diff --git a/config.go b/config.go
index 7053c12..c92bd63 100644
--- a/config.go
+++ b/config.go
@@ -8,6 +8,7 @@ import (
 	"strconv"
 	"strings"
 
+	"github.com/hrfee/jfa-go/easyproxy"
 	"gopkg.in/ini.v1"
 )
 
@@ -135,6 +136,22 @@ func (app *appContext) loadConfig() error {
 		messagesEnabled = false
 	}
 
+	if app.proxyEnabled = app.config.Section("advanced").Key("proxy").MustBool(false); app.proxyEnabled {
+		app.proxyConfig = easyproxy.ProxyConfig{}
+		app.proxyConfig.Protocol = easyproxy.HTTP
+		if strings.Contains(app.config.Section("advanced").Key("proxy_protocol").MustString("http"), "socks") {
+			app.proxyConfig.Protocol = easyproxy.SOCKS5
+		}
+		app.proxyConfig.Addr = app.config.Section("advanced").Key("proxy_address").MustString("")
+		app.proxyConfig.User = app.config.Section("advanced").Key("proxy_user").MustString("")
+		app.proxyConfig.Password = app.config.Section("advanced").Key("proxy_password").MustString("")
+		app.proxyTransport, err = easyproxy.NewTransport(app.proxyConfig)
+		if err != nil {
+			app.err.Printf("Failed to initialize Proxy: %v\n", err)
+		}
+		app.proxyEnabled = true
+	}
+
 	app.MustSetValue("updates", "enabled", "true")
 	releaseChannel := app.config.Section("updates").Key("channel").String()
 	if app.config.Section("updates").Key("enabled").MustBool(false) {
@@ -147,6 +164,9 @@ func (app *appContext) loadConfig() error {
 			v = "git"
 		}
 		app.updater = newUpdater(baseURL, namespace, repo, v, commit, updater)
+		if app.proxyEnabled {
+			app.updater.SetTransport(app.proxyTransport)
+		}
 	}
 	if releaseChannel == "" {
 		if version == "git" {
diff --git a/easyproxy/easyproxy.go b/easyproxy/easyproxy.go
index b9c9bba..ef6557b 100644
--- a/easyproxy/easyproxy.go
+++ b/easyproxy/easyproxy.go
@@ -1,10 +1,12 @@
-// Package easyproxy provides a method to quickly create a http.Transport using given proxy details (SOCKS5 or HTTP).
+// Package easyproxy provides a method to quickly create a http.Transport or net.Conn using given proxy details (SOCKS5 or HTTP).
 package easyproxy
 
 import (
+	"crypto/tls"
 	"net/http"
 	"net/url"
 
+	"github.com/magisterquis/connectproxy"
 	"golang.org/x/net/proxy"
 )
 
@@ -15,28 +17,67 @@ const (
 	HTTP                   // HTTP
 )
 
+type ProxyConfig struct {
+	Protocol Protocol
+	Addr     string
+	User     string
+	Password string
+}
+
 // NewTransport returns a http.Transport using the given proxy details. Leave user/pass blank if not needed.
-func NewTransport(p Protocol, addr, user, pass string) (*http.Transport, error) {
+func NewTransport(c ProxyConfig) (*http.Transport, error) {
 	t := &http.Transport{}
-	if p == HTTP {
+	if c.Protocol == HTTP {
 		u := &url.URL{
 			Scheme: "http",
-			Host:   addr,
+			Host:   c.Addr,
 		}
-		if user != "" && pass != "" {
-			u.User = url.UserPassword(user, pass)
+		if c.User != "" && c.Password != "" {
+			u.User = url.UserPassword(c.User, c.Password)
 		}
 		t.Proxy = http.ProxyURL(u)
 		return t, nil
 	}
 	var auth *proxy.Auth = nil
-	if user != "" && pass != "" {
-		auth = &proxy.Auth{User: user, Password: pass}
+	if c.User != "" && c.Password != "" {
+		auth = &proxy.Auth{User: c.User, Password: c.Password}
 	}
-	dialer, err := proxy.SOCKS5("tcp", addr, auth, proxy.Direct)
+	dialer, err := proxy.SOCKS5("tcp", c.Addr, auth, proxy.Direct)
 	if err != nil {
-		return nil, nil
+		return nil, err
 	}
 	t.Dial = dialer.Dial
 	return t, nil
 }
+
+// NewConn returns a tls.Conn to "addr" using the given proxy details. Leave user/pass blank if not needed.
+func NewConn(c ProxyConfig, addr string, tlsConf *tls.Config) (*tls.Conn, error) {
+	var proxyDialer proxy.Dialer
+	var err error
+	if c.Protocol == SOCKS5 {
+		var auth *proxy.Auth = nil
+		if c.User != "" && c.Password != "" {
+			auth = &proxy.Auth{User: c.User, Password: c.Password}
+		}
+		proxyDialer, err = proxy.SOCKS5("tcp", c.Addr, auth, proxy.Direct)
+		if err != nil {
+			return nil, err
+		}
+	} else {
+		u := &url.URL{
+			Scheme: "http",
+			Host:   c.Addr,
+		}
+		if c.User != "" && c.Password != "" {
+			u.User = url.UserPassword(c.User, c.Password)
+		}
+		proxyDialer, err = connectproxy.New(u, proxy.Direct)
+	}
+
+	dialer, err := proxyDialer.Dial("tcp", addr)
+	if err != nil {
+		return nil, err
+	}
+	conn := tls.Client(dialer, tlsConf)
+	return conn, nil
+}
diff --git a/easyproxy/go.mod b/easyproxy/go.mod
index d2c531f..f88550a 100644
--- a/easyproxy/go.mod
+++ b/easyproxy/go.mod
@@ -3,3 +3,5 @@ module github.com/hrfee/jfa-go/easyproxy
 go 1.20
 
