diff --git a/command/acl.go b/command/acl.go
index 3a6461a22..4cc45a18c 100644
--- a/command/acl.go
+++ b/command/acl.go
@@ -12,11 +12,17 @@ type ACLCommand struct {
 
 func (f *ACLCommand) Help() string {
 	helpText := `
-Usage: nomad acl <subcommand> [options]
+Usage: nomad acl <subcommand> [options] [args]
 
-  Interact with ACL policies and tokens.
+  This command groups subcommands for interacting with ACL policies and tokens.
+  Users can bootstrap Nomad's ACL system, create policies that restrict access,
+  and generate tokens from those policies.
 
-  Run nomad acl <subcommand> with no arguments for help on that subcommand.
+  Bootstrap ACLs:
+
+      $ nomad acl bootstrap
+
+  Please see the individual subcommand help for detailed usage information.
 `
 	return strings.TrimSpace(helpText)
 }
diff --git a/command/acl_policy.go b/command/acl_policy.go
index 43eaf26dc..28e9e1be0 100644
--- a/command/acl_policy.go
+++ b/command/acl_policy.go
@@ -1,13 +1,39 @@
 package command
 
-import "github.com/mitchellh/cli"
+import (
+	"strings"
+
+	"github.com/mitchellh/cli"
+)
 
 type ACLPolicyCommand struct {
 	Meta
 }
 
 func (f *ACLPolicyCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad acl policy <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with ACL policies. Nomad's ACL
+  system can be used to control access to data and APIs. ACL policies allow a
+  set of capabilities or actions to be granted or whitelisted. For a full guide
+  see: https://www.nomadproject.io/guides/acl.html
+
+  Create an ACL policy:
+
+      $ nomad acl policy apply <name> <policy-file>
+
+  List ACL policies:
+
+      $ nomad acl policy list
+
+  Inspect an ACL policy:
+
+      $ nomad acl policy info <policy>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+	return strings.TrimSpace(helpText)
 }
 
 func (f *ACLPolicyCommand) Synopsis() string {
diff --git a/command/acl_token.go b/command/acl_token.go
index d11f06b6a..8f1faa503 100644
--- a/command/acl_token.go
+++ b/command/acl_token.go
@@ -1,13 +1,39 @@
 package command
 
-import "github.com/mitchellh/cli"
+import (
+	"strings"
+
+	"github.com/mitchellh/cli"
+)
 
 type ACLTokenCommand struct {
 	Meta
 }
 
 func (f *ACLTokenCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad acl token <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with ACL tokens. Nomad's ACL
+  system can be used to control access to data and APIs. ACL tokens are
+  associated with one or more ACL policies which grant specific capabilities.
+  For a full guide see: https://www.nomadproject.io/guides/acl.html
+
+  Create an ACL token:
+
+      $ nomad acl token create -name "my-token" -policy foo -policy bar
+
+  Lookup a token and display its associated policies:
+
+      $ nomad acl policy info <token_accessor_id>
+
+  Revoke an ACL token:
+
+      $ nomad acl policy delete <token_accessor_id>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+	return strings.TrimSpace(helpText)
 }
 
 func (f *ACLTokenCommand) Synopsis() string {
diff --git a/command/alloc.go b/command/alloc.go
index f2729a42f..04f232b3f 100644
--- a/command/alloc.go
+++ b/command/alloc.go
@@ -1,13 +1,34 @@
 package command
 
-import "github.com/mitchellh/cli"
+import (
+	"strings"
+
+	"github.com/mitchellh/cli"
+)
 
 type AllocCommand struct {
 	Meta
 }
 
 func (f *AllocCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad alloc <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with allocations. Users can
+  inspect the status, examine the filesystem or logs of an allocation.
+
+  Examine an allocations status:
+
+      $ nomad alloc status <alloc-id>
+
+  Stream a task's logs:
+
+      $ nomad alloc logs -f <alloc-id> <task>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+
+	return strings.TrimSpace(helpText)
 }
 
 func (f *AllocCommand) Synopsis() string {
diff --git a/command/deployment.go b/command/deployment.go
index 8c4328a53..d30bfa4a3 100644
--- a/command/deployment.go
+++ b/command/deployment.go
@@ -1,13 +1,43 @@
 package command
 
