Slitherine

The Southwestern Front has been annihilated more or less. However, parts of the reinforcements allocated to the Southern Front have started a supporting operation: it is planned to bypass/outflank the current position of Army Group South and to eventually encircle the Axis troops between Kiev and Lutsk. Hopefully, the troops at Kiev are able to hold out…
Given the overwhelming Axis pressure against its lines, the Southern Front is also retreating now (slowly though).

North Africa:
Derna and Benghazi have been blocked by British warships to avoid additional Italian reinforcements showing up in Libya. British troops are heading west now…
English Channel:
A German submarine has been stopped southwest of Plymouth.
North Sea:
At the same time, the British Home Fleet is sailing east towards the Kiel Canal. It is planned to enter the Baltic Sea and to support potential future Soviet operations along the Baltic coast. The second aircraft carrier of the British Mediterranean Fleet should have been sent north as well, i.e. to support fighter plane transfers from the UK to the Soviet Union. However, the journey through the Atlantic might have required too many supporting resources and might have taken too long to be effective in the end.

Turn 7 – 20 September 1941
Weather: clear and dry

Great Patriotic War:
Again, heavy fighting in the area of the Northwestern Front!
The planned outflanking operation between Southern Bug River and Dniester River had to be stopped due to the sudden appearance of strong German tank forces… They are now also threatening the weak northern flank of the Southern Front around Odessa.

Malta:
The British Mediterranean Fleet arrived at the Strait of Sicily.
Western Europe:
The Royal Air Force is conducting air raids over Germany.
British warships are crossing the unguarded Kiel Canal, bypassing the Skagerrak.

Turn 8 – 5 October 1941
Weather: clear and dry

Great Patriotic War:
Dvinsk could be recaptured by the Northwestern Front. Other than that the (infantry) forces of the Northwestern Front are waiting for the next German attack… and for more reinforcements or at least for bad weather…
German tank and AT forces have been spotted north of Minsk. However, the Soviet front line has been stabilized by now. Mostly light reinforcements are coming in slowly though.
Malta:
Also the situation around Malta seems almost decided... The British Mediterranean Fleet is planning to take control of the area again and then sail further east to support the transfer of British planes from Libya towards the Aegean and then the Black Sea.

Turn 9 – 20 October 1941
Weather: rain and dry

Great Patriotic War:
With bad weather setting in, the German advance north of Minsk seems losing steam already!
Further south, some Soviet infantry units are marching slowly through the Pripet Marshes towards Brest.
Exhausted German forces reached the fortifications in the outskirts of Kiev!

It seems German tank forces are pressing for a decision northwest of Odessa.
At the same time, partisans are close to Bucharest and the Romanian oilfield already!

North Africa:
The decision has been made in North Africa as well. Fighting is expected to stop within a few days!
Malta:
Furthermore, the siege of Malta has finally ended, too!
Norway:
British destroyers are heading towards Trondheim. It would be important to stop Swedish iron ore shipments to Germany soon.

Turn 10 – 4 November 1941
Weather: rain and muddy

Overall situation:
The overall situation looks promising despite severe losses in men and equipment. In addition, critical supply and logistics problems persist as well.
Nonetheless, the Red Army was able to slow down (or even halt) the advance of the Axis forces along the entire front line. Currently, the forward edge of the battle area runs from north to south along a line Pskov-Dvinsk-Minsk-Kiev-Odessa. Based on the overall situation, the Stavka is confident that it can initiate large-scale offensive operations latest by spring.
In addition, North Africa, the Mediterranean Sea and Malta remain under full Allied control and the situation in Western Europe is stable as well.
On the other hand, the Soviet Air Force is still inferior to the Luftwaffe and the British Royal Air Force planes are still too far away from the main combat operations in the east. The British Royal Air Force has air supremacy in Western Europe, North Africa and Malta.
The casualties stand as follows:

Great Patriotic War:
The Northern Front has full control over southern Finland and Karelia, all combat operations have been stopped.
After severe losses, the Northwestern Front had to withdraw behind the Velikaya River but managed to repel several attacks of Army Group North since it occupied new defensive positions.
Given its geographical location, the Western Front was on the main axis of attack by the German Army Group Center and the war started disastrously for the Western Front. Nonetheless, it was able to establish a new stable front line around Minsk. Based on this, Orsha and Smolensk should be save.

The Southwestern Front suffered severe losses as well. However, it has been rebuilt to some extent and more importantly, it was able to slow down the German advance so the Soviet reserves east of Kiev could be fully resupplied and mobilized.
The Southern Front has been holding the line despite continued Axis attacks and heavy losses as well. With newly arriving reserves, it envisions to go on the offensive to seize the vital Romanian oilfield soon.

North Africa:
North Africa is under full Allied control. The British Mediterranean Fleet is planning to attack the Axis forces on the island of Crete. Access to Maleme airfield would be critical to help transfer planes to the Soviet Union.
Malta:
Malta remains British and also the port city of Tripoli has been blocked by British warships until British ground units arrive from Libya.
Northern Europe:
North and Baltic Sea are dominated by British warships as well.

Turn 11 – 19 November 1941
Weather: cloudy and muddy

Great Patriotic War:
The Northwestern Front seems gaining the upper hand, finally?
Standstill at Minsk. Stavka hopes that new reserves sent to the area can make a difference soon.
However, also the Wehrmacht is still sending additional troops from Brest to Minsk to reinforce its Army Group Center.

South of the Pripet Marshes, the way west towards Lutsk seems almost open. Remaining Axis troops around Zhitomir have been cut off and are exhausted.
Also northwest of Odessa, German and Romanian tank forces have been weakened significantly.

Still no breakthrough at Galati though… so close (to the Romanian oilfield), no matter how far!
Can the partisans make a difference? They almost reached Varna and Bucharest from the southwest…
Crete:
Heraklion could be seized by Greek partisans while British warships arrived at Maleme airfield... This could be now the chance to liberate the island and take control of the airport.

Turn 12 – 4 December 1941
Weather: snow and frozen

Great Patriotic War:
In the northwest, Soviet forces started their winter offensive directed at the remaining German troops in the area as well as at Dvinsk and Riga.
Also around Minsk, more and more Soviet forces can be gathered to start the decisive offensive very soon.
Attack on Galati, the frozen rivers in winter increase the mobility of the Soviet forces in the area.

Crete:
The air defense of Maleme airport has been eliminated by naval gunfire already. Now the remaining German troops will be weakened before the partisans can finally seize the airstrip. At the same time, British aircraft carriers are moving into the Aegean to extend the envisioned air bridge towards Thessaloniki. Additional German forces are watching off the main Greek coast, well… all that they can do at the moment…
North Africa:
Finally, exhausted British forces have reached Tripoli. The war in North Africa is over!
Baltic Sea:
British warships reached the Danzig Bay.

Turn 13 – 19 December 1941
Weather: snow and frozen

Great Patriotic War:
It seems German forces haven’t been equipped with adequate winter clothing? On the contrary to this disastrous planning, the Western Front could mobilize new Siberian infantry with skis!
Zhitomir and Rowno have been recaptured and the German forces in the area have given up!
Also Galati and Constanta have been seized. In addition, partisans are already at the gates of Bucharest.

Crete:
The British Mediterranean Fleet is optimistic about its attack on Maleme airport.
Norway:
Trondheim remains in German hands. However, British destroyers are blocking the ports in the area, including Namsos.

this seems way too easy for the allies...not sure how you can increase the difficulty...thanks for laying this out