diff --git a/app/models/http_endpoint.rb b/app/models/http_endpoint.rb
index 8cd9044..393b785 100644
--- a/app/models/http_endpoint.rb
+++ b/app/models/http_endpoint.rb
@@ -1,5 +1,7 @@
 # frozen_string_literal: true
 
+require "uri"
+
 # == Schema Information
 #
 # Table name: http_endpoints
@@ -38,6 +40,7 @@ class HTTPEndpoint < ApplicationRecord
 
   validates :name, presence: true
   validates :url, presence: true
+  validate :url_must_be_http_or_https
   validates :encoding, inclusion: { in: ENCODINGS }
   validates :format, inclusion: { in: FORMATS }
   validates :timeout, numericality: { greater_than_or_equal_to: 5, less_than_or_equal_to: 60 }
@@ -56,4 +59,17 @@ class HTTPEndpoint < ApplicationRecord
     routes.each { |r| r.update(endpoint: nil, mode: "Reject") }
   end
 
+  private
+
+  def url_must_be_http_or_https
+    return if url.blank?
+
+    uri = URI.parse(url)
+    return if uri.is_a?(URI::HTTP) && uri.host.present?
+
+    errors.add(:url, "must be an HTTP or HTTPS URL")
+  rescue URI::InvalidURIError
+    errors.add(:url, "must be a valid HTTP or HTTPS URL")
+  end
+
 end
diff --git a/lib/postal/config_schema.rb b/lib/postal/config_schema.rb
index e3c6415..871d094 100644
--- a/lib/postal/config_schema.rb
+++ b/lib/postal/config_schema.rb
@@ -92,6 +92,14 @@ module Postal
         transform { |ip| IPAddr.new(ip) }
       end
 
+      string :allowed_request_destinations do
+        array
+        description "Hostnames or IP/CIDR ranges that outbound webhook and HTTP " \
+                    "endpoint requests are permitted to reach even when they resolve " \
+                    "to a private, loopback, link-local or otherwise reserved address. " \
+                    "All other such destinations are blocked to prevent SSRF."
+      end
+
       integer :queued_message_lock_stale_days do
         description "The number of days after which to consider a lock as stale. Messages with stale locks will be removed and not retried."
         default 1
diff --git a/lib/postal/http.rb b/lib/postal/http.rb
index 8a32d9b..4f17feb 100644
--- a/lib/postal/http.rb
+++ b/lib/postal/http.rb
@@ -1,6 +1,7 @@
 # frozen_string_literal: true
 
 require "net/https"
+require "resolv"
 require "uri"
 
 module Postal
@@ -47,19 +48,24 @@ module Postal
 
       request["User-Agent"] = options[:user_agent] || "Postal/#{Postal.version}"
 
-      connection = Net::HTTP.new(uri.host, uri.port)
-
-      if uri.scheme == "https"
-        connection.use_ssl = true
-        connection.verify_mode = OpenSSL::SSL::VERIFY_PEER
-        ssl = true
-      else
-        ssl = false
-      end
+      timeout = options[:timeout] || 60
+      ssl = uri.scheme == "https"
 