-import "github.com/mitchellh/cli"
+import (
+	"strings"
+
+	"github.com/mitchellh/cli"
+)
 
 type DeploymentCommand struct {
 	Meta
 }
 
 func (f *DeploymentCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad deployment <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with deployments. Deployments
+  are used to manage a transistion between two versions of a Nomad job. Users
+  can inspect an ongoing deployment, promote canary allocations, force fail
+  deployments, and more.
+
+  Examine a deployments status:
+
+      $ nomad deployment status <deployment-id>
+
+  Promote the canaries to allow the remaining allocations to be updated in a
+  rolling deployment fashion:
+
+      $ nomad deployment promote <depoloyment-id>
+
+  Mark a deployment as failed. This will stop new allocations from being placed
+  and if the job's upgrade stanza specifies auto_revert, causes the job to
+  revert back to the last stable version of the job:
+
+      $ nomad deployment fail <depoloyment-id>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+
+	return strings.TrimSpace(helpText)
 }
 
 func (f *DeploymentCommand) Synopsis() string {
diff --git a/command/eval.go b/command/eval.go
index 70959d181..a1031634f 100644
--- a/command/eval.go
+++ b/command/eval.go
@@ -1,13 +1,32 @@
 package command
 
-import "github.com/mitchellh/cli"
+import (
+	"strings"
+
+	"github.com/mitchellh/cli"
+)
 
 type EvalCommand struct {
 	Meta
 }
 
 func (f *EvalCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad eval <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with evaluations. Evaluations
+  are used to trigger a scheduling event. As such, evaluations are an internal
+  detail but can be useful for debugging placement failures when the cluster
+  does not have the resources to run a given job.
+
+  Examine an evaluations status:
+
+      $ nomad eval status <eval-id>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+
+	return strings.TrimSpace(helpText)
 }
 
 func (f *EvalCommand) Synopsis() string {
diff --git a/command/job.go b/command/job.go
index 35477146f..36d0e1ce2 100644
--- a/command/job.go
+++ b/command/job.go
@@ -1,13 +1,41 @@
 package command
 
-import "github.com/mitchellh/cli"
+import (
+	"strings"
+
+	"github.com/mitchellh/cli"
+)
 
 type JobCommand struct {
 	Meta
 }
 
 func (f *JobCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad job <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with jobs.
+
+  Run a new job or update an existing job:
+
+      $ nomad job run <path>
+
+  Plan the run of a job to determine what changes would occur:
+
+      $ nomad job plan <path>
+
+  Stop a running job:
+
+      $ nomad job stop <name>
+
+  Examine the status of a running job:
+
+      $ nomad job status <name>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+
+	return strings.TrimSpace(helpText)
 }
 
 func (f *JobCommand) Synopsis() string {
diff --git a/command/namespace.go b/command/namespace.go
index 5533614a4..d43deec84 100644
--- a/command/namespace.go
+++ b/command/namespace.go
@@ -1,6 +1,8 @@
 package command
 
 import (
+	"strings"
+
 	"github.com/hashicorp/nomad/api/contexts"
 	"github.com/mitchellh/cli"
 	"github.com/posener/complete"
@@ -11,7 +13,30 @@ type NamespaceCommand struct {
 }
 
 func (f *NamespaceCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad namespace <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with namespaces. Namespaces
+  allow jobs and their associated objects to be segmented from each other and
+  other users of the cluster. For a full guide on namespaces see:
+  https://www.nomadproject.io/guides/namespaces.html
+
+  Create or update a namespace:
+
+      $ nomad namespace apply <name> -description "My new namespace"
+
+  List namespaces:
+
+      $ nomad namespace list
+
+  View the status of a namespace:
+
+      $ nomad namespace status <name>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+
+	return strings.TrimSpace(helpText)
 }
 
 func (f *NamespaceCommand) Synopsis() string {
diff --git a/command/node.go b/command/node.go
index 36436d9b7..0479d0b20 100644
--- a/command/node.go
+++ b/command/node.go
@@ -1,13 +1,41 @@
 package command
 