 require golang.org/x/net v0.15.0
+
+require github.com/magisterquis/connectproxy v0.0.0-20200725203833-3582e84f0c9b // indirect
diff --git a/easyproxy/go.sum b/easyproxy/go.sum
index 9746d02..a131b72 100644
--- a/easyproxy/go.sum
+++ b/easyproxy/go.sum
@@ -1,2 +1,4 @@
+github.com/magisterquis/connectproxy v0.0.0-20200725203833-3582e84f0c9b h1:xZ59n7Frzh8CwyfAapUZLSg+gXH5m63YEaFCMpDHhpI=
+github.com/magisterquis/connectproxy v0.0.0-20200725203833-3582e84f0c9b/go.mod h1:uDd4sYVYsqcxAB8j+Q7uhL6IJCs/r1kxib1HV4bgOMg=
 golang.org/x/net v0.15.0 h1:ugBLEUaxABaB5AJqW9enI0ACdci2RUd4eP51NTBvuJ8=
 golang.org/x/net v0.15.0/go.mod h1:idbUs1IY1+zTqbi8yxTbhexhEEk5ur9LInksu6HrEpk=
diff --git a/email.go b/email.go
index 0f517ca..9671ee4 100644
--- a/email.go
+++ b/email.go
@@ -19,6 +19,7 @@ import (
 
 	"github.com/gomarkdown/markdown"
 	"github.com/gomarkdown/markdown/html"
+	"github.com/hrfee/jfa-go/easyproxy"
 	"github.com/hrfee/mediabrowser"
 	"github.com/itchyny/timefmt-go"
 	"github.com/mailgun/mailgun-go/v4"
@@ -87,7 +88,11 @@ func NewEmailer(app *appContext) *Emailer {
 		if username == "" && password != "" {
 			username = emailer.fromAddr
 		}
-		err := emailer.NewSMTP(app.config.Section("smtp").Key("server").String(), app.config.Section("smtp").Key("port").MustInt(465), username, password, sslTLS, app.config.Section("smtp").Key("ssl_cert").MustString(""), app.config.Section("smtp").Key("hello_hostname").String(), app.config.Section("smtp").Key("cert_validation").MustBool(true))
+		var proxyConf *easyproxy.ProxyConfig = nil
+		if app.proxyEnabled {
+			proxyConf = &app.proxyConfig
+		}
+		err := emailer.NewSMTP(app.config.Section("smtp").Key("server").String(), app.config.Section("smtp").Key("port").MustInt(465), username, password, sslTLS, app.config.Section("smtp").Key("ssl_cert").MustString(""), app.config.Section("smtp").Key("hello_hostname").String(), app.config.Section("smtp").Key("cert_validation").MustBool(true), proxyConf)
 		if err != nil {
 			app.err.Printf("Error while initiating SMTP mailer: %v", err)
 		}
@@ -113,7 +118,7 @@ type SMTP struct {
 }
 
