diff --git a/server/configs/http-c2.go b/server/configs/http-c2.go
index b10e7ddd68..6de0116b60 100644
--- a/server/configs/http-c2.go
+++ b/server/configs/http-c2.go
@@ -21,7 +21,6 @@ package configs
 import (
 	"errors"
 	"fmt"
-	insecureRand "math/rand"
 	"regexp"
 	"strings"
 
@@ -40,84 +39,6 @@ type HTTPC2Config struct {
 	ServerConfig  *HTTPC2ServerConfig  `json:"server_config"`
 }
 
-// RandomImplantConfig - Randomly generate a new implant config from the parent config,
-// this is the primary configuration used by the implant generation.
-func (h *HTTPC2Config) RandomImplantConfig() *HTTPC2ImplantConfig {
-	return &HTTPC2ImplantConfig{
-
-		NonceQueryArgChars: h.ImplantConfig.NonceQueryArgChars,
-		URLParameters:      h.ImplantConfig.URLParameters,
-		Headers:            h.ImplantConfig.Headers,
-
-		PollFileExt: h.ImplantConfig.PollFileExt,
-		PollFiles:   h.ImplantConfig.RandomPollFiles(),
-		PollPaths:   h.ImplantConfig.RandomPollPaths(),
-
-		StartSessionFileExt: h.ImplantConfig.StartSessionFileExt,
-		SessionFileExt:      h.ImplantConfig.SessionFileExt,
-		SessionFiles:        h.ImplantConfig.RandomSessionFiles(),
-		SessionPaths:        h.ImplantConfig.RandomSessionPaths(),
-
-		CloseFileExt: h.ImplantConfig.CloseFileExt,
-		CloseFiles:   h.ImplantConfig.RandomCloseFiles(),
-		ClosePaths:   h.ImplantConfig.RandomClosePaths(),
-	}
-}
-
-// GenerateUserAgent - Generate a user-agent depending on OS/Arch
-func (h *HTTPC2Config) GenerateUserAgent(goos string, goarch string) string {
-	return h.generateChromeUserAgent(goos, goarch)
-}
-
-func (h *HTTPC2Config) generateChromeUserAgent(goos string, goarch string) string {
-	if h.ImplantConfig.UserAgent == "" {
-		switch goos {
-		case "windows":
-			switch goarch {
-			case "amd64":
-				return fmt.Sprintf("Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/%s Safari/537.36", h.ChromeVer())
-			}
-
-		case "linux":
-			switch goarch {
-			case "amd64":
-				return fmt.Sprintf("Mozilla/5.0 (X11; Linux x86_64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/%s Safari/537.36", h.ChromeVer())
-			}
-
-		case "darwin":
-			switch goarch {
-			case "arm64":
-				fallthrough // https://source.chromium.org/chromium/chromium/src/+/master:third_party/blink/renderer/core/frame/navigator_id.cc;l=76
-			case "amd64":
-				return fmt.Sprintf("Mozilla/5.0 (Macintosh; Intel Mac OS X %s) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/%s Safari/537.36", h.MacOSVer(), h.ChromeVer())
-			}
-
-		}
-	} else {
-		return h.ImplantConfig.UserAgent
-	}
-
-	// Default is a generic Windows/Chrome
-	return fmt.Sprintf("Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/%s Safari/537.36", h.ChromeVer())
-}
-
-// ChromeVer - Generate a random Chrome user-agent
-func (h *HTTPC2Config) ChromeVer() string {
-	chromeVer := h.ImplantConfig.ChromeBaseVersion
-	if chromeVer == 0 {
-		chromeVer = DefaultChromeBaseVer
-	}
-	return fmt.Sprintf("%d.0.%d.%d", chromeVer+insecureRand.Intn(3), 1000+insecureRand.Intn(8999), insecureRand.Intn(999))
-}
-
-func (h *HTTPC2Config) MacOSVer() string {
-	macosVer := h.ImplantConfig.MacOSVersion
-	if macosVer == "" {
-		macosVer = DefaultMacOSVer
-	}
-	return macosVer
-}
-
 // HTTPC2ServerConfig - Server configuration options
 type HTTPC2ServerConfig struct {
 	RandomVersionHeaders bool                   `json:"random_version_headers"`
@@ -177,58 +98,6 @@ type HTTPC2ImplantConfig struct {
 	ClosePaths   []string `json:"close_paths"`
 }
 