-import "github.com/mitchellh/cli"
+import (
+	"strings"
+
+	"github.com/mitchellh/cli"
+)
 
 type NodeCommand struct {
 	Meta
 }
 
 func (f *NodeCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad nomad <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with nodes. Nodes in Nomad are
+  agent's that can run submitted workloads. This command can be used to examine
+  nodes and operate on nodes, such as draining workloads off of them.
+
+  Examine the status of a node:
+
+      $ nomad node status <node-id>
+
+  Mark a node as ineligible for running workloads. This is useful when the node
+  is expected to be removed or upgraded so new allocations aren't placed on it:
+
+      $ nomad node eligibility -disabled <node-id>
+
+  Mark a node to be drained, allowing batch jobs four hours to finished before
+  forcing them off the node:
+
+      $ nomad node drain -enable -deadline 4h <node-id>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+
+	return strings.TrimSpace(helpText)
 }
 
 func (f *NodeCommand) Synopsis() string {
diff --git a/command/operator.go b/command/operator.go
index db5ed3574..850154ba6 100644
--- a/command/operator.go
+++ b/command/operator.go
@@ -18,7 +18,7 @@ Usage: nomad operator <subcommand> [options]
   the Raft subsystem. NOTE: Use this command with extreme caution, as improper
   use could lead to a Nomad outage and even loss of data.
 
-  Run nomad operator <subcommand> with no arguments for help on that subcommand.
+  Please see the individual subcommand help for detailed usage information.
 `
 	return strings.TrimSpace(helpText)
 }
diff --git a/command/operator_autopilot.go b/command/operator_autopilot.go
index d4c4cdd5b..49fef0bc4 100644
--- a/command/operator_autopilot.go
+++ b/command/operator_autopilot.go
@@ -22,8 +22,49 @@ func (c *OperatorAutopilotCommand) Help() string {
 	helpText := `
 Usage: nomad operator autopilot <subcommand> [options]
 
-  The Autopilot operator command is used to interact with Nomad's Autopilot
-  subsystem. The command can be used to view or modify the current configuration.
-`
+  This command groups subcommands for interacting with Nomad's Autopilot
+  subsystem. Autopilot provides automatic, operator-friendly management of Nomad
+  servers. The command can be used to view or modify the current Autopilot
+  configuration.
+
+  Get the current Autopilot configuration:
+
+      $ nomad operator autopilot get-config
+  
+  Set a new Autopilot configuration, enabling automatic dead server cleanup:
+
+      $ nomad operator autopilot set-config -cleanup-dead-servers=true
+  
+  Please see the individual subcommand help for detailed usage information.
+  `
 	return strings.TrimSpace(helpText)
+	/*
+			helpText := `
+		Usage: nomad deployment <subcommand> [options] [args]
+
+		  This command groups subcommands for interacting with deployments. Deployments
+		  are used to manage a transistion between two versions of a Nomad job. Users
+		  can inspect an ongoing deployment, promote canary allocations, force fail
+		  deployments, and more.
+
+		  Examine a deployments status:
+
+		      $ nomad deployment status <deployment-id>
+
+		  Promote the canaries to allow the remaining allocations to be updated in a
+		  rolling deployment fashion:
+
+		      $ nomad deployment promote <depoloyment-id>
+
+		  Mark a deployment as failed. This will stop new allocations from being placed
+		  and if the job's upgrade stanza specifies auto_revert, causes the job to
+		  revert back to the last stable version of the job:
+
+		      $ nomad deployment fail <depoloyment-id>
+
+		  Please see the individual subcommand help for detailed usage information.
+		`
+
+			return strings.TrimSpace(helpText)
+	*/
 }
diff --git a/command/operator_raft.go b/command/operator_raft.go
index 16d89e77f..5d6df4ead 100644
--- a/command/operator_raft.go
+++ b/command/operator_raft.go
@@ -14,9 +14,19 @@ func (c *OperatorRaftCommand) Help() string {
 	helpText := `
 Usage: nomad operator raft <subcommand> [options]
 