 // NewSMTP returns an SMTP emailClient.
-func (emailer *Emailer) NewSMTP(server string, port int, username, password string, sslTLS bool, certPath string, helloHostname string, validateCertificate bool) (err error) {
+func (emailer *Emailer) NewSMTP(server string, port int, username, password string, sslTLS bool, certPath string, helloHostname string, validateCertificate bool, proxy *easyproxy.ProxyConfig) (err error) {
 	sender := &SMTP{}
 	sender.Client = sMail.NewSMTPClient()
 	if sslTLS {
@@ -131,12 +136,16 @@ func (emailer *Emailer) NewSMTP(server string, port int, username, password stri
 	sender.Client.Host = server
 	sender.Client.Port = port
 	sender.Client.KeepAlive = false
+
 	// x509.SystemCertPool is unavailable on windows
 	if PLATFORM == "windows" {
 		sender.Client.TLSConfig = &tls.Config{
 			InsecureSkipVerify: !validateCertificate,
 			ServerName:         server,
 		}
+		if proxy != nil {
+			sender.Client.CustomConn, err = easyproxy.NewConn(*proxy, fmt.Sprintf("%s:%d", server, port), sender.Client.TLSConfig)
+		}
 		emailer.sender = sender
 		return
 	}
@@ -156,6 +165,9 @@ func (emailer *Emailer) NewSMTP(server string, port int, username, password stri
 		ServerName:         server,
 		RootCAs:            rootCAs,
 	}
+	if proxy != nil {
+		sender.Client.CustomConn, err = easyproxy.NewConn(*proxy, fmt.Sprintf("%s:%d", server, port), sender.Client.TLSConfig)
+	}
 	emailer.sender = sender
 	return
 }
diff --git a/go.mod b/go.mod
index c4650b4..f2866a2 100644
--- a/go.mod
+++ b/go.mod
@@ -43,7 +43,7 @@ require (
 	github.com/swaggo/gin-swagger v1.6.0
 	github.com/timshannon/badgerhold/v4 v4.0.2
 	github.com/writeas/go-strip-markdown v2.0.1+incompatible
-	github.com/xhit/go-simple-mail/v2 v2.13.0
+	github.com/xhit/go-simple-mail/v2 v2.16.0
 	gopkg.in/ini.v1 v1.67.0
 	maunium.net/go/mautrix v0.15.3
 )
@@ -93,6 +93,7 @@ require (
 	github.com/klauspost/compress v1.16.6 // indirect
 	github.com/klauspost/cpuid/v2 v2.2.5 // indirect
 	github.com/leodido/go-urn v1.2.4 // indirect
+	github.com/magisterquis/connectproxy v0.0.0-20200725203833-3582e84f0c9b // indirect
 	github.com/mailru/easyjson v0.7.7 // indirect
 	github.com/mattn/go-colorable v0.1.13 // indirect
 	github.com/mattn/go-isatty v0.0.19 // indirect
diff --git a/go.sum b/go.sum
index 85f8f14..07de685 100644
--- a/go.sum
+++ b/go.sum
@@ -264,6 +264,8 @@ github.com/lithammer/shortuuid/v3 v3.0.7/go.mod h1:vMk8ke37EmiewwolSO1NLW8vP4ZaK
 github.com/lxn/walk v0.0.0-20210112085537-c389da54e794/go.mod h1:E23UucZGqpuUANJooIbHWCufXvOcT6E7Stq81gU+CSQ=
 github.com/lxn/win v0.0.0-20210218163916-a377121e959e/go.mod h1:KxxjdtRkfNoYDCUP5ryK7XJJNTnpC8atvtmTheChOtk=
 github.com/magiconair/properties v1.8.0/go.mod h1:PppfXfuXeibc/6YijjN8zIbojt8czPbwD3XqdrwzmxQ=
+github.com/magisterquis/connectproxy v0.0.0-20200725203833-3582e84f0c9b h1:xZ59n7Frzh8CwyfAapUZLSg+gXH5m63YEaFCMpDHhpI=
+github.com/magisterquis/connectproxy v0.0.0-20200725203833-3582e84f0c9b/go.mod h1:uDd4sYVYsqcxAB8j+Q7uhL6IJCs/r1kxib1HV4bgOMg=
 github.com/mailgun/mailgun-go/v4 v4.9.1 h1:D/jhJXYod4RqRsNOOSrjrtAcMEnz8mPYJmeA5cueHKY=
 github.com/mailgun/mailgun-go/v4 v4.9.1/go.mod h1:FJlF9rI5cQT+mrwujtJjPMbIVy3Ebor9bKTVsJ0QU40=
 github.com/mailru/easyjson v0.0.0-20180823135443-60711f1a8329/go.mod h1:C1wdFJiN94OJF2b5HbByQZoLdCWB1Yqtg26g4irojpc=
@@ -394,6 +396,8 @@ github.com/writeas/go-strip-markdown v2.0.1+incompatible h1:IIqxTM5Jr7RzhigcL6Fk
 github.com/writeas/go-strip-markdown v2.0.1+incompatible/go.mod h1:Rsyu10ZhbEK9pXdk8V6MVnZmTzRG0alMNLMwa0J01fE=
 github.com/xhit/go-simple-mail/v2 v2.13.0 h1:OANWU9jHZrVfBkNkvLf8Ww0fexwpQVF/v/5f96fFTLI=
 github.com/xhit/go-simple-mail/v2 v2.13.0/go.mod h1:b7P5ygho6SYE+VIqpxA6QkYfv4teeyG4MKqB3utRu98=
+github.com/xhit/go-simple-mail/v2 v2.16.0 h1:ouGy/Ww4kuaqu2E2UrDw7SvLaziWTB60ICLkIkNVccA=
+github.com/xhit/go-simple-mail/v2 v2.16.0/go.mod h1:b7P5ygho6SYE+VIqpxA6QkYfv4teeyG4MKqB3utRu98=
 github.com/xordataexchange/crypt v0.0.3-0.20170626215501-b2862e3d0a77/go.mod h1:aYKd//L2LvnjZzWKhF00oedf4jCCReLcmhLdhm1A27Q=
 github.com/yuin/goldmark v1.1.27/go.mod h1:3hX8gzYuyVAZsxl0MRgGTJEmQBFcNTphYh9decYSb74=
 github.com/yuin/goldmark v1.2.1/go.mod h1:3hX8gzYuyVAZsxl0MRgGTJEmQBFcNTphYh9decYSb74=
diff --git a/main.go b/main.go
index 45ed009..8156edf 100644
--- a/main.go
+++ b/main.go
@@ -114,6 +114,9 @@ type appContext struct {
 	newUpdate            bool // Whether whatever's in update is new.
 	tag                  Tag
 	update               Update
+	proxyEnabled         bool
+	proxyTransport       *http.Transport
+	proxyConfig          easyproxy.ProxyConfig
 	internalPWRs         map[string]InternalPWR
 	ConfirmationKeys     map[string]map[string]newUserDTO // Map of invite code to jwt to request
 	confirmationKeysLock sync.Mutex
@@ -392,20 +395,8 @@ func start(asDaemon, firstCall bool) {
 			app.jf.Verbose = true
 		}
 
