diff --git a/src/core/Cline.ts b/src/core/Cline.ts
index 3b221eb784..7d7bedcabd 100644
--- a/src/core/Cline.ts
+++ b/src/core/Cline.ts
@@ -3288,12 +3288,7 @@ export class Cline {
 				]),
 			)
 		} catch (err) {
-			this.providerRef
-				.deref()
-				?.log(
-					`[checkpointDiff] Encountered unexpected error: $${err instanceof Error ? err.message : String(err)}`,
-				)
-
+			this.providerRef.deref()?.log("[checkpointDiff] disabling checkpoints for this task")
 			this.checkpointsEnabled = false
 		}
 	}
@@ -3315,12 +3310,7 @@ export class Cline {
 				await this.say("checkpoint_saved", commit.commit)
 			}
 		} catch (err) {
-			this.providerRef
-				.deref()
-				?.log(
-					`[checkpointSave] Encountered unexpected error: $${err instanceof Error ? err.message : String(err)}`,
-				)
-
+			this.providerRef.deref()?.log("[checkpointSave] disabling checkpoints for this task")
 			this.checkpointsEnabled = false
 		}
 	}
@@ -3390,12 +3380,7 @@ export class Cline {
 			// Cline instance.
 			this.providerRef.deref()?.cancelTask()
 		} catch (err) {
-			this.providerRef
-				.deref()
-				?.log(
-					`[restoreCheckpoint] Encountered unexpected error: $${err instanceof Error ? err.message : String(err)}`,
-				)
-
+			this.providerRef.deref()?.log("[checkpointRestore] disabling checkpoints for this task")
 			this.checkpointsEnabled = false
 		}
 	}
diff --git a/src/services/checkpoints/CheckpointService.ts b/src/services/checkpoints/CheckpointService.ts
index 53f0647a67..c2f57a35ab 100644
--- a/src/services/checkpoints/CheckpointService.ts
+++ b/src/services/checkpoints/CheckpointService.ts
@@ -132,19 +132,59 @@ export class CheckpointService {
 		stashSha: string
 		force?: boolean
 	}) {
-		if (force) {
-			await this.git.checkout(["-f", this.mainBranch])
-		} else {
-			await this.git.checkout(this.mainBranch)
+		let currentBranch = await this.git.revparse(["--abbrev-ref", "HEAD"])
+
+		if (currentBranch !== this.mainBranch) {
+			if (force) {
+				try {
+					await this.git.checkout(["-f", this.mainBranch])
+				} catch (err) {
+					this.log(
+						`[restoreMain] failed to force checkout ${this.mainBranch}: ${err instanceof Error ? err.message : String(err)}`,
+					)
+				}
+			} else {
+				try {
+					await this.git.checkout(this.mainBranch)
+				} catch (err) {
+					this.log(
+						`[restoreMain] failed to checkout ${this.mainBranch}: ${err instanceof Error ? err.message : String(err)}`,
+					)
+
+					// Escalate to a forced checkout if we can't checkout the
+					// main branch under nor
+					currentBranch = await this.git.revparse(["--abbrev-ref", "HEAD"])
+
+					if (currentBranch !== this.mainBranch) {
+						await this.git.checkout(["-f", this.mainBranch]).catch(() => {})
+					}
+				}
+			}
+		}
+
+		currentBranch = await this.git.revparse(["--abbrev-ref", "HEAD"])
+
+		if (currentBranch !== this.mainBranch) {
+			throw new Error(`Unable to restore ${this.mainBranch}`)
 		}
 
 		if (stashSha) {
 			this.log(`[restoreMain] applying stash ${stashSha}`)
-			await this.git.raw(["stash", "apply", "--index", stashSha])
+
+			try {
+				await this.git.raw(["stash", "apply", "--index", stashSha])
+			} catch (err) {
+				this.log(`[restoreMain] Failed to apply stash: ${err instanceof Error ? err.message : String(err)}`)
+			}
 		}
 
