The blockade of Kakraphoon Island on April 19th, 2008, involved three active main flags. Shadows Of Sage and Good Grief competed fully, while Blackhearted didn’t compete much, only racking up a few points per round. The three flags involved in the blockade agreed to use only war brigs and smaller ships. This agreement was featured in Shadows Of Sage's intent post, as well as Good Grief's. The theme was the flags having "lost" the frigs, or having them filled to the rim with damage/bilge. Blackhearted did not post an intent.

Good Grief used the crew Charlie’s Bananas of the flag Pirates Inc., as they usually do for blockades. Shadows Of Sage used the crew Avengers of Me Wrath also Johanson's crew, while Blackhearted jobbed out of Black Out, Jelleblackie's crew. Crazee and the Good Grief leadership decided to use this blockade as a training blockade for their officers. Some pirates, such as Lupeloca, Scurvycrab, Crazee and Bullseyebud were not permitted to take part in anything other than pre-blockade activities and preparation. Good Grief used the jobbing contacts JobGG and Opsat, and Shadows Of Sage used JobSoS to this capacity. Blackhearted jobbed off the pillage notice board, a move that was mostly ignored politically.

Burninator was the admiral for Good Grief and Johanson admiral/navigated for Shadows of Sage. Admiral for Blackhearted was most likely Jelleblackie, their monarch. The blockade did not feature such usual rock stars like Wazzy, and Kneiss, but used in flag talent. The moments leading to the blockade was very tense, with the flags scrambling to fill ships and get ready, but finally, at twelve noon, the blockade began.

Round one began with the three flags looking pretty strong. Shadows Of Sage began by fielding two brigs and a baghlah. Good Grief brought in two brigs and dhow, while Brokenhearted took in a brig and a dhow. The points in round one were scattered, but there was one "main" cluster worth eight points, and the board had medium amounts of obstacles. The flags brought many more ships in when their ships sank or more jobbers arrived, like Good Grief quickly bringing in a baghlah. Brokenhearted never had more than two ships on board, most notably a sloop that lasted almost the entire round and racked up most of Brokenhearted’s points. Soon SoS fielded another brig and the round reached its peak about twenty minutes in. Good Grief sunk a brig to dominate the eight-point cluster. SoS quickly lost two brigs, and Good Grief took a substantial lead. Most of the three flags' forces were centered on the eight-point cluster, with some minor battles being fought in other, smaller, clusters.

With twenty minutes left in the blockade, SoS' allies, League of Light, fielded a fifty-seven-man war frig, breaking the no-frig rule. It took control of the main cluster, sinking many Grief brigs. However, in an outside four-point cluster a Brokenhearted brig helped a Good Grief baghlah kill off two Shadows of Sage war brigs to take control of that cluster. Shadows of Sage, mainly using the frig, dominated the big point cluster at the end of round one, but Good Grief still managed to sneak away with the win.

The beginning of round two started off quite differently to round one. Good Grief got angry at SoS for breaking the no-frig rule, so Good Grief filled up a frig of their own with forty-three and went in. They also fielded a war brig. Shadows brought in a baghlah and a war brig, with more to come later. Brokenhearted did not compete this round, save for a bit towards the end. The points were very scattered this round, with the biggest cluster a four-pointer. Good Grief used the frig’s massive might ring to grab two two-pointers and took an early lead. Ten minutes later, Brokenhearted brought in a brig and started harassing the Shadows of Sage ships.

The frig that GG had brought in was running out of jobbers fast, and was soon sunk by the LoL war frig, which took a bit of time to reload jobbers. Good Grief quickly fielded another brig to cover the four pointer, but the brig was sunk very quickly, and Shadows of Sage took the lead about thirty minutes in. Good Grief had become out jobbed, but put in a baghlah, which was very ineffective. Seemingly done with the blockade, the LoL war frig departed the board.

Midway through the round, Good Grief had a baghlah and a brig on the board, which were being slightly out-navved. SoS had two brigs and a baghlah on the board, which were covering most points. Brokenhearted had a sloop sitting on a one-pointer. Towards the end of the round Victorious Secret brought in a fifty-man war frig, which harassed the Good Grief ships to no end. Undeclared brought in a sloop, and spent a few turns battling with the frig when the frig moved on. Near the end of the round, the Victorious Secret frig dominated, sinking two Good Grief ships, while not touching anything else. Good Grief brought in a brig and a baghlah but mostly focused on regrouping for round three.

Round three marked the decline of Good Grief’s chances for the blockade. Brokenhearted brought in a sloop and a dhow. Good Grief filled a brig, two dhows and baghlah, and SoS managed two brigs and a dhow. Victorious Secret brought in the same frig from round three. The Victorious Secret ship attacked Good Grief's dhows, chasing one clear across the board before sinking it. The board was a frig-style board, with one main point cluster of eleven points near each other. There was no other big cluster outside of that.

Two Good Grief brigs and two SoS brigs battled it out at the main point cluster, with neither side giving for a while. There were many small ships on the board. The total count was three sloops, two dhows, a baghlah and a brig halfway through the round. SoS had taken an early lead. Soon after, Good Grief representatives contacted Jelleblackie and arranged a peace treaty between Good Grief and Blackhearted, in both flags' best intrests. Grief could target their "real" enemy, Shadows Of Sage, and Blackhearted's sloops would not have to worry about Good Grief.

Midround, the ship count was as follows: SoS had three brigs, Good Grief had two brigs and Blackhearted had two sloops. Victorious Secret's frig was still at large and was beating up on Good Grief badly. SoS had taken complete control of the round, and with Good Grief's hopes small, they decided to work with SoS to take down Victorious Secret. At one point six brigs were focused on the sole war frigate, but it still evaded them all. With fourteen ships on board, the twenty-minute mark of round three had the most ships on board the entire blockade. Almost all of them were focused on the main cluster. Victorious Secret was being swarmed by ships from both sides, but the frigate was navigating very well and was able to sink a few ships and escape much harm. Finally, as the round was coming to a close, two Good Grief ships and two Shadow ships cornered the lone frig outside of a whirlpool and sunk it. Shadows of Sage had taken the round in a rout.

The last round was a lot like a flag-sit, without there being any major competition. Shadows of Sage brought in two brigs and a baghlah, while Good Grief fielded two brigs to begin the round. Blackhearted did not contend. Victorious Secret had another frigate, which they used again to target Good Grief ships. Good Grief was very much out-jobbed, and were only in it to provide Shadows some competition. The board did not have a main cluster, and instead one brig from each side at a time fought it out in different clusters. Good Grief pulled out about halfway in, a Shadows of Sage took the round and the victory.

The blockade was pretty good-natured, and there was not much drama afterwards. Good Grief put a war declaration on League of Light, but it was redacted after Johanson issued a public apology saying that is was a communication error. The blockade was helpful to both sides, in that Good Grief could train officers, and Shadows could do that and they got an island, so there was not much complaining from either blockade team.