       begin
-        timeout = options[:timeout] || 60
         Timeout.timeout(timeout) do
+          connect_address = AddressGuard.safe_connect_address(uri.host)
+
+          connection = Net::HTTP.new(uri.host, uri.port)
+          # Pin the connection to the address we validated above so that the socket
+          # cannot be redirected to a different (e.g. internal) address via a DNS
+          # rebinding race between the check and the connection.
+          connection.ipaddr = connect_address
+
+          if uri.scheme == "https"
+            connection.use_ssl = true
+            connection.verify_mode = OpenSSL::SSL::VERIFY_PEER
+          end
+
           result = connection.request(request)
           {
             code: result.code.to_i,
@@ -68,6 +74,13 @@ module Postal
             secure: ssl
           }
         end
+      rescue BlockedDestinationError => e
+        {
+          code: -4,
+          body: e.message,
+          headers: {},
+          secure: ssl
+        }
       rescue OpenSSL::SSL::SSLError
         {
           code: -3,
@@ -75,7 +88,7 @@ module Postal
           headers: {},
           secure: ssl
         }
-      rescue SocketError, Errno::ECONNRESET, EOFError, Errno::EINVAL, Errno::ENETUNREACH, Errno::EHOSTUNREACH, Errno::ECONNREFUSED => e
+      rescue Resolv::ResolvError, SocketError, SystemCallError, EOFError => e
         {
           code: -2,
           body: e.message,
diff --git a/lib/postal/http/address_guard.rb b/lib/postal/http/address_guard.rb
new file mode 100644
index 0000000..ed863d2
--- /dev/null
+++ b/lib/postal/http/address_guard.rb
@@ -0,0 +1,202 @@
+# frozen_string_literal: true
+
+require "ipaddr"
+require "resolv"
+require "socket"
+
+module Postal
+  module HTTP
+    # Guards outbound HTTP requests against SSRF by resolving the destination
+    # host and refusing to connect to private, loopback, link-local, multicast
+    # or otherwise reserved addresses (for example cloud metadata endpoints).
+    #
+    # Administrators can permit specific destinations by adding hostnames or
+    # IP/CIDR ranges to the `postal.allowed_request_destinations` config option.
+    class AddressGuard
+
+      # IP ranges that outbound requests are never allowed to reach unless the
+      # destination has been explicitly allowlisted.
+      BLOCKED_RANGES = [
+        # IPv4
+        "0.0.0.0/8",        # "this host on this network"
+        "10.0.0.0/8",       # RFC1918 private
+        "100.64.0.0/10",    # RFC6598 carrier-grade NAT
+        "127.0.0.0/8",      # loopback
+        "169.254.0.0/16",   # link-local (incl. 169.254.169.254 metadata)
+        "172.16.0.0/12",    # RFC1918 private
+        "192.0.0.0/24",     # IETF protocol assignments
+        "192.168.0.0/16",   # RFC1918 private
+        "198.18.0.0/15",    # benchmarking
+        "224.0.0.0/4",      # multicast
+        "240.0.0.0/4",      # reserved
+        # IPv6
+        "::/128",           # unspecified
+        "::1/128",          # loopback
+        "::ffff:0:0/96",    # IPv4-mapped (also re-checked against the v4 list)
+        "fc00::/7",         # unique-local
+        "fe80::/10",        # link-local
+        "ff00::/8", # multicast
+      ].map { |range| IPAddr.new(range) }.freeze
+
+      class << self
+
+        # Resolve and validate the given host, returning the IP address the
+        # connection should be pinned to (as a string). Pinning the connection
+        # to the validated address prevents a DNS-rebinding race between the
+        # check here and the actual connection.
+        #
+        # @param [String] host the hostname or IP literal from the request URL
+        # @raise [Postal::HTTP::BlockedDestinationError] if the host cannot be
+        #   resolved or any resolved address is not permitted
+        # @raise [SocketError] if the host only resolves to addresses whose
+        #   family this server cannot reach (e.g. IPv6 with no IPv6 support)
+        # @return [String] the validated IP address to connect to
+        def safe_connect_address(host)
+          new(host).safe_connect_address
+        end
+
+        # Whether this server has IPv6 connectivity (a global IPv6 address on
+        # one of its interfaces). Memoized as it does not change at runtime.
+        def ipv6_supported?
+          return @ipv6_supported unless @ipv6_supported.nil?