-		if app.config.Section("advanced").Key("proxy").MustBool(false) {
-			// FIXME: Use Proxy
-			protocol := easyproxy.HTTP
-			if strings.Contains(app.config.Section("advanced").Key("proxy_protocol").MustString("http"), "socks") {
-				protocol = easyproxy.SOCKS5
-			}
-			addr := app.config.Section("advanced").Key("proxy_address").MustString("")
-			user := app.config.Section("advanced").Key("proxy_user").MustString("")
-			password := app.config.Section("advanced").Key("proxy_password").MustString("")
-			transport, err := easyproxy.NewTransport(protocol, addr, user, password)
-			if err != nil {
-				app.err.Printf("Failed to initialize Proxy: %v\n", err)
-			}
-			app.jf.SetTransport(transport)
+		if app.proxyEnabled {
+			app.jf.SetTransport(app.proxyTransport)
 		}
 
 		var status int
diff --git a/updater.go b/updater.go
index c6c8c62..1e0e78a 100644
--- a/updater.go
+++ b/updater.go
@@ -185,6 +185,11 @@ type BuildDTO struct {
 	Tags    map[string]Tag
 }
 
+// SetTransport sets the http.Transport to use for requests. Can be used to set a proxy.
+func (ud *Updater) SetTransport(t *http.Transport) {
+	ud.httpClient.Transport = t
+}
+
 func (ud *Updater) GetTag() (Tag, int, error) {
 	if ud.buildType == off {
 		return Tag{}, -1, nil