-func (h *HTTPC2ImplantConfig) RandomPollFiles() []string {
-	min := h.MinFiles
-	if min < 1 {
-		min = 1
-	}
-	return h.randomSample(h.PollFiles, h.PollFileExt, min, h.MaxFiles)
-}
-
-func (h *HTTPC2ImplantConfig) RandomPollPaths() []string {
-	return h.randomSample(h.PollPaths, "", h.MinPaths, h.MaxPaths)
-}
-
-func (h *HTTPC2ImplantConfig) RandomCloseFiles() []string {
-	min := h.MinFiles
-	if min < 1 {
-		min = 1
-	}
-	return h.randomSample(h.CloseFiles, h.CloseFileExt, min, h.MaxFiles)
-}
-
-func (h *HTTPC2ImplantConfig) RandomClosePaths() []string {
-	return h.randomSample(h.ClosePaths, "", h.MinPaths, h.MaxPaths)
-}
-
-func (h *HTTPC2ImplantConfig) RandomSessionFiles() []string {
-	min := h.MinFiles
-	if min < 1 {
-		min = 1
-	}
-	return h.randomSample(h.SessionFiles, h.SessionFileExt, min, h.MaxFiles)
-}
-
-func (h *HTTPC2ImplantConfig) RandomSessionPaths() []string {
-	return h.randomSample(h.SessionPaths, "", h.MinPaths, h.MaxPaths)
-}
-
-func (h *HTTPC2ImplantConfig) randomSample(values []string, ext string, min int, max int) []string {
-	count := insecureRand.Intn(len(values))
-	if count < min {
-		count = min
-	}
-	if max < count {
-		count = max
-	}
-	sample := []string{}
-	for i := 0; len(sample) < count; i++ {
-		index := (count + i) % len(values)
-		sample = append(sample, values[index])
-	}
-	return sample
-}
-
 // CheckHTTPC2ConfigErrors - Get the current HTTP C2 config
 func CheckHTTPC2ConfigErrors(config *clientpb.HTTPC2Config) error {
 	err := checkHTTPC2Config(config)
diff --git a/server/db/models/http-c2.go b/server/db/models/http-c2.go
index bc98684cd5..84d3cc2097 100644
--- a/server/db/models/http-c2.go
+++ b/server/db/models/http-c2.go
@@ -19,13 +19,21 @@ package models
 */
 
 import (
+	"fmt"
 	"time"
 
 	"github.com/bishopfox/sliver/protobuf/clientpb"
 	"github.com/gofrs/uuid"
+	insecureRand "math/rand"
+
 	"gorm.io/gorm"
 )
 
+const (
+	DefaultChromeBaseVer = 106
+	DefaultMacOSVer      = "10_15_7"
+)
+
 // HttpC2Config -
 type HttpC2Config struct {
 	ID        uuid.UUID `gorm:"primaryKey;->;<-:create;type:uuid;"`
@@ -351,3 +359,155 @@ func HTTPC2ConfigFromProtobuf(pbHttpC2Config *clientpb.HTTPC2Config) *HttpC2Conf
 