+
+          @ipv6_supported = local_families.include?(:ipv6)
+        end
+
+        # Whether this server has IPv4 connectivity. Defaults to true unless the
+        # host clearly only has IPv6, so that a host reporting no global
+        # addresses at all (e.g. inside a minimal container) still attempts IPv4
+        # as it did before this guard existed.
+        def ipv4_supported?
+          return @ipv4_supported unless @ipv4_supported.nil?
+
+          families = local_families
+          @ipv4_supported = families.include?(:ipv4) || !families.include?(:ipv6)
+        end
+
+        private
+
+        def local_families
+          families = []
+          Socket.ip_address_list.each do |address|
+            families << :ipv4 if address.ipv4? && !address.ipv4_loopback?
+            families << :ipv6 if address.ipv6? && !address.ipv6_loopback? && !address.ipv6_linklocal?
+          end
+          families.uniq
+        end
+
+      end
+
+      # @param [String] host
+      def initialize(host)
+        @host = host.to_s
+      end
+
+      def safe_connect_address
+        if @host.empty?
+          raise BlockedDestinationError, "No host was given for the request"
+        end
+
+        addresses = resolve
+        if addresses.empty?
+          raise BlockedDestinationError, "Could not resolve '#{@host}' to any IP address"
+        end
+
+        # Reject the whole request if *any* resolved address is blocked. This is
+        # checked before the reachability filtering below so that a blocked
+        # destination is always reported as such, regardless of which address
+        # families this particular server can reach. It also defeats DNS
+        # responses that mix a public and a private address to slip past.
+        addresses.each do |address|
+          next unless blocked?(address)
+
+          raise BlockedDestinationError,
+                "Destination '#{@host}' (#{address}) is not permitted"
+        end
+
+        # Only connect to an address whose family this server can actually
+        # reach. Otherwise we might pin the connection to an IPv6 address on a
+        # host without IPv6 connectivity and fail to connect even when a usable
+        # IPv4 address was available.
+        usable = addresses.select { |address| family_reachable?(address) }
+        if usable.empty?
+          raise SocketError,
+                "'#{@host}' only resolves to addresses this server cannot reach " \
+                "(#{addresses.join(', ')})"
+        end
+
+        # Prefer IPv4 for predictability; only use IPv6 when it is the only
+        # reachable option.
+        (usable.find(&:ipv4?) || usable.first).to_s
+      end
+
+      private
+
+      # @return [Array<IPAddr>]
+      def resolve
+        return [IPAddr.new(@host)] if ip_literal?
+
+        Resolv.getaddresses(@host).filter_map do |address|
+          IPAddr.new(address)
+        rescue IPAddr::InvalidAddressError
+          nil
+        end
+      end
+
+      def ip_literal?
+        IPAddr.new(@host)
+        true
+      rescue IPAddr::InvalidAddressError
+        false
+      end
+
+      # @param [IPAddr] address
+      def family_reachable?(address)
+        if address.ipv6? && !address.ipv4_mapped?
+          self.class.ipv6_supported?
+        else
+          self.class.ipv4_supported?
+        end
+      end
+
+      # @param [IPAddr] address
+      def blocked?(address)
+        return false if allowlisted?(address)
+
+        # IPv4-mapped IPv6 addresses (::ffff:a.b.c.d) must be checked against the
+        # IPv4 rules using the embedded address, otherwise they bypass the list.
+        if address.ipv6? && address.ipv4_mapped?
+          mapped = address.native
+          return true if mapped.ipv4? && BLOCKED_RANGES.any? { |range| range.include?(mapped) }
+        end
+
+        BLOCKED_RANGES.any? { |range| range.include?(address) }
+      end
+
+      # @param [IPAddr] address
+      def allowlisted?(address)
+        allowlist.any? do |entry|
+          if entry.is_a?(IPAddr)
+            entry.include?(address)
+          else
+            entry.casecmp?(@host)
+          end
+        end
+      end
+
+      # Allowlist entries are kept as strings in config. An entry that parses as
+      # an IP/CIDR is matched against the resolved address; anything else is
