				label='Is IRS 1099 reporting required for supplier?')
+		],
+		'Sales Order': [
+			dict(fieldname='exempt_from_sales_tax', fieldtype='Check', insert_after='taxes_and_charges',
+				label='Is customer exempted from sales tax?')
+		],
+		'Sales Invoice': [
+			dict(fieldname='exempt_from_sales_tax', fieldtype='Check', insert_after='taxes_section',
+				label='Is customer exempted from sales tax?')
+		],
+		'Customer': [
+			dict(fieldname='exempt_from_sales_tax', fieldtype='Check', insert_after='represents_company',
+				label='Is customer exempted from sales tax?')
+		],
+		'Quotation': [
+			dict(fieldname='exempt_from_sales_tax', fieldtype='Check', insert_after='taxes_and_charges',
+				label='Is customer exempted from sales tax?')
 		]
 	}
 	create_custom_fields(custom_fields, update=update)
diff --git a/erpnext/selling/doctype/quotation/test_quotation.py b/erpnext/selling/doctype/quotation/test_quotation.py
index ee6b429..b4c3d79 100644
--- a/erpnext/selling/doctype/quotation/test_quotation.py
+++ b/erpnext/selling/doctype/quotation/test_quotation.py
@@ -280,5 +280,3 @@
 			qo.submit()
 
 	return qo
-
-
diff --git a/requirements.txt b/requirements.txt
index 9da537e..cfd0ab8 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -4,8 +4,10 @@
 googlemaps==3.1.1
 pandas==0.24.2
 plaid-python==3.4.0
+pycountry==19.8.18
 PyGithub==1.44.1
 python-stdnum==1.12
+taxjar==1.9.0
+tweepy==3.8.0
 Unidecode==1.1.1
 WooCommerce==2.1.1
-tweepy==3.8.0
\ No newline at end of file