 	return cfg
 }
+
+// RandomImplantConfig - Randomly generate a new implant config from the parent config,
+// this is the primary configuration used by the implant generation.
+func RandomizeImplantConfig(h *clientpb.HTTPC2ImplantConfig, goos string, goarch string) *clientpb.HTTPC2ImplantConfig {
+	return &clientpb.HTTPC2ImplantConfig{
+
+		NonceQueryArgChars: h.NonceQueryArgChars,
+		ExtraURLParameters: h.ExtraURLParameters,
+		Headers:            h.Headers,
+
+		PollFileExtension:         h.PollFileExtension,
+		StartSessionFileExtension: h.StartSessionFileExtension,
+		SessionFileExtension:      h.SessionFileExtension,
+		CloseFileExtension:        h.CloseFileExtension,
+		PathSegments:              RandomPathSegments(h),
+		UserAgent:                 GenerateUserAgent(goos, goarch, h.UserAgent, h.ChromeBaseVersion, h.MacOSVersion),
+	}
+}
+
+// GenerateUserAgent - Generate a user-agent depending on OS/Arch
+func GenerateUserAgent(goos string, goarch string, userAgent string, baseVer int32, macOsVer string) string {
+	return generateChromeUserAgent(goos, goarch, userAgent, baseVer, macOsVer)
+}
+
+func generateChromeUserAgent(goos string, goarch string, userAgent string, baseVer int32, macOsVer string) string {
+	if userAgent == "" {
+		switch goos {
+		case "windows":
+			switch goarch {
+			case "amd64":
+				return fmt.Sprintf("Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/%s Safari/537.36", ChromeVer(baseVer))
+			}
+
+		case "linux":
+			switch goarch {
+			case "amd64":
+				return fmt.Sprintf("Mozilla/5.0 (X11; Linux x86_64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/%s Safari/537.36", ChromeVer(baseVer))
+			}
+
+		case "darwin":
+			switch goarch {
+			case "arm64":
+				fallthrough // https://source.chromium.org/chromium/chromium/src/+/master:third_party/blink/renderer/core/frame/navigator_id.cc;l=76
+			case "amd64":
+				return fmt.Sprintf("Mozilla/5.0 (Macintosh; Intel Mac OS X %s) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/%s Safari/537.36", MacOSVer(macOsVer), ChromeVer(baseVer))
+			}
+
+		}
+	} else {
+		return userAgent
+	}
+
+	// Default is a generic Windows/Chrome
+	return fmt.Sprintf("Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/%s Safari/537.36", ChromeVer(baseVer))
+}
+
+// ChromeVer - Generate a random Chrome user-agent
+func ChromeVer(baseVer int32) string {
+	chromeVer := baseVer
+	if chromeVer == 0 {
+		chromeVer = DefaultChromeBaseVer
+	}
+	return fmt.Sprintf("%d.0.%d.%d", baseVer+int32(insecureRand.Intn(3)), 1000+int32(insecureRand.Intn(8999)), int32(insecureRand.Intn(999)))
+}
+
+func MacOSVer(MacOSVersion string) string {
+	macosVer := MacOSVersion
+	if macosVer == "" {
+		macosVer = DefaultMacOSVer
+	}
+	return macosVer
+}
+
+func RandomPathSegments(h *clientpb.HTTPC2ImplantConfig) []*clientpb.HTTPC2PathSegment {
+
+	var (
+		sessionPaths []*clientpb.HTTPC2PathSegment
+		closePaths   []*clientpb.HTTPC2PathSegment
+		pollPaths    []*clientpb.HTTPC2PathSegment
+		sessionFiles []*clientpb.HTTPC2PathSegment
+		closeFiles   []*clientpb.HTTPC2PathSegment
+		pollFiles    []*clientpb.HTTPC2PathSegment
+	)
+	for _, pathSegment := range h.PathSegments {
+		switch pathSegment.SegmentType {
+		case 0:
+			if pathSegment.IsFile {
+				pollFiles = append(pollFiles, pathSegment)
+			} else {
+				pollPaths = append(pollPaths, pathSegment)
+			}
+		case 1:
+			if pathSegment.IsFile {
+				sessionFiles = append(sessionFiles, pathSegment)
+			} else {
+				sessionPaths = append(sessionPaths, pathSegment)
+			}
+		case 2:
+			if pathSegment.IsFile {
+				closeFiles = append(closeFiles, pathSegment)
+			} else {
+				closePaths = append(closePaths, pathSegment)
+			}
+		default:
+			continue
+		}
+	}
+
+	sessionPaths = RandomPaths(sessionPaths, h.MinPaths, h.MaxPaths)
+	pollPaths = RandomPaths(pollPaths, h.MinPaths, h.MaxPaths)
+	closePaths = RandomPaths(closePaths, h.MinPaths, h.MaxPaths)
+
+	sessionFiles = RandomFiles(sessionFiles, h.MinFiles, h.MaxFiles)
+	closeFiles = RandomFiles(closeFiles, h.MinFiles, h.MaxFiles)
+	pollFiles = RandomFiles(pollFiles, h.MinFiles, h.MaxFiles)
+
+	var res []*clientpb.HTTPC2PathSegment
+	res = append(res, sessionPaths...)
+	res = append(res, closePaths...)
+	res = append(res, pollPaths...)
+	res = append(res, sessionFiles...)
+	res = append(res, closeFiles...)
+	res = append(res, pollFiles...)
+	return res
+}
+
+func RandomFiles(httpC2PathSegments []*clientpb.HTTPC2PathSegment, minFiles int32, maxFiles int32) []*clientpb.HTTPC2PathSegment {
+	if minFiles < 1 {
+		minFiles = 1
+	}
+	return randomSample(httpC2PathSegments, minFiles, maxFiles)
+}
+
+func RandomPaths(httpC2PathSegments []*clientpb.HTTPC2PathSegment, minPaths int32, maxPaths int32) []*clientpb.HTTPC2PathSegment {
+	return randomSample(httpC2PathSegments, minPaths, maxPaths)
+}
+
+func randomSample(values []*clientpb.HTTPC2PathSegment, min int32, max int32) []*clientpb.HTTPC2PathSegment {
+	count := int32(insecureRand.Intn(len(values)))
+	if count < min {
+		count = min
+	}
+	if max < count {
+		count = max
+	}
+	var sample []*clientpb.HTTPC2PathSegment
+	for i := 0; int32(len(sample)) < count; i++ {
+		index := (count + int32(i)) % int32(len(values))
+		sample = append(sample, values[index])
+	}
+	return sample
+}
diff --git a/server/generate/binaries.go b/server/generate/binaries.go
index 108f5b01f1..458973f700 100644
--- a/server/generate/binaries.go
+++ b/server/generate/binaries.go
@@ -355,7 +355,7 @@ func renderSliverGoCode(name string, otpSecret string, config *clientpb.ImplantC
 	}
 
 	buildLog.Debugf("Generating new sliver binary '%s'", name)
-
+	pbC2Implant = models.RandomizeImplantConfig(pbC2Implant, config.GOOS, config.GOARCH)
 	sliversDir := GetSliversDir() // ~/.sliver/slivers
 	projectGoPathDir := filepath.Join(sliversDir, config.GOOS, config.GOARCH, filepath.Base(name))
 	if _, err := os.Stat(projectGoPathDir); os.IsNotExist(err) {