+      # matched against the request hostname (case-insensitively).
+      #
+      # @return [Array<IPAddr, String>]
+      def allowlist
+        @allowlist ||= Array(Postal::Config.postal.allowed_request_destinations).map do |entry|
+          IPAddr.new(entry.to_s)
+        rescue IPAddr::InvalidAddressError
+          entry.to_s
+        end
+      end
+
+    end
+  end
+end
diff --git a/lib/postal/http/blocked_destination_error.rb b/lib/postal/http/blocked_destination_error.rb
new file mode 100644
index 0000000..c08a444
--- /dev/null
+++ b/lib/postal/http/blocked_destination_error.rb
@@ -0,0 +1,11 @@
+# frozen_string_literal: true
+
+module Postal
+  module HTTP
+    # Raised when an outbound request would be sent to an address that is not
+    # permitted (a private, loopback, link-local or otherwise reserved address
+    # that has not been explicitly allowlisted). Used as an SSRF guard.
+    class BlockedDestinationError < StandardError
+    end
+  end
+end
diff --git a/spec/lib/postal/http/address_guard_spec.rb b/spec/lib/postal/http/address_guard_spec.rb
new file mode 100644
index 0000000..662534b
--- /dev/null
+++ b/spec/lib/postal/http/address_guard_spec.rb
@@ -0,0 +1,190 @@
+# frozen_string_literal: true
+
+require "rails_helper"
+
+RSpec.describe Postal::HTTP::AddressGuard do
+  describe ".safe_connect_address" do
+    subject(:call) { described_class.safe_connect_address(host) }
+
+    before do
+      allow(Postal::Config.postal).to receive(:allowed_request_destinations).and_return(allowlist)
+    end
+
+    let(:allowlist) { [] }
+
+    context "when given a public IP literal" do
+      let(:host) { "93.184.216.34" }
+
+      it "returns the address to connect to" do
+        expect(call).to eq "93.184.216.34"
+      end
+    end
+
+    context "when given a public IPv6 literal" do
+      let(:host) { "2606:2800:220:1:248:1893:25c8:1946" }
+
+      it "returns the address to connect to" do
+        expect(call).to eq "2606:2800:220:1:248:1893:25c8:1946"
+      end
+    end
+
+    [
+      "127.0.0.1",
+      "10.0.0.1",
+      "172.16.5.4",
+      "192.168.1.1",
+      "169.254.169.254", # cloud metadata
+      "100.64.0.1",      # carrier-grade NAT
+      "0.0.0.0",
+      "::1",
+      "fd00::1",         # unique-local IPv6
+      "fe80::1",         # link-local IPv6
+      "::ffff:127.0.0.1", # IPv4-mapped loopback
+    ].each do |blocked|
+      context "when given the blocked address #{blocked}" do
+        let(:host) { blocked }
+
+        it "raises BlockedDestinationError" do
+          expect { call }.to raise_error(Postal::HTTP::BlockedDestinationError)
+        end
+      end
+    end
+
+    context "when given a hostname that resolves to a public address" do
+      let(:host) { "example.com" }
+
+      before do
+        allow(Resolv).to receive(:getaddresses).with(host).and_return(["93.184.216.34"])
+      end
+
+      it "returns the resolved address" do
+        expect(call).to eq "93.184.216.34"
+      end
+    end
+
+    context "when given a hostname that resolves to a private address" do
+      let(:host) { "internal.example.com" }
+
+      before do
+        allow(Resolv).to receive(:getaddresses).with(host).and_return(["10.1.2.3"])
+      end
+
+      it "raises BlockedDestinationError" do
+        expect { call }.to raise_error(Postal::HTTP::BlockedDestinationError)
+      end
+    end
+
+    context "when a hostname resolves to both a public and a private address" do
+      let(:host) { "rebind.example.com" }
+
+      before do
+        allow(Resolv).to receive(:getaddresses).with(host).and_return(["93.184.216.34", "127.0.0.1"])
+      end
+
+      it "raises BlockedDestinationError because one address is blocked" do
+        expect { call }.to raise_error(Postal::HTTP::BlockedDestinationError)
+      end
+    end
+
+    context "when a hostname resolves to both IPv4 and IPv6 addresses" do
+      let(:host) { "dualstack.example.com" }
+      let(:ipv6) { "2606:2800:220:1:248:1893:25c8:1946" }
+
+      before do
+        allow(Resolv).to receive(:getaddresses).with(host).and_return([ipv6, "93.184.216.34"])
+      end
+
+      context "and the server does not support IPv6" do
+        before { allow(described_class).to receive(:ipv6_supported?).and_return(false) }
+
+        it "connects over IPv4" do