-  The Raft operator command is used to interact with Nomad's Raft subsystem. The
-  command can be used to verify Raft peers or in rare cases to recover quorum by
-  removing invalid peers.
+  This command groups subcommands for interacting with Nomad's Raft subsystem.
+  The command can be used to verify Raft peers or in rare cases to recover
+  quorum by removing invalid peers.
+
+  List Raft peers:
+
+      $ nomad operator raft list-peers
+
+  Remove a Raft peer:
+
+      $ nomad operator raft remove-peer -peer-address "IP:Port"
+
+  Please see the individual subcommand help for detailed usage information.
 `
 	return strings.TrimSpace(helpText)
 }
diff --git a/command/quota.go b/command/quota.go
index 46959d5a4..62d357081 100644
--- a/command/quota.go
+++ b/command/quota.go
@@ -1,6 +1,8 @@
 package command
 
 import (
+	"strings"
+
 	"github.com/hashicorp/nomad/api/contexts"
 	"github.com/mitchellh/cli"
 	"github.com/posener/complete"
@@ -11,7 +13,31 @@ type QuotaCommand struct {
 }
 
 func (f *QuotaCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad quota <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with resource quotas. Resource
+  quotas allow operators to restrict the aggregate resource usage of namespaces.
+  Users can inspect existing quota specifications, create new quotas, delete and
+  list existing quotas, and more. For a full guide on resource quotas see:
+  https://www.nomadproject.io/guides/quotas.html 
+
+  Examine a quota's status:
+
+      $ nomad quota status <name>
+
+  List existing quotas:
+
+      $ nomad quota list
+
+  Create a new quota specification:
+
+      $ nomad quota apply <path>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+
+	return strings.TrimSpace(helpText)
 }
 
 func (f *QuotaCommand) Synopsis() string {
diff --git a/command/sentinel.go b/command/sentinel.go
index fe8ffba60..4e30f98bf 100644
--- a/command/sentinel.go
+++ b/command/sentinel.go
@@ -1,13 +1,44 @@
 package command
 
-import "github.com/mitchellh/cli"
+import (
+	"strings"
+
+	"github.com/mitchellh/cli"
+)
 
 type SentinelCommand struct {
 	Meta
 }
 
 func (f *SentinelCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad sentinel <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with Sentinel policies.
+  Sentinel policies allow operators to express fine-grained policies as code and
+  have their policies automatically enforced. This allows operators to define a
+  "sandbox" and restrict actions to only those compliant with policy. The
+  Sentinel integration builds on the ACL System. Users can read existing
+  Sentinel policies, create new policies, delete and list existing policies, and
+  more. For a full guide on Sentinel policies see:
+  https://www.nomadproject.io/guides/sentinel-policy.html
+
+  Read an existing policy:
+
+      $ nomad sentinel read <name>
+
+  List existing policies:
+
+      $ nomad sentinel list
+
+  Create a new Sentinel policy:
+
+      $ nomad sentinel apply <name> <path>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+
+	return strings.TrimSpace(helpText)
 }
 
 func (f *SentinelCommand) Synopsis() string {
diff --git a/command/server.go b/command/server.go
index 7735fcc87..f675869cb 100644
--- a/command/server.go
+++ b/command/server.go
@@ -1,13 +1,38 @@
 package command
 
-import "github.com/mitchellh/cli"
+import (
+	"strings"
+
+	"github.com/mitchellh/cli"
+)
 
 type ServerCommand struct {
 	Meta
 }
 
 func (f *ServerCommand) Help() string {
-	return "This command is accessed by using one of the subcommands below."
+	helpText := `
+Usage: nomad server <subcommand> [options] [args]
+
+  This command groups subcommands for interacting with Nomad servers. Users can
+  list Servers, join a server to the cluster, and force leave a server.
+
+  List Nomad servers:
+
+      $ nomad server members
+
+  Join a new server to another:
+
+      $ nomad server join "IP:Port"
+
+  Force a server to leave:
+
+      $ nomad server force-leave <name>
+
+  Please see the individual subcommand help for detailed usage information.
+`
+
+	return strings.TrimSpace(helpText)
 }
 
 func (f *ServerCommand) Synopsis() string {