diff --git a/nucypher/cli/commands/deploy.py b/nucypher/cli/commands/deploy.py
index 7dbc36e0b..cc0c26fe7 100644
--- a/nucypher/cli/commands/deploy.py
+++ b/nucypher/cli/commands/deploy.py
@@ -50,6 +50,7 @@ from nucypher.cli.literature import (
     CONFIRM_NETWORK_ACTIVATION,
     CONFIRM_RETARGET,
     CONFIRM_SELECTED_ACCOUNT,
+    CONFIRM_TOKEN_ALLOWANCE,
     CONFIRM_TOKEN_TRANSFER,
     CONTRACT_DEPLOYMENT_SERIES_BEGIN_ADVISORY,
     CONTRACT_IS_NOT_OWNABLE,
@@ -529,7 +530,8 @@ def allocations(general_config, actor_options, allocation_infile, gas):
 @group_actor_options
 @option_target_address
 @click.option('--value', help="Amount of tokens to transfer in the smallest denomination", type=click.INT)
-def transfer_tokens(general_config, actor_options, target_address, value):
+@click.option('--approve', help="Approve token allowance, instead of transfer", is_flag=True, default=False)
+def transfer_tokens(general_config, actor_options, target_address, value, approve):
     """Transfer tokens from contract's owner address to another address"""
 
     emitter = general_config.emitter
@@ -544,13 +546,23 @@ def transfer_tokens(general_config, actor_options, target_address, value):
         stake_value_range = click.FloatRange(min=0, clamp=False)
         value = NU.from_tokens(click.prompt(PROMPT_TOKEN_VALUE, type=stake_value_range))
 
-    confirmation = CONFIRM_TOKEN_TRANSFER.format(value=value,
-                                                 deployer_address=deployer_address,
-                                                 target_address=target_address)
+    value = NuNits(int(value))
+    if approve:
+        confirmation = CONFIRM_TOKEN_ALLOWANCE.format(value=value,
+                                                      deployer_address=deployer_address,
+                                                      spender_address=target_address)
+    else:
+        confirmation = CONFIRM_TOKEN_TRANSFER.format(value=value,
+                                                     deployer_address=deployer_address,
+                                                     target_address=target_address)
     click.confirm(confirmation, abort=True)
-    receipt = token_agent.transfer(amount=NuNits(int(value)),
-                                   sender_address=deployer_address,
-                                   target_address=target_address)
+
+    if approve:
+        receipt = token_agent.approve_transfer(amount=value,
+                                               sender_address=deployer_address,
+                                               spender_address=target_address)
+    else:
+        receipt = token_agent.transfer(amount=value, sender_address=deployer_address, target_address=target_address)
     paint_receipt_summary(emitter=emitter, receipt=receipt)
 
 
diff --git a/nucypher/cli/literature.py b/nucypher/cli/literature.py
index 445b30c7a..b31300aab 100644
--- a/nucypher/cli/literature.py
+++ b/nucypher/cli/literature.py
@@ -358,6 +358,8 @@ The staker's fee rate was set to the default value {default} such that it falls
 
 CONTRACT_IS_NOT_OWNABLE = "Contract {contract_name} is not ownable."
 
+CONFIRM_TOKEN_ALLOWANCE = "Approve allowance of {value} from {deployer_address} to {spender_address}?"
+
 CONFIRM_TOKEN_TRANSFER = "Transfer {value} from {deployer_address} to {target_address}?"
 
 PROMPT_TOKEN_VALUE = "Enter value in NU"
diff --git a/tests/acceptance/cli/test_deploy.py b/tests/acceptance/cli/test_deploy.py
index 9cb1a1e1d..47c0ca98d 100644
--- a/tests/acceptance/cli/test_deploy.py
+++ b/tests/acceptance/cli/test_deploy.py
@@ -128,13 +128,10 @@ def test_deploy_single_contract(click_runner, tempfile_path):
     assert result.exit_code == 0
 
 
-def test_transfer_tokens(click_runner, registry_filepath):
-    #
-    # Setup
-    #
+def test_transfer_tokens(click_runner, registry_filepath, get_random_checksum_address, testerchain):
 
     # Let's transfer some NU to a random stranger
-    recipient_address = to_checksum_address(os.urandom(20))
+    recipient_address = get_random_checksum_address()
 
     registry = LocalContractRegistry(filepath=registry_filepath)
     token_agent = NucypherTokenAgent(registry=registry)
@@ -153,6 +150,25 @@ def test_transfer_tokens(click_runner, registry_filepath):
     # Check that the NU has arrived to the recipient
     assert token_agent.get_balance(address=recipient_address) == 42
 
+    # Let's approve an allowance to a random spender
+    spender_address = get_random_checksum_address()
+    owner_address = testerchain.client.accounts[0]
+    assert token_agent.get_allowance(spender=spender_address, owner=owner_address) == 0
+
+    command = ['transfer-tokens',
+               '--target-address', spender_address,
+               '--value', 42,
+               '--approve',
+               '--registry-infile', registry_filepath,
+               '--provider', TEST_PROVIDER_URI]
+
+    user_input = '0\n' + 'Y\n' + 'Y\n'
+    result = click_runner.invoke(deploy, command, input=user_input, catch_exceptions=False)
+    assert result.exit_code == 0
+
+    # Check that the NU was approved for the spender
+    assert token_agent.get_allowance(spender=spender_address, owner=owner_address) == 42
+
 
 def test_upgrade_contracts(click_runner, registry_filepath, testerchain):