+          expect(call).to eq "93.184.216.34"
+        end
+      end
+
+      context "and the server supports IPv6" do
+        before { allow(described_class).to receive(:ipv6_supported?).and_return(true) }
+
+        it "still prefers IPv4 for predictability" do
+          expect(call).to eq "93.184.216.34"
+        end
+      end
+    end
+
+    context "when a hostname resolves only to an IPv6 address" do
+      let(:host) { "v6only.example.com" }
+      let(:ipv6) { "2606:2800:220:1:248:1893:25c8:1946" }
+
+      before do
+        allow(Resolv).to receive(:getaddresses).with(host).and_return([ipv6])
+      end
+
+      context "and the server does not support IPv6" do
+        before { allow(described_class).to receive(:ipv6_supported?).and_return(false) }
+
+        it "raises a SocketError because the address is unreachable" do
+          expect { call }.to raise_error(SocketError)
+        end
+      end
+
+      context "and the server supports IPv6" do
+        before { allow(described_class).to receive(:ipv6_supported?).and_return(true) }
+
+        it "connects over IPv6" do
+          expect(call).to eq ipv6
+        end
+      end
+    end
+
+    context "when a hostname cannot be resolved" do
+      let(:host) { "nope.example.com" }
+
+      before do
+        allow(Resolv).to receive(:getaddresses).with(host).and_return([])
+      end
+
+      it "raises BlockedDestinationError" do
+        expect { call }.to raise_error(Postal::HTTP::BlockedDestinationError, /resolve/)
+      end
+    end
+
+    context "when the host is blank" do
+      let(:host) { "" }
+
+      it "raises BlockedDestinationError" do
+        expect { call }.to raise_error(Postal::HTTP::BlockedDestinationError)
+      end
+    end
+
+    context "when a blocked address is allowlisted by CIDR" do
+      let(:host) { "10.0.0.5" }
+      let(:allowlist) { ["10.0.0.0/8"] }
+
+      it "returns the address" do
+        expect(call).to eq "10.0.0.5"
+      end
+    end
+
+    context "when a blocked address is allowlisted by exact IP" do
+      let(:host) { "127.0.0.1" }
+      let(:allowlist) { ["127.0.0.1"] }
+
+      it "returns the address" do
+        expect(call).to eq "127.0.0.1"
+      end
+    end
+
+    context "when a hostname resolving to a private address is allowlisted by name" do
+      let(:host) { "internal.example.com" }
+      let(:allowlist) { ["internal.example.com"] }
+
+      before do
+        allow(Resolv).to receive(:getaddresses).with(host).and_return(["10.1.2.3"])
+      end
+
+      it "returns the resolved address" do
+        expect(call).to eq "10.1.2.3"
+      end
+    end
+  end
+end
diff --git a/spec/lib/postal/http_spec.rb b/spec/lib/postal/http_spec.rb
new file mode 100644
index 0000000..ce90ff9
--- /dev/null
+++ b/spec/lib/postal/http_spec.rb
@@ -0,0 +1,80 @@
+# frozen_string_literal: true
+
+require "rails_helper"
+
+RSpec.describe Postal::HTTP do
+  before do
+    allow(Postal::Config.postal).to receive(:allowed_request_destinations).and_return([])
+  end
+
+  describe ".post" do
+    context "when the host resolves to a blocked address" do
+      before do
+        allow(Resolv).to receive(:getaddresses).with("internal.example.com").and_return(["127.0.0.1"])
+      end
+
+      it "does not make a request and returns a blocked-destination result" do
+        result = described_class.post("http://internal.example.com/hook", json: "{}")
+        expect(result[:code]).to eq(-4)
+        expect(result[:body]).to match(/not permitted/)
+        expect(WebMock).not_to have_requested(:post, "http://internal.example.com/hook")
+      end
+    end
+
+    context "when resolving the host raises an error" do
+      before do
+        allow(Resolv).to receive(:getaddresses).with("example.com").and_raise(Resolv::ResolvError, "resolver failed")
+      end
+
+      it "returns a connection error result" do
+        result = described_class.post("http://example.com/hook", json: "{}")
+        expect(result[:code]).to eq(-2)
+        expect(result[:body]).to match(/resolver failed/)
+        expect(WebMock).not_to have_requested(:post, "http://example.com/hook")
+      end
+    end
+
+    context "when resolving the host exceeds the request timeout" do
+      before do
+        allow(Resolv).to receive(:getaddresses).with("example.com") do
+          sleep 0.2