-		this.log(`[restoreMain] restoring from ${branch}`)
-		await this.git.raw(["restore", "--source", branch, "--worktree", "--", "."])
+		this.log(`[restoreMain] restoring from ${branch} branch`)
+
+		try {
+			await this.git.raw(["restore", "--source", branch, "--worktree", "--", "."])
+		} catch (err) {
+			this.log(`[restoreMain] Failed to restore branch: ${err instanceof Error ? err.message : String(err)}`)
+		}
 	}
 
 	public async saveCheckpoint(message: string) {
@@ -172,15 +212,13 @@ export class CheckpointService {
 		 */
 		try {
 			await this.git.add(["-A"])
-			const status = await this.git.status()
-			this.log(`[saveCheckpoint] status: ${JSON.stringify(status)}`)
 		} catch (err) {
+			this.log(
+				`[saveCheckpoint] failed in stage stash phase: ${err instanceof Error ? err.message : String(err)}`,
+			)
 			await this.git.checkout(["-f", this.mainBranch])
 			await this.git.branch(["-D", stashBranch]).catch(() => {})
-
-			throw new Error(
-				`[saveCheckpoint] Failed in stage stash phase: ${err instanceof Error ? err.message : String(err)}`,
-			)
+			throw err
 		}
 
 		/**
@@ -194,15 +232,15 @@ export class CheckpointService {
 		 */
 		try {
 			// TODO: Add a test to see if empty commits break this.
-			const tempCommit = await this.git.commit(message, undefined, { "--no-verify": null })
-			this.log(`[saveCheckpoint] tempCommit: ${message} -> ${JSON.stringify(tempCommit)}`)
+			const stashCommit = await this.git.commit(message, undefined, { "--no-verify": null })
+			this.log(`[saveCheckpoint] stashCommit: ${message} -> ${JSON.stringify(stashCommit)}`)
 		} catch (err) {
+			this.log(
+				`[saveCheckpoint] failed in stash commit phase: ${err instanceof Error ? err.message : String(err)}`,
+			)
 			await this.git.checkout(["-f", this.mainBranch])
 			await this.git.branch(["-D", stashBranch]).catch(() => {})
-
-			throw new Error(
-				`[saveCheckpoint] Failed in stash commit phase: ${err instanceof Error ? err.message : String(err)}`,
-			)
+			throw err
 		}
 
 		/**
@@ -219,12 +257,10 @@ export class CheckpointService {
 		try {
 			diff = await this.git.diff([latestSha, stashBranch])
 		} catch (err) {
+			this.log(`[saveCheckpoint] failed in diff phase: ${err instanceof Error ? err.message : String(err)}`)
 			await this.restoreMain({ branch: stashBranch, stashSha, force: true })
 			await this.git.branch(["-D", stashBranch]).catch(() => {})
-
-			throw new Error(
-				`[saveCheckpoint] Failed in diff phase: ${err instanceof Error ? err.message : String(err)}`,
-			)
+			throw err
 		}
 
 		if (!diff) {
@@ -249,12 +285,10 @@ export class CheckpointService {
 			await this.git.reset(["--hard", this.mainBranch])
 			this.log(`[saveCheckpoint] reset ${this.hiddenBranch}`)
 		} catch (err) {
+			this.log(`[saveCheckpoint] failed in reset phase: ${err instanceof Error ? err.message : String(err)}`)
 			await this.restoreMain({ branch: stashBranch, stashSha, force: true })
 			await this.git.branch(["-D", stashBranch]).catch(() => {})
-
-			throw new Error(
-				`[saveCheckpoint] Failed in reset phase: ${err instanceof Error ? err.message : String(err)}`,
-			)
+			throw err
 		}
 
 		/**
@@ -289,17 +323,18 @@ export class CheckpointService {
 			this.currentCheckpoint = commit
 			this.log(`[saveCheckpoint] cherry-pick commit = ${commit}`)
 		} catch (err) {
+			this.log(
+				`[saveCheckpoint] failed in cherry pick phase: ${err instanceof Error ? err.message : String(err)}`,
+			)
 			await this.git.reset(["--hard", latestSha]).catch(() => {})
 			await this.restoreMain({ branch: stashBranch, stashSha, force: true })
 			await this.git.branch(["-D", stashBranch]).catch(() => {})
-
-			throw new Error(
-				`[saveCheckpoint] Failed in cherry pick phase: ${err instanceof Error ? err.message : String(err)}`,
-			)
+			throw err
 		}
 
 		await this.restoreMain({ branch: stashBranch, stashSha })
 		await this.git.branch(["-D", stashBranch])
+		this.log(`[saveCheckpoint] saved checkpoint ${commit}`)
 
 		return { commit }
 	}