+          ["93.184.216.34"]
+        end
+      end
+
+      it "returns a timeout result before making a request" do
+        result = described_class.post("http://example.com/hook", json: "{}", timeout: 0.05)
+        expect(result[:code]).to eq(-1)
+        expect(WebMock).not_to have_requested(:post, "http://example.com/hook")
+      end
+    end
+
+    context "when the host resolves to a public address" do
+      before do
+        allow(Resolv).to receive(:getaddresses).with("example.com").and_return(["93.184.216.34"])
+        stub_request(:post, "http://example.com/hook").to_return(status: 200, body: "OK")
+      end
+
+      it "pins the connection to the validated address and performs the request" do
+        expect_any_instance_of(Net::HTTP).to receive(:ipaddr=).with("93.184.216.34").and_call_original
+        result = described_class.post("http://example.com/hook", json: "{}")
+        expect(result[:code]).to eq(200)
+        expect(WebMock).to have_requested(:post, "http://example.com/hook")
+      end
+    end
+
+    context "when the blocked host is allowlisted" do
+      before do
+        allow(Postal::Config.postal).to receive(:allowed_request_destinations).and_return(["internal.example.com"])
+        allow(Resolv).to receive(:getaddresses).with("internal.example.com").and_return(["10.0.0.5"])
+        stub_request(:post, "http://internal.example.com/hook").to_return(status: 200, body: "OK")
+      end
+
+      it "performs the request" do
+        result = described_class.post("http://internal.example.com/hook", json: "{}")
+        expect(result[:code]).to eq(200)
+        expect(WebMock).to have_requested(:post, "http://internal.example.com/hook")
+      end
+    end
+  end
+end
diff --git a/spec/models/http_endpoint_spec.rb b/spec/models/http_endpoint_spec.rb
new file mode 100644
index 0000000..37a6881
--- /dev/null
+++ b/spec/models/http_endpoint_spec.rb
@@ -0,0 +1,38 @@
+# frozen_string_literal: true
+
+require "rails_helper"
+
+RSpec.describe HTTPEndpoint do
+  describe "validations" do
+    subject(:endpoint) { build(:http_endpoint, url: url) }
+
+    [
+      "https://example.com/messages/~user;v=1?token=a+b#section",
+      "http://example.com:8080/path?x=1&y=2",
+      "https://[2606:2800:220:1:248:1893:25c8:1946]/hook",
+    ].each do |valid_url|
+      context "with #{valid_url}" do
+        let(:url) { valid_url }
+
+        it "is valid" do
+          expect(endpoint).to be_valid
+        end
+      end
+    end
+
+    [
+      "ftp://example.com/hook",
+      "https:///missing-host",
+      "not a url",
+    ].each do |invalid_url|
+      context "with #{invalid_url}" do
+        let(:url) { invalid_url }
+
+        it "is invalid" do
+          expect(endpoint).not_to be_valid
+          expect(endpoint.errors[:url]).to be_present
+        end
+      end
+    end
+  end
+end
diff --git a/spec/services/webhook_delivery_service_spec.rb b/spec/services/webhook_delivery_service_spec.rb
index 14b0f59..14a9fa2 100644
--- a/spec/services/webhook_delivery_service_spec.rb
+++ b/spec/services/webhook_delivery_service_spec.rb
@@ -13,6 +13,7 @@ RSpec.describe WebhookDeliveryService do
   let(:response_body) { "OK" }
 
   before do
+    allow(Resolv).to receive(:getaddresses).with("example.com").and_return(["93.184.216.34"])
     stub_request(:post, webhook.url).to_return(status: response_status, body: response_body)
   end
 
@@ -116,5 +117,26 @@ RSpec.describe WebhookDeliveryService do
         expect { webhook_request.reload }.to raise_error(ActiveRecord::RecordNotFound)
       end
     end
+
+    context "when the webhook URL resolves to a blocked (private) address" do
+      let(:webhook_request) do
+        create(:webhook_request, :locked, webhook: webhook, url: "http://internal.example.com/hook")
+      end
+
+      before do
+        allow(Resolv).to receive(:getaddresses).with("internal.example.com").and_return(["127.0.0.1"])
+      end
+
+      it "does not make a request to the destination" do
+        service.call
+        expect(WebMock).not_to have_requested(:post, "http://internal.example.com/hook")
+      end
+
+      it "records the failure and schedules a retry" do
+        service.call
+        expect(webhook_request.reload.attempts).to eq(1)
+        expect(webhook_request.retry_after).to be_present
+      end
+    end
   end
 end